Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB000197
Identification
Name: NAD
Description:NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed)
Structure
Thumb
Synonyms:
  • β-nicotinamide adenine dinucleotide
  • 3-Carbamoyl-1-b-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt
  • 3-Carbamoyl-1-b-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphoric acid inner salt
  • 3-Carbamoyl-1-b-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt
  • 3-Carbamoyl-1-b-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphoric acid inner salt
  • 3-Carbamoyl-1-b-δ-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt
  • 3-Carbamoyl-1-b-δ-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphoric acid inner salt
  • 3-Carbamoyl-1-beta-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt
  • 3-Carbamoyl-1-beta-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphoric acid inner salt
  • 3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt
  • 3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphoric acid inner salt
  • 3-Carbamoyl-1-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate
  • 3-Carbamoyl-1-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphoric acid
  • 3-Carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate
  • 3-Carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphoric acid
  • 3-Carbamoyl-1-β-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt
  • 3-Carbamoyl-1-β-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphoric acid inner salt
  • 3-Carbamoyl-1-β-δ-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt
  • 3-Carbamoyl-1-β-δ-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphoric acid inner salt
  • 3-Carbamoyl-1-δ-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate
  • 3-Carbamoyl-1-δ-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphoric acid
  • Adenine-nicotinamide dinucleotide
  • b-Diphosphopyridine nucleotide
  • b-NAD
  • b-Nicotinamide adenine dinucleotide
  • b-Nicotinamide adenine dinucleotide trihydrate
  • b-Nicotinamide adenine dinucleotide trihydric acid
  • Beta-Diphosphopyridine nucleotide
  • Beta-NAD
  • Beta-Nicotinamide adenine dinucleotide
  • Beta-Nicotinamide adenine dinucleotide trihydrate
  • Beta-Nicotinamide adenine dinucleotide trihydric acid
  • CO-I
  • Codehydrase I
  • Codehydrogenase I
  • Coenzyme I
  • Cozymase
  • Cozymase I
  • Diphosphopyridine nucleotide
  • Diphosphopyridine nucleotide oxidized
  • DPN
  • DPN+
  • DPN-ox
  • Endopride
  • NAD
  • NAD trihydrate
  • NAD trihydric acid
  • NAD+
  • NAD-ox
  • NAD-oxidized
  • Nicotinamide adenine dinucleotide
  • Nicotinamide adenine dinucleotide oxidized
  • Nicotinamide dinucleotide
  • Nicotineamide adenine dinucleotide
  • Oxidized diphosphopyridine nucleotide
  • Pyridine nucleotide diphosphate
  • Pyridine nucleotide diphosphoric acid
  • [(3S,2R,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3S,2R,4R,5R)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate
  • [(3S,2R,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3S,2R,4R,5R)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphoric acid
  • [adenylate-32-P]-NAD
  • [Adenylic acid-32-P]-nad
  • β-Diphosphopyridine nucleotide
  • β-NAD
  • β-Nicotinamide adenine dinucleotide
  • β-Nicotinamide adenine dinucleotide trihydrate
  • β-Nicotinamide adenine dinucleotide trihydric acid
Chemical Formula: C21H28N7O14P2
Average Molecular Weight: 664.433
Monoisotopic Molecular Weight: 664.116946663
InChI Key: BAWFJGJZGIEFAR-NNYOXOHSSA-O
InChI:InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
CAS number: 53-84-9
IUPAC Name:1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1???pyridin-1-ylium
Traditional IUPAC Name: 1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1???pyridin-1-ylium
SMILES:NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class (5'->5')-dinucleotides
Sub ClassNot Available
Direct Parent (5'->5')-dinucleotides
Alternative Parents
Substituents
  • (5'->5')-dinucleotide
  • Purine nucleotide sugar
  • Purine ribonucleoside diphosphate
  • Nicotinamide-nucleotide
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Pyridine carboxylic acid or derivatives
  • Purine
  • Nicotinamide
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Pyridinium
  • Pyridine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 140.0-142.0 °C
Experimental Properties:
PropertyValueSource
Water Solubility:752.5 mg/mL [HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.81 mg/mLALOGPS
logP-1.2ALOGPS
logP-10ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area318.26 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity142 m3·mol-1ChemAxon
Polarizability55.86 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
1-Deoxy-D-xylulose 5-phosphate + NAD + O-Phospho-4-hydroxy-L-threonine > Carbon dioxide + Hydrogen ion +2 Water + NADH + Pyridoxine 5'-phosphate + Phosphate
Coenzyme A + NAD + Pyruvic acid > Acetyl-CoA + Carbon dioxide + NADH
alpha-Ketoglutarate + Coenzyme A + NAD > Carbon dioxide + NADH + Succinyl-CoA
Acetaldehyde + Coenzyme A + NAD <> Acetyl-CoA + Hydrogen ion + NADH
Tartronate semialdehyde + Hydrogen ion + NADH <> Glyceric acid + NAD
Flavin Mononucleotide + Hydrogen ion + NADH > FMNH + NAD
Hydrogen ion + NADH + Oxygen + Uracil > NAD + Ureidoacrylate peracid
Hydrogen ion + Hydroxypyruvic acid + NADH > Glyceric acid + NAD
Ethanol + NAD <> Acetaldehyde + Hydrogen ion + NADH
NADH + NADP + 2 Hydrogen ion >2 Hydrogen ion + NAD + NADPH
D-Lactic acid + NAD <> Hydrogen ion + NADH + Pyruvic acid
Dihydrouracil + NAD <> Hydrogen ion + NADH + Uracil
2-Demethylmenaquinone 8 + 4 Hydrogen ion + NADH > 2-Demethylmenaquinol 8 + NAD +3 Hydrogen ion
4 Hydrogen ion + NADH + Ubiquinone-8 > NAD + Ubiquinol-8 +3 Hydrogen ion
4 Hydrogen ion + Menaquinone 8 + NADH > Menaquinol 8 + NAD +3 Hydrogen ion
IscS with bound sulfur + MoaD Protein with bound AMP + NADH > Adenosine monophosphate + IscS sulfur acceptor protein + MoaD Protein with thiocarboxylate + NAD
trans-Cinnamic acid + Hydrogen ion + NADH + Oxygen > cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD
Hydrogen ion + NADH + Oxygen + Hydrocinnamic acid > Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD
Hydrogen ion + NADH + 2 Nitric oxide > Water + Nitrous oxide + NAD
Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine
Water + NAD + Xanthine <> Hydrogen ion + NADH + Uric acid
Glycine + NAD + Tetrahydrofolic acid > Carbon dioxide + 5,10-Methylene-THF + NADH + Ammonium
D-Erythrose 4-phosphate + Water + NAD <> 4-Phospho-D-erythronate +2 Hydrogen ion + NADH
5 Hydrogen ion + 3 NADH + Nitrite >2 Water +3 NAD + Ammonium
Glyoxylic acid + Hydrogen ion + NADH > Glycolic acid + NAD
Acetoacetyl-CoA + Hydrogen ion + NADH <> 3-Hydroxybutyryl-CoA + NAD
3-Oxotetradecanoyl-CoA + Hydrogen ion + NADH <> (S)-3-Hydroxytetradecanoyl-CoA + NAD
3-Oxododecanoyl-CoA + Hydrogen ion + NADH <> (S)-3-Hydroxydodecanoyl-CoA + NAD
3-Oxodecanoyl-CoA + Hydrogen ion + NADH <> (S)-Hydroxydecanoyl-CoA + NAD
3-Oxooctanoyl-CoA + Hydrogen ion + NADH <> (S)-Hydroxyoctanoyl-CoA + NAD
3-Oxohexanoyl-CoA + Hydrogen ion + NADH <> (S)-Hydroxyhexanoyl-CoA + NAD
3-Oxohexadecanoyl-CoA + Hydrogen ion + NADH <> (S)-3-Hydroxyhexadecanoyl-CoA + NAD
3-Oxooctadecanoyl-CoA + Hydrogen ion + NADH <> (S)-3-Hydroxyoctadecanoyl-CoA + NAD
NAD + NADPH <> NADH + NADP
Water + NAD <> Adenosine monophosphate +2 Hydrogen ion + Nicotinamide ribotide + NMN
Adenosine triphosphate + Hydrogen ion + Nicotinamide ribotide + NMN <> NAD + Pyrophosphate
Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Water + Isopentenyl pyrophosphate + NAD
Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Dimethylallylpyrophosphate + Water + NAD
Choline + NAD > Betaine aldehyde + Hydrogen ion + NADH
Betaine aldehyde + Water + NAD <> Betaine +2 Hydrogen ion + NADH
3-(3-Hydroxyphenyl)propanoic acid + Hydrogen ion + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD
3-Hydroxycinnamic acid + Hydrogen ion + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + Water + NAD
D-Glyceraldehyde + Hydrogen ion + NADH <> Glycerol + NAD
S-(Hydroxymethyl)glutathione + NAD <> S-Formylglutathione + Hydrogen ion + NADH
NAD + (S)-Ureidoglycolic acid <> Hydrogen ion + NADH + Oxalureate
6,7-Dihydropteridine + 3 Hydrogen ion + NADH <> NAD + Tetrahydropteridine
(2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + NAD + 2,3-Dihydro-2,3-dihydroxybenzoic acid <> 2-Pyrocatechuic acid + Hydrogen ion + NADH
[4Fe-4S] iron-sulfur cluster + 2 S-Adenosylmethionine + Hydrogen ion + NAD + octanoate (protein bound) > [2Fe-2S] iron-sulfur cluster +2 5'-Deoxyadenosine +2 Iron + lipoate (protein bound) +2 L-Methionine + NADH
NADH + Peroxyaminoacrylate > 3-Aminoacrylate + Water + NAD
L-D-1-Pyrroline-5-carboxylic acid + 2 Water + NAD > L-Glutamate + Hydrogen ion + NADH
2-Demethylmenaquinone 8 + Hydrogen ion + NADH > 2-Demethylmenaquinol 8 + NAD
Hydrogen ion + NADH + Ubiquinone-8 > NAD + Ubiquinol-8
Hydrogen ion + Menaquinone 8 + NADH > Menaquinol 8 + NAD
But-2-enoyl-[acyl-carrier protein] + Hydrogen ion + NADH > Butyryl-ACP (n-C4:0ACP) + NAD
Hydrogen ion + NADH + trans-3-cis-11-vacceoyl-[acyl-carrier protein] > NAD + cis-octadec-11-enoyl-[acyl-carrier protein] (n-C18:1)
Hydrogen ion + NADH + trans-3-cis-5-dodecenoyl-[acyl-carrier protein] > cis-dodec-5-enoyl-[acyl-carrier protein] (n-C12:1) + NAD
Hydrogen ion + NADH + trans-3-cis-7-myristoleoyl-[acyl-carrier protein] > NAD + cis-tetradec-7-enoyl-[acyl-carrier protein] (n-C14:1)
Hydrogen ion + NADH + trans-3-cis-9-palmitoleoyl-[acyl-carrier protein] > cis-hexadec-9-enoyl-[acyl-carrier protein] (n-C16:1) + NAD
Hydrogen ion + NADH + trans-Dec-2-enoyl-[acyl-carrier protein] > Decanoyl-ACP (n-C10:0ACP) + NAD
Hydrogen ion + NADH + trans-Dodec-2-enoyl-[acyl-carrier protein] > Dodecanoyl-ACP (n-C12:0ACP) + NAD
Hydrogen ion + NADH + trans-Hex-2-enoyl-[acyl-carrier protein] > Hexanoyl-ACP (n-C6:0ACP) + NAD
Hydrogen ion + NADH + trans-Hexadec-2-enoyl-[acyl-carrier protein] > NAD + Palmitoyl-ACP (n-C16:0ACP)
Hydrogen ion + NADH + trans-Oct-2-enoyl-[acyl-carrier protein] > NAD + Octanoyl-ACP (n-C8:0ACP)
Hydrogen ion + NADH + trans-octadec-2-enoyl-[acyl-carrier protein] > NAD + Octadecanoyl-ACP (n-C18:0ACP)
Hydrogen ion + NADH + trans-Tetradec-2-enoyl-[acyl-carrier protein] > Myristoyl-ACP (n-C14:0ACP) + NAD
Acetaldehyde + Water + NAD > Acetic acid +2 Hydrogen ion + NADH
Water + NAD + Phenylacetaldehyde <>2 Hydrogen ion + NADH + Benzeneacetic acid
(3S)-3-Hydroxyadipyl-CoA + NAD <> Hydrogen ion + NADH + 3-Oxoadipyl-CoA
Water + Lactaldehyde + NAD + (S)-Lactaldehyde <>2 Hydrogen ion + L-Lactic acid + NADH
Glycolaldehyde + Water + NAD > Glycolic acid +2 Hydrogen ion + NADH
4-Aminobutyraldehyde + Water + NAD <> gamma-Aminobutyric acid +2 Hydrogen ion + NADH
L-Malic acid + NAD > Carbon dioxide + NADH + Pyruvic acid
D-Altronate + NAD <> Hydrogen ion + NADH + 5-Keto-D-gluconate + D-Tagaturonate
Water + NAD + Succinic acid semialdehyde >2 Hydrogen ion + NADH + Succinic acid
NAD + Quinate <> 3-Dehydroquinate +2 Hydrogen ion + NADH
Adenosine triphosphate + Nicotinic acid adenine dinucleotide + Ammonium > Adenosine monophosphate + Hydrogen ion + NAD + Pyrophosphate
Water + NAD + N2-Succinyl-L-glutamic acid 5-semialdehyde <>2 Hydrogen ion + NADH + N-Succinyl-L-glutamate
D-Glyceraldehyde 3-phosphate + NAD + Phosphate <> Glyceric acid 1,3-biphosphate + Hydrogen ion + NADH + 3-phospho-D-glyceroyl phosphate
(R)-Malate + NAD <> Carbon dioxide + NADH + Pyruvic acid
Water + L-Histidinol + 2 NAD >3 Hydrogen ion + L-Histidine +2 NADH
Water + 2 NAD + UDP-Glucose <>3 Hydrogen ion +2 NADH + Uridine diphosphate glucuronic acid + UDP-Glucuronic acid
Galactitol 1-phosphate + NAD <> Hydrogen ion + NADH + D-Tagatose 6-phosphate
NAD + Uridine diphosphate glucuronic acid > Carbon dioxide + NADH + UDP-4-Keto-pyranose
4-Phospho-D-erythronate + NAD <> Hydrogen ion + NADH + 2-Oxo-3-hydroxy-4-phosphobutanoic acid
Water + Inosinic acid + NAD <> Hydrogen ion + NADH + Xanthylic acid
cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD > Trans-2,3-Dihydroxycinnamate + Hydrogen ion + NADH
Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD > 3-(2,3-Dihydroxyphenyl)propionic acid + Hydrogen ion + NADH
NADH + 2 Nitric oxide + 2 Oxygen > Hydrogen ion + NAD +2 Nitrate
Adenosine triphosphate + NAD <> ADP + Hydrogen ion + NADP
Hydrogen ion + Lactaldehyde + NADH <> (S)-Propane-1,2-diol + NAD
3-Phosphoglycerate + NAD > Phosphohydroxypyruvic acid + Hydrogen ion + NADH
L-Malic acid + NAD <> Hydrogen ion + NADH + Oxalacetic acid
Precorrin 2 + NAD > Hydrogen ion + NADH + Sirohydrochlorin
D-Biotin D-sulfoxide + Hydrogen ion + NADH > Biotin + Water + NAD
2 -Dehydro-L-gulonate + Hydrogen ion + NADH > Gluconic acid + NAD
2 -Dehydro-L-gulonate + Hydrogen ion + NADH > D-Galactonate + NAD
2,5-Diketo-D-gluconate + Hydrogen ion + NADH > 5-Keto-D-gluconate + NAD
2,3-Diketo-L-gulonate + Hydrogen ion + NADH > 3-Dehydro-L-gulonate + NAD
Sorbitol-6-phosphate + NAD <> Fructose 6-phosphate + Hydrogen ion + NADH
NAD + L-Threonine <> L-2-Amino-3-oxobutanoic acid + Hydrogen ion + NADH
Water + 2 NAD + UDP-N-Acetyl-D-mannosamine <>3 Hydrogen ion +2 NADH + UDP-N-Acetyl-D-mannosaminouronate
FAD + Hydrogen ion + NADH > FADH2 + NAD
Hydrogen ion + NADH + Riboflavin > NAD + Reduced riboflavin
Hydrogen ion + NADH + Succinic acid semialdehyde <> gamma-Hydroxybutyrate + NAD
2 Hydrogen ion + 5,10-Methylene-THF + NADH > 5-Methyltetrahydrofolic acid + NAD
Acetol + Hydrogen ion + NADH > (R)-Propane-1,2-diol + NAD
Glycerol + NAD <> Dihydroxyacetone + Hydrogen ion + NADH
Aminoacetone + Hydrogen ion + NADH <> 1-Amino-2-propanol + NAD
Hydrogen ion + Pyruvaldehyde + NADH > D-Lactaldehyde + NAD
5-Aminoimidazole ribonucleotide + Water + NAD > 4-Amino-2-methyl-5-phosphomethylpyrimidine +2 Formic acid +3 Hydrogen ion + NADH
5-Keto-D-gluconate + Hydrogen ion + NADH <> D-Galactonate + NAD
D-Mannonate + NAD <> D-Fructuronate + Hydrogen ion + NADH
2 L-Glutamate + NAD <> L-Glutamine + alpha-Ketoglutarate + NADH + Hydrogen ion
2 Glutathione + NAD <> Glutathione disulfide + NADH + Hydrogen ion
NAD + 2 Cob(II)alamin + 2 Water + Hydrogen ion <> NADH +2 Aquacobalamin
NAD + Water <> Adenosine monophosphate + Nicotinamide ribotide
Adenosine triphosphate + NAD <> ADP + NADP
NADP + Water <> Phosphate + NAD
Adenosine triphosphate + Nicotinamide ribotide <> Pyrophosphate + NAD
Adenosine triphosphate + Nicotinic acid adenine dinucleotide + Ammonia <> Adenosine monophosphate + Pyrophosphate + NAD
Pyruvaldehyde + NAD + Water <> Pyruvic acid + NADH + Hydrogen ion
L-Malic acid + NAD <> Pyruvic acid + Carbon dioxide + NADH + Hydrogen ion
(R)-Malate + NAD <> Pyruvic acid + Carbon dioxide + NADH + Hydrogen ion
L-Glutamate + NAD + Water <> alpha-Ketoglutarate + Ammonia + NADH + Hydrogen ion
L-Glutamic-gamma-semialdehyde + NAD + Water <> L-Glutamate + NADH + Hydrogen ion
UDP-Glucose + Water + 2 NAD <> Uridine diphosphate glucuronic acid +2 NADH +2 Hydrogen ion
Formic acid + NAD <> Hydrogen ion + Carbon dioxide + NADH
Primary alcohol + NAD <> Aldehyde + NADH + Hydrogen ion
Glycerol 3-phosphate + NAD <> Dihydroxyacetone phosphate + NADH + Hydrogen ion
Tetrahydrofolic acid + NAD <> Dihydrofolic acid + NADH + Hydrogen ion
Tetrahydrofolic acid + 2 NAD <> Folic acid +2 NADH +2 Hydrogen ion
2-Ketobutyric acid + Carbon dioxide + NADH + Hydrogen ion <> D-Erythro-3-Methylmalate + NAD
D-Glyceraldehyde 3-phosphate + Phosphate + NAD <> Glyceric acid 1,3-biphosphate + NADH + Hydrogen ion
L-Histidinal + Water + NAD <> L-Histidine + NADH + Hydrogen ion
Butanal + Coenzyme A + NAD <> Butanoyl-CoA + NADH + Hydrogen ion
Glycine + Tetrahydrofolic acid + NAD <> 5,10-Methylene-THF + Ammonia + Carbon dioxide + NADH + Hydrogen ion
L-Proline + NAD <> L-D-1-Pyrroline-5-carboxylic acid + NADH + Hydrogen ion
Lactaldehyde + NAD + Water <> L-Lactic acid + NADH + Hydrogen ion
3-Phospho-D-glycerate + NAD <> Phosphohydroxypyruvic acid + NADH + Hydrogen ion
2-Keto-3-deoxy-D-gluconic acid + NAD <> (4S)-4,6-Dihydroxy-2,5-dioxohexanoate + NADH + Hydrogen ion
Dihydrolipoamide + NAD <> Lipoamide + NADH + Hydrogen ion
Prephenate + NAD <> 4-Hydroxyphenylpyruvic acid + Carbon dioxide + NADH + Hydrogen ion
L-Homoserine + NAD <> L-Aspartate-semialdehyde + NADH + Hydrogen ion
Ethylene glycol + NAD <> Glycolaldehyde + NADH + Hydrogen ion
Oxoadipic acid + Coenzyme A + NAD <> Glutaryl-CoA + Carbon dioxide + NADH + Hydrogen ion
(S)-3-Hydroxybutanoyl-CoA + NAD <> Acetoacetyl-CoA + NADH + Hydrogen ion
2 Reduced rubredoxin + NAD <>2 Oxidized rubredoxin + NADH + Hydrogen ion
Retinol + NAD <> Retinal + NADH + Hydrogen ion
Dihydrofolic acid + NAD <> Folic acid + NADH + Hydrogen ion
Propylene glycol + NAD <> Lactaldehyde + NADH + Hydrogen ion
Meso-Tartaric acid + NAD <> 2-Hydroxy-3-oxosuccinate + NADH + Hydrogen ion
D-Altronate + NAD <> 5-Keto-D-gluconate + NADH + Hydrogen ion
Sorbitol-6-phosphate + NAD <> beta-D-Fructose 6-phosphate + NADH + Hydrogen ion
L-Histidinol + NAD <> L-Histidinal + NADH + Hydrogen ion
UDP-N-Acetylmuraminate + NAD <> UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADH + Hydrogen ion
Hydroxyproline + NAD <> Pyrroline hydroxycarboxylic acid + NADH + Hydrogen ion
Dihydrolipoylprotein + NAD <> Lipoylprotein + NADH + Hydrogen ion
Tetrahydrodipicolinate + NAD <> 2,3-Dihydrodipicolinic acid + NADH + Hydrogen ion
Butyryl-[acp] + NAD <> But-2-enoyl-[acyl-carrier protein] + NADH + Hydrogen ion
Pyrroline hydroxycarboxylic acid + NAD + 2 Water <> L-erythro-4-Hydroxyglutamate + NADH + Hydrogen ion
Dodecanoyl-[acyl-carrier protein] + NAD <> trans-Dodec-2-enoyl-[acp] + NADH + Hydrogen ion
(S)-3-Hydroxytetradecanoyl-CoA + NAD <> 3-Oxotetradecanoyl-CoA + NADH
Hexanoyl-[acp] + NAD <> trans-Hex-2-enoyl-[acp] + NADH + Hydrogen ion
Octanoyl-[acp] + NAD <> trans-Oct-2-enoyl-[acp] + NADH + Hydrogen ion
Decanoyl-[acp] + NAD <> trans-Dec-2-enoyl-[acp] + NADH + Hydrogen ion
Tetradecanoyl-[acp] + NAD <> trans-Tetradec-2-enoyl-[acp] + NADH + Hydrogen ion
Hexadecanoyl-[acp] + NAD <> trans-Hexadec-2-enoyl-[acp] + NADH + Hydrogen ion
(S)-3-Hydroxyisobutyrate + NAD <> (S)-Methylmalonic acid semialdehyde + NADH + Hydrogen ion
trans-3-Chloro-2-propene-1-ol + NAD <> trans-3-Chloroallyl aldehyde + NADH + Hydrogen ion
cis-3-Chloro-2-propene-1-ol + NAD <> cis-3-Chloroallyl aldehyde + NADH + Hydrogen ion
4-Chlorobiphenyl + Oxygen + NADH + Hydrogen ion <> cis-2,3-Dihydro-2,3-dihydroxy-4'-chlorobiphenyl + NAD
Biphenyl + Oxygen + NADH + Hydrogen ion <> cis-2,3-Dihydro-2,3-dihydroxybiphenyl + NAD
Ethylbenzene + Oxygen + NADH + Hydrogen ion <> cis-1,2-Dihydro-3-ethylcatechol + NAD
O-Phospho-4-hydroxy-L-threonine + NAD <> 2-Amino-3-oxo-4-phosphonooxybutyrate + NADH + Hydrogen ion
Tartaric acid + NAD <> 2-Hydroxy-3-oxosuccinate + NADH + Hydrogen ion
Hydrocinnamic acid + Oxygen + NADH + Hydrogen ion <> cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD
cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD <> 3-(2,3-Dihydroxyphenyl)propionic acid + NADH + Hydrogen ion
Shikimic acid + NAD <> 3-Dehydro-shikimate + NADH + Hydrogen ion
Bisphenol A + NADH + Hydrogen ion + Oxygen <> 1,2-Bis(4-hydroxyphenyl)-2-propanol + NAD + Water
2,2-Bis(4-hydroxyphenyl)-1-propanol + NADH + Hydrogen ion + Oxygen <> 2,3-Bis(4-hydroxyphenyl)-1,2-propanediol + NAD + Water
(2-Naphthyl)methanol + NAD <> 2-Naphthaldehyde + NADH + Hydrogen ion
Chloral hydrate + NADH + Hydrogen ion <> Trichloroethanol + NAD + Water
gamma-Glutamyl-gamma-butyraldehyde + NAD + Water <> 4-(Glutamylamino) butanoate + NADH + Hydrogen ion
Enzyme N6-(dihydrolipoyl)lysine + NAD <> Enzyme N6-(lipoyl)lysine + NADH + Hydrogen ion
Uridine diphosphate glucuronic acid + NAD <> UDP-4-Keto-pyranose + Carbon dioxide + NADH + Hydrogen ion
(2E)-Octadecenoyl-[acp] + NADH + Hydrogen ion <> Octadecanoyl-[acyl-carrier protein] + NAD
Trinitrotoluene + 2 NADH + 2 Hydrogen ion <> 4-Hydroxylamino-2,6-dinitrotoluene +2 NAD + Water
Trinitrotoluene + 2 NADH + 2 Hydrogen ion <> 2-Hydroxylamino-4,6-dinitrotoluene +2 NAD + Water
3-Hydroxy-5-methylhex-4-enoyl-CoA + NAD <> 5-Methyl-3-oxo-4-hexenoyl-CoA + NADH + Hydrogen ion
6-Thioinosine-5'-monophosphate + NAD + Water <> 6-Thioxanthine 5'-monophosphate + NADH + Hydrogen ion
2-Phenyl-1,3-propanediol monocarbamate + NAD <> 3-Carbamoyl-2-phenylpropionaldehyde + NADH + Hydrogen ion
4-Hydroxy-5-phenyltetrahydro-1,3-oxazin-2-one + NAD <> 5-Phenyl-1,3-oxazinane-2,4-dione + NADH + Hydrogen ion
Oxoglutaric acid + Coenzyme A + NAD > Succinyl-CoA + Carbon dioxide + NADH
4,6-Dideoxy-4-oxo-dTDP-D-glucose + NADH + Hydrogen ion <> Deoxythymidine diphosphate-L-rhamnose + NAD
Propylene glycol + NAD <> acetol + NADH + Hydrogen ion
L-Galactonate + NAD > Hydrogen ion + D-tagaturonate + NADH
Ureidoacrylate peracid + NADH > 3-ureidoacrylate + NAD + Water
D-Galactose + NAD 3-keto-&beta;-D-galactose + NADH + Hydrogen ion
Hydrogen ion + Nicotinamide ribotide + Adenosine triphosphate <> NAD + Pyrophosphate
3-Isopropylmalate + NAD <> 2-Isopropyl-3-oxosuccinate + NADH + Hydrogen ion
a primary alcohol + NAD <> an aldehyde + NADH + Hydrogen ion
NAD + D-Altronate <> Hydrogen ion + NADH + D-tagaturonate
NAD + (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate > Hydrogen ion + NADH + 2-Pyrocatechuic acid
DNA<sub><i>n</i></sub> + (deoxynucleotides)<sub>(m)</sub> + NAD > (deoxynucleotides)<sub>(m)</sub> + Nicotinamide ribotide + Adenosine monophosphate
histidinal + NAD + Water > Hydrogen ion + L-Histidine + NADH
L-Histidinol + NAD > Hydrogen ion + histidinal + NADH
NAD + 2-Deoxygluconate <> Hydrogen ion + NADH + 3-Dehydro-2-deoxy-D-gluconate
Hydrogen ion + 3-(3-Hydroxyphenyl)propionate + NADH + Oxygen > Water + 3-(2,3-Dihydroxyphenyl)propionic acid + NAD
Adenosine triphosphate + Nicotinic acid adenine dinucleotide + L-Glutamine + Water > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + NAD + L-Glutamate
Hydrogen ion + a ubiquinone + NADH <> a ubiquinol + NAD
menadione + NADH + Hydrogen ion menadiol + NAD
Water + NAD <> Hydrogen ion + Adenosine diphosphate ribose + Niacinamide
Water + NAD > Hydrogen ion + Nicotinamide ribotide + Adenosine monophosphate
NAD + a (3<i>S</i>)-3-hydroxyacyl-CoA > NADH + a 3-oxoacyl-CoA + Hydrogen ion
Water + NAD + Phenylacetaldehyde <> Hydrogen ion + NADH + phenylacetate
Prephenate + NAD > 4-Hydroxyphenylpyruvic acid + Carbon dioxide + NADH
NADH + Copper Hydrogen ion + NAD + Cu<SUP>+</SUP>
an alcohol + Water + NAD < an organic hydroperoxide + NADH + Hydrogen ion
2-hydroxyglutarate + NAD <> Hydrogen ion + Oxoglutaric acid + NADH
3-Hydroxyadipyl-CoA + NAD <> Hydrogen ion + 3-Oxoadipyl-CoA + NADH
Hydrogen ion + Pyruvaldehyde + NADH acetol + NAD
NADH + Hydrogen ion + a menaquinone > a menaquinol + NAD
3-hydroxypropionaldehyde + NAD + Water > Hydrogen ion + 3-Hydroxypropanoate + NADH
Dihydrothymine + NAD <> Thymine + NADH + Hydrogen ion
a quinone + NADH NAD + a semiquinone
N2-Succinyl-L-glutamic acid 5-semialdehyde + NAD + Water > N<SUP>2</SUP>-succinylglutamate + NADH + Hydrogen ion
Trimethylamine N-Oxide + NADH + Hydrogen ion > Trimethylamine + NAD + Water
3-Hydroxyisobutyric acid + NAD <> 2-Aminomalonate semialdehyde + NADH
4-Aminobutyraldehyde + NAD + Water > gamma-Aminobutyric acid + NADH
An alcohol + NAD > an aldehyde or ketone + NADH
Lactaldehyde + NAD + Water > L-Lactic acid + NADH
Glycolaldehyde + NAD + Water > Glycolic acid + NADH
UDP-Glucuronic acid + NAD > UDP-beta-L-Threo-pentapyranos-4-ulose + Carbon dioxide + NADH
N2-Succinyl-L-glutamic acid 5-semialdehyde + NAD + Water > N-Succinyl-L-glutamate + NADH
Betaine aldehyde + NAD + Water > Betaine + NADH
NADH + acceptor > NAD + reduced acceptor
Protein N(6)-(dihydrolipoyl)lysine + NAD > protein N(6)-(lipoyl)lysine + NADH
D-Lactic acid + NAD > Pyruvic acid + NADH
NAD + (deoxyribonucleotide)(n) + (deoxyribonucleotide)(m) > Adenosine monophosphate + NMN + (deoxyribonucleotide)(n+m)
D-Erythrose 4-phosphate + NAD + Water > 4-Phospho-D-erythronate + NADH
Acyl-[acyl-carrier-protein] + NAD > trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADH
(S)-3-hydroxyacyl-CoA + NAD > 3-oxoacyl-CoA + NADH
Formic acid + NAD > Carbon dioxide + NADH
Phenylacetaldehyde + NAD + Water > Benzeneacetic acid + NADH
2 Cob(II)alamin + NAD >2 Aquacobalamin + NADH
(R)-Propane-1,2-diol + NAD > D-Lactaldehyde + NADH
(S)-Propane-1,2-diol + NAD > Lactaldehyde + NADH
D-Glyceraldehyde 3-phosphate + Inorganic phosphate + NAD > 3-phospho-D-glyceroyl phosphate + NADH
Galactitol 1-phosphate + NAD > L-Tagatose-6-phosphate + NADH
Glycerol + NAD > Dihydroxyacetone + NADH
cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD > 3-(2,3-Dihydroxyphenyl)propanoate + NADH
cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD > Trans-2,3-Dihydroxycinnamate + NADH
Reduced ferredoxin + NAD > oxidized ferredoxin + NADH
Hydrocinnamic acid + NADH + Oxygen > cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD
trans-Cinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + NAD
L-Histidinol + Water + 2 NAD > L-Histidine +2 NADH
Inosinic acid + NAD + Water > Xanthylic acid + NADH
2-Keto-3-deoxy-D-gluconic acid + NAD > (4S)-4,6-Dihydroxy-2,5-dioxohexanoate + NADH
3-Isopropylmalate + NAD > Ketoleucine + Carbon dioxide + NADH
L-Malic acid + NAD > Oxalacetic acid + NADH
3-(3-Hydroxyphenyl)propanoic acid + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propanoate + Water + NAD
3-Hydroxycinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + Water + NAD
Mannitol 1-phosphate + NAD > Fructose 6-phosphate + NADH
Adenosine triphosphate + NMN > Pyrophosphate + NAD
Tetrahydropteridine + NAD > 6,7-Dihydropteridine + NADH
Reduced NO reductase rubredoxin + NAD > oxidized NO reductase rubredoxin + NADH
NAD + an acetylprotein > Niacinamide + O-acetyl-ADP-ribose + a protein
NAD + Water > Adenosine monophosphate + NMN
NADH + Quinone > NAD + Hydroquinone
4-Phospho-D-erythronate + NAD > 2-Oxo-3-hydroxy-4-phosphobutanoic acid + NADH
Dihydrouracil + NAD > Uracil + NADH
Dihydrothymine + NAD > Thymine + NADH
FMNH(2) + NAD > Flavin Mononucleotide + NADH
3-Phospho-D-glycerate + NAD > Phosphohydroxypyruvic acid + NADH
D-2-Hydroxyglutaric acid + NAD > Oxoglutaric acid + NADH
Sorbitol-6-phosphate + NAD > Fructose 6-phosphate + NADH
L-Threonine + NAD > L-2-Amino-3-oxobutanoic acid + NADH
UDP-Glucose + 2 NAD + Water > UDP-Glucuronic acid +2 NADH
D-Altronate + NAD > D-tagaturonate + NADH
D-Mannonate + NAD > D-Fructuronate + NADH
UDP-N-Acetyl-D-mannosamine + 2 NAD + Water > UDP-N-Acetyl-D-mannosaminouronate +2 NADH
Xanthine + NAD + Water > Uric acid + NADH
Hypoxanthine + NAD + Water > Xanthine + NADH
Succinic acid semialdehyde + NAD + NADP + Water <> Succinic acid + NADH + NADPH +2 Hydrogen ion
Glyceric acid + NAD + NADP <> Tartronate semialdehyde + NADH + NADPH + Hydrogen ion
Protein dithiol + NAD + NADP <> Protein disulfide + NADH + NADPH + Hydrogen ion
Isopentenyl pyrophosphate + NAD + NADP + Water + Dimethylallylpyrophosphate <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + NADPH + Hydrogen ion
Tetrahydrodipicolinate + NAD + NADP + Water <> (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + NADH + NADPH + Hydrogen ion
Protein N6-(dihydrolipoyl)lysine + NAD <> Protein N6-(lipoyl)lysine + NADH + Hydrogen ion
3-(3-Hydroxyphenyl)propanoic acid + NADH + Hydrogen ion + Oxygen + 3-Hydroxycinnamic acid <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD + Trans-2,3-Dihydroxycinnamate
NADH + Hydrogen ion + Acceptor <> NAD + Reduced acceptor
Quinate + NAD + NADP + Shikimic acid <> 3-Dehydroquinate + NADH + NADPH + Hydrogen ion + 3-Dehydro-shikimate
Dihydrouracil + NAD + Dihydrothymine <> Uracil + NADH + Hydrogen ion + Thymine
NADH + Hydrogen ion + Oxygen + Hydrocinnamic acid <> cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD + Trans-2,3-Dihydroxycinnamate
cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD + cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol <> 3-(2,3-Dihydroxyphenyl)propionic acid + NADH + Hydrogen ion + Trans-2,3-Dihydroxycinnamate
NAD + Hydrogen ion <> NADH
Nitric oxide + 2 Oxygen + NADH + NADPH <>2 Nitrate + NAD + NADP + Hydrogen ion
Sorbitol 6-phosphate + NAD <> Fructose 6-phosphate + NADH + Hydrogen ion
3-Dehydro-L-gulonate + NAD + NADP <> 2,3-Diketo-L-gulonate + NADH + NADPH + Hydrogen ion
Mannitol 1-phosphate + NAD <> Fructose 6-phosphate + NADH + Hydrogen ion
5-Methyltetrahydrofolic acid + NAD + NADP <> 5,10-Methylene-THF + NADH + NADPH + Hydrogen ion
NAD + 2-Amino-3-oxo-4-phosphonooxybutyrate + O-Phospho-4-hydroxy-L-threonine <> 3-Amino-2-oxopropyl phosphate + Carbon dioxide + NADH + Hydrogen ion
3-Isopropylmalate + NAD + 2-Isopropyl-3-oxosuccinate <> Ketoleucine + Carbon dioxide + NADH + Hydrogen ion
S-(Hydroxymethyl)glutathione + NAD + NADP <> S-Formylglutathione + NADH + NADPH + Hydrogen ion
L-Proline + NAD + NADP <> (S)-1-pyrroline-5-carboxylate + NADH + NADPH + Hydrogen ion
Tetrahydropteridine + NAD + NADP <> 6,7-Dihydropteridine + NADH + NADPH + Hydrogen ion
NADH + NADPH + Hydrogen ion + Quinone <> NAD + NADP + Hydroquinone
Acyl-[acyl-carrier protein] + NAD <> trans-2,3-Dehydroacyl-[acyl-carrier protein] + NADH + Hydrogen ion
Primary alcohol + NAD + Secondary alcohol <> Aldehyde + NADH + Hydrogen ion + Ketone
L-Malic acid + NAD + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADH
L-Gulonate + NAD <> D-Fructuronate + NADH + Hydrogen ion
Cholic acid + NAD <> NADH + Hydrogen ion
NAD + Galactitol 1-phosphate <> L-Tagatose-6-phosphate + NADH + Hydrogen ion
NADH + Ubiquinone-1 <> NAD + Ubiquinol-8
(3S)-3-Hydroxyacyl-CoA + NAD <> 3-Oxoacyl-CoA + NADH + Hydrogen ion
NAD + DNA <> Adenosine monophosphate + NMN
(R)-Propane-1,2-diol + (S)-Propane-1,2-diol + NAD <> D-Lactaldehyde + (S)-Lactaldehyde + NADH + Hydrogen ion
3-Phospho-D-glycerate + NAD + D-2-Hydroxyglutaric acid <> Phosphohydroxypyruvic acid + NADH + Hydrogen ion + alpha-Ketoglutarate
Glycerol 3-phosphate + NAD + NADP <> Dihydroxyacetone phosphate + NADH + NADPH + Hydrogen ion
4-Hydroxybutanoic acid + NAD <> Succinic acid semialdehyde + NADH + Hydrogen ion
Gluconic acid + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ion
L-Idonate + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ion
Ammonia + NAD + 3 NADP + 2 Water <> Nitrite + NADH +3 NADPH +5 Hydrogen ion
(S)-Ureidoglycolic acid + NAD + NADP <> Oxalureate + NADH + NADPH + Hydrogen ion
Nitrite + 3 NADH + 5 Hydrogen ion + Nitrite Ammonia +2 Water +3 NAD
(3S)-3-hydroxyacyl-CoA + NAD > NADH + Hydrogen ion + a 3-oxoacyl-CoA?
3-Hydroxybutyryl-CoA + NAD + 3-Hydroxybutyryl-CoA > NADH + Hydrogen ion + Acetoacetyl-CoA + Acetoacetyl-CoA
(S)-Hydroxyoctanoyl-CoA + NAD + (S)-Hydroxyoctanoyl-CoA NADH + Hydrogen ion + 3-Oxooctanoyl-CoA
(S)-3-Hydroxyoctadecanoyl-CoA + NAD > NADH + Hydrogen ion + 3-Oxooctadecanoyl-CoA + 3-Oxooctadecanoyl-CoA
2,3-dihydroxy-2,3-dihydrobenzoate + NAD > 2,3-Dihydroxybenzoic acid + NADH + Hydrogen ion
2,3-dihydroxy-2,3-dihydrobenzoate + NAD > 2-Pyrocatechuic acid + NADH + Hydrogen ion
NAD + 3-Hydroxy-5-methylhex-4-enoyl-CoA > NADH + Hydrogen ion + 5-Methyl-3-oxo-4-hexenoyl-CoA
(3S)-3-Hydroxyadipyl-CoA + NAD > 3-Oxoadipyl-CoA + NADH + Hydrogen ion
Isocitric acid + NAD + Isocitric acid > Oxoglutaric acid + Carbon dioxide + NADH + Hydrogen ion
Oxoglutaric acid + NAD + Coenzyme A > Succinyl-CoA + NADH + Hydrogen ion + Carbon dioxide + Succinyl-CoA
L-Malic acid + NAD + L-Malic acid <> Oxalacetic acid + NADH + Hydrogen ion
Oxoglutaric acid + NAD + Coenzyme A > NADH + Carbon dioxide + Succinyl-CoA + Succinyl-CoA
D-Glyceraldehyde 3-phosphate + NAD + Phosphate + D-Glyceraldehyde 3-phosphate > Glyceric acid 1,3-biphosphate + NADH + Hydrogen ion + Glyceric acid 1,3-biphosphate
N2-Succinyl-L-glutamic acid 5-semialdehyde + Water + NAD >2 Hydrogen ion + NADH + N2-succinylglutamate + N2-succinylglutamate
2,3-Diketo-L-gulonate + NADH + Hydrogen ion + 2,3-Diketo-L-gulonate > 3-Dehydro-L-gulonate + NAD
L-Glutamic-gamma-semialdehyde + NAD + Water >2 Hydrogen ion + NADH + L-Glutamic acid + L-Glutamate
trans-?3-cis-?7-tetradecenoyl-[acp] + Hydrogen ion + NADH > NAD + cis-?7-tetradecenoyl-[acp]?
trans tetradec-2-enoyl-[acp] + Hydrogen ion + NADH > NAD + myristoyl-[acp]
trans-?3-cis-?5-dodecenoyl-[acp] + Hydrogen ion + NADH > cis-?5-dodecenoyl-[acp]? + NAD
trans-?3-cis-?9-hexadecenoyl-[acp] + Hydrogen ion + NADH > NAD + a palmitoleoyl-[acp]?
cis-vaccen-2-enoyl-[acp] + Hydrogen ion + NADH > NAD + a cis-vaccenoyl-[acp]
trans-2-enoyl-[acyl-carrier protein] + Hydrogen ion + NADH > NAD + 2,3,4-saturated fatty acyl-[acp]
crotonyl-[acp] + Hydrogen ion + NADH > NAD + butyryl-[acp]
trans hex-2-enoyl-[acp] + Hydrogen ion + NADH > NAD + hexanoyl-[acyl-carrier-protein]
trans oct-2-enoyl-[acp] + Hydrogen ion + NADH > NAD + Octanoyl-[acyl-carrier protein]
a trans-?2-decenoyl-[acp]? + Hydrogen ion + NADH > NAD + decanoyl-[acp]
trans dodec-2-enoyl-[acp] + Hydrogen ion + NADH > NAD + dodecanoyl-[acp]?
Hydrogen ion + NADH + trans hexadecenoyl-[acp] > NAD + palmitoyl-[acp]
3-Phosphoglyceric acid + NAD + 3-Phosphoglycerate > NADH + Hydrogen ion + Phosphohydroxypyruvic acid
Prephenate + NAD > NADH + Carbon dioxide + 4-hydroxyphenylpyruvate
Water + NAD + Histidinal >2 Hydrogen ion + NADH + L-Histidine + L-Histidine
L-Malic acid + NAD + L-Malic acid > Carbon dioxide + NADH + Pyruvic acid
Galactose 1-phosphate + NAD + Galactose 1-phosphate > NADH + Hydrogen ion + D-tagatofuranose 6-phosphate
NAD + Water + (S)-lactaldehyde + Lactaldehyde > NADH +2 Hydrogen ion + L-Lactic acid + L-Lactic acid
(S)-lactaldehyde + NADH + Hydrogen ion + Lactaldehyde > NAD + Propylene glycol
Nicotinic acid adenine dinucleotide + Water + L-Glutamine + Adenosine triphosphate > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + L-Glutamic acid + NAD + L-Glutamate
Nicotinic acid adenine dinucleotide + Adenosine triphosphate + Ammonium > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + NAD
beta-nicotinamide D-ribonucleotide + Adenosine triphosphate + Hydrogen ion + NMN > Pyrophosphate + NAD
D-Fructuronate + NADH + Hydrogen ion > NAD + D-altronate
D-tagaturonate + NADH + Hydrogen ion + D-Tagaturonate > NAD + D-altronate + D-altronate
UDP-N-acetyl-D-mannosamine + 2 NAD + Water + UDP-N-Acetyl-D-mannosamine > UDP-N-acetyl-α-D-mannosaminuronate +2 NADH +3 Hydrogen ion
UDP-Glucose + 2 NAD + Water > UDP-Glucuronic acid +2 NADH +3 Hydrogen ion
UDP-Glucuronic acid + NAD > Carbon dioxide + NADH + UDP-β-L-threo-pentapyranos-4-ulose
Precorrin-2 + NAD > NADH + Hydrogen ion + Sirohydrochlorin
3-Hydroxycinnamic acid + Hydrogen ion + NADH + Oxygen > NAD + Water + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
Cinnamic acid + NADH + Oxygen <> cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD
NADH + Oxygen + 3-phenylpropanoate <> NAD + cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol
NADH + Oxygen + 3-phenylpropanoate <> NAD + Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol
Copper + NADH > NAD + Cu(+)
Fructose 6-phosphate + NADH + Hydrogen ion + Fructose 6-phosphate <> NAD + Mannitol 1-phosphate
NAD + cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol > NADH + Hydrogen ion + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
L-Threonine + NAD + L-Threonine > Hydrogen ion + NADH + L-2-Amino-3-oxobutanoic acid
NADH + 5 Hydrogen ion + Ubiquinone-1 > Hydrogen ion + NAD + Ubiquinol-1
NADH + 4 Hydrogen ion + 2 Hydrogen ion + menaquinone-8 NAD + Hydrogen ion + Menaquinol 8 + Electron +4 Hydrogen ion
1-Amino-2-propanol + NAD + 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene < NADH + Hydrogen ion + Aminoacetone
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0000029000-870aa620464a4fedbe8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002r-0930610000-ccd233f26036136ba3e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-0900000000-ec77ba41ae7dbcfd08a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00dl-0219003700-2f52e3c5db41066a112cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-0301009000-a3d0c464e56f6e320c80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00dl-0000090000-c18a7719161c63a71938View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0000009000-1dde5b221786fe375304View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0911001000-bd16ca8021ab63e9e290View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-662adda5a00fce5c5017View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-a2724dbab2ca6eb7e8daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00dl-0400090000-19bb49ef6fe960f224d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-006x-0011297400-efee4fe3a4cf024c960aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0028900000-8ec9bcaf25513495b979View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0011953000-577487fb6aff29c77330View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0000009000-e1d0afb4e7926a0f845eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0001092010-1dcbca7a5ffe61f23e50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0028900000-764e3ecea72fe178a87eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0018900000-3b774fba9b96129baa6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0000090000-d4236efb9eec36017416View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
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  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
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  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kim MY, Zhang T, Kraus WL: Poly(ADP-ribosyl)ation by PARP-1: 'PAR-laying' NAD+ into a nuclear signal. Genes Dev. 2005 Sep 1;19(17):1951-67. Pubmed: 16140981
  • Krotz F, Sohn HY, Gloe T, Zahler S, Riexinger T, Schiele TM, Becker BF, Theisen K, Klauss V, Pohl U: NAD(P)H oxidase-dependent platelet superoxide anion release increases platelet recruitment. Blood. 2002 Aug 1;100(3):917-24. Pubmed: 12130503
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  • Orczyk J, Morre DM, Morre DJ: Periodic fluctuations in oxygen consumption comparing HeLa (cancer) and CHO (non-cancer) cells and response to external NAD(P)+/NAD(P)H. Mol Cell Biochem. 2005 May;273(1-2):161-7. Pubmed: 16013451
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
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Synthesis Reference: Hughes, N. A.; Kenner, G. W.; Todd, Alexander. Codehydrogenases. III. Synthesis of diphosphopyridine nucleotide (cozymase) and triphosphopyridine nucleotide. Journal of the Chemical Society (1957), 3733-8.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
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CHEBI ID15846
HMDB IDHMDB00902
Pubchem Compound ID5892
Kegg IDC00003
ChemSpider ID5682
WikipediaNAD
BioCyc IDNAD
EcoCyc IDNAD
Ligand ExpoNAJ