Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB000615
Identification
Name: NADPH
Description:Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.)
Structure
Thumb
Synonyms:
  • 2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide
  • 2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-delta-ribofuranosylnicotinamide
  • 2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-δ-ribofuranosylnicotinamide
  • 2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide
  • 2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-β-δ-ribofuranosylnicotinamide
  • 2'-(Dihydrogen phosphoric acid) 5'-(trihydrogen pyrophosphoric acid) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide
  • 2'-(Dihydrogen phosphoric acid) 5'-(trihydrogen pyrophosphoric acid) adenosine 5'-ester with 1,4-dihydro-1-b-delta-ribofuranosylnicotinamide
  • 2'-(Dihydrogen phosphoric acid) 5'-(trihydrogen pyrophosphoric acid) adenosine 5'-ester with 1,4-dihydro-1-b-δ-ribofuranosylnicotinamide
  • 2'-(Dihydrogen phosphoric acid) 5'-(trihydrogen pyrophosphoric acid) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide
  • 2'-(Dihydrogen phosphoric acid) 5'-(trihydrogen pyrophosphoric acid) adenosine 5'-ester with 1,4-dihydro-1-β-δ-ribofuranosylnicotinamide
  • Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-b-D-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-b-delta-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-b-δ-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-β-D-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-β-δ-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-b-D-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-b-delta-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-b-δ-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-β-D-ribofuranosyl-3-pyridinecarboxamide
  • Adenosine 5'-(trihydrogen diphosphoric acid) 2'-(dihydrogen phosphoric acid) p'-5'-ester with 1,4-dihydro-1-β-δ-ribofuranosyl-3-pyridinecarboxamide
  • B-NADPH
  • b-Nicotinamide-adenine-dinucleotide-phosphate
  • B-Nicotinamide-adenine-dinucleotide-phosphorate
  • B-Nicotinamide-adenine-dinucleotide-phosphoric acid
  • Beta-NADPH
  • beta-Nicotinamide-adenine-dinucleotide-phosphate
  • Beta-Nicotinamide-adenine-dinucleotide-phosphorate
  • Beta-Nicotinamide-adenine-dinucleotide-phosphoric acid
  • Dihydrocodehydrogenase
  • Dihydrocodehydrogenase II
  • Dihydronicotinamide adenine dinucleotide phosphate
  • Dihydronicotinamide adenine dinucleotide phosphate reduced
  • Dihydronicotinamide adenine dinucleotide phosphoric acid
  • Dihydronicotinamide adenine dinucleotide phosphoric acid reduced
  • Dihydronicotinamide adenine dinucleotide-P
  • Dihydrotriphosphopyridine nucleotide
  • Dihydrotriphosphopyridine nucleotide reduced
  • NADP(H)
  • NADP-red
  • NADP-reduced
  • NADPH
  • NADPH+H+
  • NADPH2
  • NADPH2
  • NADPH+H+
  • Nicotinamide adenine dinucleotide phosphate - reduced
  • Nicotinamide adenine dinucleotide phosphoric acid - reduced
  • Nicotinamide-adenine-dinucleotide-phosphate
  • Nicotinamide-adenine-dinucleotide-phosphorate
  • Nicotinamide-adenine-dinucleotide-phosphoric acid
  • Reduced Codehydrase
  • Reduced Codehydrase II
  • Reduced Coenzyme
  • Reduced Coenzyme II
  • Reduced Cozymase
  • Reduced Cozymase II
  • Reduced triphosphopyridine nucleotide
  • TPNH
  • Triphosphopyridine nucleotide reduced
  • β-NADPH
  • β-Nicotinamide-adenine-dinucleotide-phosphate
  • β-Nicotinamide-adenine-dinucleotide-phosphorate
  • β-Nicotinamide-adenine-dinucleotide-phosphoric acid
Chemical Formula: C21H30N7O17P3
Average Molecular Weight: 745.4209
Monoisotopic Molecular Weight: 745.091102105
InChI Key: ACFIXJIJDZMPPO-NCHANQSKSA-N
InChI:InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1
CAS number: 53-57-6
IUPAC Name:{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name: nadph
SMILES:NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine nucleotide sugars
Direct Parent Purine nucleotide sugars
Alternative Parents
Substituents
  • Purine nucleotide sugar
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside 2',5'-bisphosphate
  • Nicotinamide-nucleotide
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • N-substituted nicotinamide
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Dihydropyridinecarboxylic acid derivative
  • Monoalkyl phosphate
  • Dihydropyridine
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Hydropyridine
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Tertiary amine
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Enamine
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.45 mg/mLALOGPS
logP-1.1ALOGPS
logP-7.5ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.66ChemAxon
pKa (Strongest Basic)4.92ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area364.15 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity153.87 m3·mol-1ChemAxon
Polarizability63.54 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
2 flavodoxin semi oxidized + NADPH >2 Flavodoxin reduced + Hydrogen ion + NADP
Hydrogen ion + NADPH + Oxidized Thioredoxin > NADP + Reduced Thioredoxin
2,5-Diketo-D-gluconate + Hydrogen ion + NADPH >2 -Dehydro-L-gulonate + NADP
2-Dehydropantoate + Hydrogen ion + NADPH <> NADP + (R)-Pantoate
Hydrogen ion + Malonic semialdehyde + NADPH > 3-Hydroxypropanoate + NADP
Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP
Hydrogen ion + Hydroxypyruvic acid + NADPH > Glyceric acid + NADP
NADH + NADP + 2 Hydrogen ion >2 Hydrogen ion + NAD + NADPH
Dihydrofolic acid + Hydrogen ion + NADPH <> NADP + Tetrahydrofolic acid
3-Dehydro-shikimate + Hydrogen ion + NADPH <> NADP + Shikimic acid
Adenosine triphosphate + Dehydroglycine + 1-Deoxy-D-xylulose 5-phosphate + Hydrogen ion + IscS with bound sulfur + NADPH > 4-Methyl-5-(2-phosphoethyl)-thiazole + Adenosine monophosphate + Carbon dioxide +2 Water + IscS sulfur acceptor protein + NADP + Pyrophosphate
Water + NADP + Succinic acid semialdehyde >2 Hydrogen ion + NADPH + Succinic acid
FAD + Hydrogen ion + NADPH > FADH2 + NADP
5 Hydrogen ion + 3 NADPH + Sulfite <>3 Water + Hydrogen sulfide +3 NADP
Hydrogen ion + Pyruvaldehyde + NADPH > Acetol + NADP
Hydrogen ion + NADPH + Riboflavin > NADP + Reduced riboflavin
Flavin Mononucleotide + Hydrogen ion + NADPH <> FMNH + NADP
L-Homoserine + NADP <> L-Aspartate-semialdehyde + Hydrogen ion + NADPH
NAD + NADPH <> NADH + NADP
2,3-Dihydrodipicolinic acid + Hydrogen ion + NADPH > NADP + Tetrahydrodipicolinate
Guanosine monophosphate + 2 Hydrogen ion + NADPH > Inosinic acid + NADP + Ammonium
1-Deoxy-D-xylulose 5-phosphate + Hydrogen ion + NADPH <> 2-C-Methyl-D-erythritol-4-phosphate + NADP
L-Glutamic acid 5-phosphate + Hydrogen ion + NADPH > L-Glutamic-gamma-semialdehyde + NADP + Phosphate
Betaine aldehyde + Water + NADP > Betaine +2 Hydrogen ion + NADPH
L-D-1-Pyrroline-5-carboxylic acid + 2 Hydrogen ion + NADPH > NADP + L-Proline
5-Amino-6-(5'-phosphoribosylamino)uracil + Hydrogen ion + NADPH > 5-Amino-6-(5'-phosphoribitylamino)uracil + NADP
5,10-Methylene-THF + NADP <> 5,10-Methenyltetrahydrofolate + NADPH + Hydrogen ion
6,7-Dihydropteridine + 3 Hydrogen ion + NADPH <> NADP + Tetrahydropteridine
3 -oxo-cis-dodec-5-enoyl-[acyl-carrier protein] + Hydrogen ion + NADPH > (R)-3-hydroxy-cis-dodec-5-enoyl-[acyl-carrier protein] + NADP
3 -oxo-cis-myristol-7-eoyl-[acyl-carrier protein] + Hydrogen ion + NADPH > (R)-3-hydroxy-cis-myristol-7-eoyl-[acyl-carrier protein] + NADP
3 -oxo-cis-palm-9-eoyl-[acyl-carrier protein] + Hydrogen ion + NADPH > (R)-3-hydroxy-cis-palm-9-eoyl-[acyl-carrier protein] + NADP
3 -oxo-cis-vacc-11-enoyl-[acyl-carrier protein] + Hydrogen ion + NADPH > (R)-3-hydroxy-cis-vacc-11-enoyl-[acyl-carrier protein] + NADP
3 -Oxodecanoyl-[acyl-carrier protein] + Hydrogen ion + NADPH <> (R)-3-Hydroxydecanoyl-[acyl-carrier protein] + NADP
3 -Oxododecanoyl-[acyl-carrier protein] + Hydrogen ion + NADPH <> (R)-3-Hydroxydodecanoyl-[acyl-carrier protein] + NADP
3 -Oxohexadecanoyl-[acyl-carrier protein] + Hydrogen ion + NADPH <> R-3-hydroxypalmitoyl-[acyl-carrier protein] + NADP
3 -Oxohexanoyl-[acyl-carrier protein] + Hydrogen ion + NADPH <> (R)-3-Hydroxyhexanoyl-[acyl-carrier protein] + NADP
3 -Oxooctadecanoyl-[acyl-carrier protein] + Hydrogen ion + NADPH <> (R)-3-Hydroxyoctadecanoyl-[acyl-carrier protein] + NADP
3 -Oxooctanoyl-[acyl-carrier protein] + Hydrogen ion + NADPH <> (R)-3-Hydroxyoctanoyl-[acyl-carrier protein] + NADP
3 -Oxotetradecanoyl-[acyl-carrier protein] + Hydrogen ion + NADPH <> (R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + NADP
Acetoacetyl-ACP + Hydrogen ion + NADPH <> (3R)-3-Hydroxyacyl-[acyl-carrier protein] + NADP
Hydrogen ion + NADPH + 3 -Oxo-glutaryl-[acyl-carrier protein] methyl ester >3 -Hydroxyglutaryl-[acyl-carrier protein] methyl ester + NADP
Hydrogen ion + NADPH + 3 -Oxo-pimeloyl-[acyl-carrier protein] methyl ester >3 -Hydroxypimeloyl-[acyl-carrier protein] methyl ester + NADP
Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH
L-Glutamyl-tRNA(Glu) + Hydrogen ion + NADPH > (S)-4-Amino-5-oxopentanoate + NADP + tRNA (Glu)
But-2-enoyl-[acyl-carrier protein] + Hydrogen ion + NADPH > Butyryl-ACP (n-C4:0ACP) + NADP
Hydrogen ion + NADPH + trans-3-cis-11-vacceoyl-[acyl-carrier protein] > NADP + cis-octadec-11-enoyl-[acyl-carrier protein] (n-C18:1)
Hydrogen ion + NADPH + trans-3-cis-5-dodecenoyl-[acyl-carrier protein] > cis-dodec-5-enoyl-[acyl-carrier protein] (n-C12:1) + NADP
Hydrogen ion + NADPH + trans-3-cis-7-myristoleoyl-[acyl-carrier protein] > NADP + cis-tetradec-7-enoyl-[acyl-carrier protein] (n-C14:1)
Hydrogen ion + NADPH + trans-3-cis-9-palmitoleoyl-[acyl-carrier protein] > cis-hexadec-9-enoyl-[acyl-carrier protein] (n-C16:1) + NADP
Hydrogen ion + NADPH + trans-Dec-2-enoyl-[acyl-carrier protein] > Decanoyl-ACP (n-C10:0ACP) + NADP
Hydrogen ion + NADPH + trans-Dodec-2-enoyl-[acyl-carrier protein] > Dodecanoyl-ACP (n-C12:0ACP) + NADP
Hydrogen ion + NADPH + trans-Hex-2-enoyl-[acyl-carrier protein] > Hexanoyl-ACP (n-C6:0ACP) + NADP
Hydrogen ion + NADPH + trans-Hexadec-2-enoyl-[acyl-carrier protein] > NADP + Palmitoyl-ACP (n-C16:0ACP)
Hydrogen ion + NADPH + trans-Oct-2-enoyl-[acyl-carrier protein] > NADP + Octanoyl-ACP (n-C8:0ACP)
Hydrogen ion + NADPH + trans-octadec-2-enoyl-[acyl-carrier protein] > NADP + Octadecanoyl-ACP (n-C18:0ACP)
Hydrogen ion + NADPH + trans-Tetradec-2-enoyl-[acyl-carrier protein] > Myristoyl-ACP (n-C14:0ACP) + NADP
Enoylglutaryl-[acyl-carrier protein] methyl ester + Hydrogen ion + NADPH > Glutaryl-[acyl-carrier protein] methyl ester + NADP
Enoylpimeloyl-[acyl-carrier protein] methyl ester + Hydrogen ion + NADPH > NADP + Pimeloyl-[acyl-carrier protein] methyl ester
gamma-Glutamyl-gamma-butyraldehyde + Water + NADP <> 4-(Glutamylamino) butanoate +2 Hydrogen ion + NADPH
2-Oxepin-2(3H)-ylideneacetyl-CoA + 2 Water + NADP > 3-Oxo-5,6-dehydrosuberyl-CoA +2 Hydrogen ion + NADPH
NADP + L-Serine <> 2-Aminomalonate semialdehyde + Hydrogen ion + NADPH
NADP + D-Serine <> 2-Aminomalonate semialdehyde + Hydrogen ion + NADPH
L-Allothreonine + NADP <> L-2-Amino-3-oxobutanoic acid + Hydrogen ion + NADPH
7,8-Dihydroneopterin + Hydrogen ion + NADPH > NADP + Tetrahydromonapterin
L-Glutamate + Water + NADP <> alpha-Ketoglutarate + Hydrogen ion + NADPH + Ammonium
Glucose 6-phosphate + NADP <> 6-Phosphonoglucono-D-lactone + Hydrogen ion + NADPH
6-Phosphogluconic acid + NADP <> Carbon dioxide + NADPH + D-Ribulose 5-phosphate + Hydrogen ion
dTDP-4-Dehydro-6-deoxy-L-mannose + Hydrogen ion + NADPH <> Deoxythymidine diphosphate-L-rhamnose + NADP
GDP-4-Oxo-L-fucose + Hydrogen ion + NADPH > GDP-L-Fucose + NADP
L-Malic acid + NADP > Carbon dioxide + NADPH + Pyruvic acid
NADPH + 2 Nitric oxide + 2 Oxygen > Hydrogen ion + NADP +2 Nitrate
3 Hydrogen ion + 2 NADPH + 7-Cyano-7-carbaguanine >2 NADP + Queuine
2-Demethylmenaquinone 8 + Hydrogen ion + NADPH > 2-Demethylmenaquinol 8 + NADP
Hydrogen ion + NADPH + Ubiquinone-8 > NADP + Ubiquinol-8
Hydrogen ion + Menaquinone 8 + NADPH > Menaquinol 8 + NADP
L-Aspartate-semialdehyde + NADP + Phosphate <> L-Aspartyl-4-phosphate + Hydrogen ion + NADPH
D-Biotin D-sulfoxide + Hydrogen ion + NADPH > Biotin + Water + NADP
2 -Dehydro-L-gulonate + Hydrogen ion + NADPH > Gluconic acid + NADP
2 -Dehydro-L-gulonate + Hydrogen ion + NADPH > D-Galactonate + NADP
2,5-Diketo-D-gluconate + Hydrogen ion + NADPH > 5-Keto-D-gluconate + NADP
Water + NADP + Propanal >2 Hydrogen ion + NADPH + Propionic acid
Acetaldehyde + Water + NADP > Acetic acid +2 Hydrogen ion + NADPH
Glycerol 3-phosphate + NADP <> Dihydroxyacetone phosphate + Hydrogen ion + NADPH
2-Aceto-2-hydroxy-butyrate + Hydrogen ion + NADPH <> (R) 2,3-Dihydroxy-3-methylvalerate + NADP
(R)-2,3-Dihydroxy-isovalerate + NADP <> (S)-2-Acetolactate + Hydrogen ion + NADPH
N-Acetyl-L-glutamate 5-semialdehyde + NADP + Phosphate <> N-Acetyl-L-glutamyl 5-phosphate + Hydrogen ion + NADPH
Hydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine <> NADP + UDP-N-Acetylmuraminate
S-Adenosylmethionine + NADPH + L-Tyrosine > p-Cresol + 5'-Deoxyadenosine + Dehydroglycine + Hydrogen ion + L-Methionine + NADP
5-Keto-D-gluconate + Hydrogen ion + NADPH <> Gluconic acid + NADP
5-Keto-D-gluconate + Hydrogen ion + NADPH > D-Galactonate + NADP
2 L-Glutamate + NADP <> L-Glutamine + alpha-Ketoglutarate + NADPH + Hydrogen ion
2 Glutathione + NADP <> Glutathione disulfide + NADPH + Hydrogen ion
L-Malic acid + NADP <> Pyruvic acid + Carbon dioxide + NADPH + Hydrogen ion
L-Glutamate + NADP + Water <> alpha-Ketoglutarate + Ammonia + NADPH + Hydrogen ion
Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion
Glycolic acid + NADP <> Glyoxylic acid + NADPH + Hydrogen ion
L-D-1-Pyrroline-5-carboxylic acid + NADP + 2 Water <> L-Glutamate + NADPH + Hydrogen ion
Tetrahydrofolic acid + 2 NADP <> Folic acid +2 NADPH +2 Hydrogen ion
Inosinic acid + Ammonia + NADP <> Guanosine monophosphate + NADPH + Hydrogen ion
5,10-Methylene-THF + NADP <> 5,10-Methenyltetrahydrofolate + NADPH
5-Methyltetrahydrofolic acid + NADP <> 5,10-Methylene-THF + NADPH + Hydrogen ion
6-Phosphogluconic acid + NADP <> D-Ribulose 5-phosphate + Carbon dioxide + NADPH + Hydrogen ion
Gluconic acid + NADP <> 2-Keto-D-gluconic acid + NADPH + Hydrogen ion + 2-Dehydro-D-gluconate
Glyceric acid + NADP <> Tartronate semialdehyde + NADPH + Hydrogen ion
Isocitric acid + NADP <> Oxalosuccinic acid + NADPH + Hydrogen ion
(S)-3-Hydroxybutanoyl-CoA + NADP + 3-Hydroxybutyryl-CoA <> Acetoacetyl-CoA + NADPH + Hydrogen ion
Thioredoxin + NADP + Thioredoxin <> Thioredoxin disulfide + NADPH + Hydrogen ion + Thioredoxin disulfide
Dihydrofolic acid + NADP <> Folic acid + NADPH + Hydrogen ion
3-Dehydro-L-gulonate + NADP <> 2,3-Diketo-L-gulonate + NADPH + Hydrogen ion
beta-D-Glucose 6-phosphate + NADP <> 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen ion
(S)-Ureidoglycolic acid + NADP <> Oxalureate + NADPH + Hydrogen ion
2-Acetolactate + NADPH + Hydrogen ion <> 2,3-Dihydroxyisovaleric acid + NADP
Hydroxyproline + NADP <> Pyrroline hydroxycarboxylic acid + NADPH + Hydrogen ion
L-Glutamic-gamma-semialdehyde + Phosphate + NADP <> L-Glutamyl 5-phosphate + NADPH + Hydrogen ion + L-Glutamic acid 5-phosphate
Hydrogen selenide + 3 NADP + 3 Water <> Selenite +3 NADPH +5 Hydrogen ion
L-Glutamyl-tRNA(Glu) + NADPH + Hydrogen ion + tRNA(Glu) <> (S)-4-Amino-5-oxopentanoate + tRNA(Glu) + NADP + L-Glutamyl-tRNA(Glu)
(R)-2,3-Dihydroxy-isovalerate + NADP <> 3-Hydroxy-3-methyl-2-oxobutanoic acid + NADPH + Hydrogen ion
Pyrroline hydroxycarboxylic acid + NADP + 2 Water <> L-erythro-4-Hydroxyglutamate + NADPH + Hydrogen ion
(3R)-3-Hydroxybutanoyl-[acyl-carrier protein] + NADP <> Acetoacetyl-[acp] + NADPH + Hydrogen ion
(3R)-3-Hydroxydecanoyl-[acyl-carrier protein] + NADP <> 3-Oxodecanoyl-[acp] + NADPH
(3R)-3-Hydroxyoctanoyl-[acyl-carrier protein] + NADP <> 3-Oxooctanoyl-[acp] + NADPH + Hydrogen ion
(3R)-3-Hydroxypalmitoyl-[acyl-carrier protein] + NADP <> 3-Oxohexadecanoyl-[acp] + NADPH + Hydrogen ion
(3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + NADP <> 3-Oxotetradecanoyl-[acp] + NADPH + Hydrogen ion
(R)-3-Hydroxyhexanoyl-[acp] + NADP <> 3-Oxohexanoyl-[acp] + NADPH + Hydrogen ion
(R)-3-Hydroxydodecanoyl-[acp] + NADP <> 3-Oxododecanoyl-[acp] + NADPH + Hydrogen ion
2-Octaprenylphenol + Oxygen + NADPH + Hydrogen ion <> 2-Octaprenyl-6-hydroxyphenol + NADP + Water
(R) 2,3-Dihydroxy-3-methylvalerate + NADP <> (R)-3-Hydroxy-3-methyl-2-oxopentanoate + NADPH + Hydrogen ion
4-Chlorobiphenyl + Oxygen + NADPH + Hydrogen ion <> cis-2,3-Dihydro-2,3-dihydroxy-4'-chlorobiphenyl + NADP
Biphenyl + Oxygen + NADPH + Hydrogen ion <> cis-2,3-Dihydro-2,3-dihydroxybiphenyl + NADP
3-Hydroxybutanoyl-CoA + NADP <> Acetoacetyl-CoA + NADPH + Hydrogen ion
L-Idonate + NADP <> 5-Dehydro-D-gluconate + NADPH + Hydrogen ion
GDP-L-Fucose + NADP <> GDP-4-Dehydro-6-deoxy-D-mannose + NADPH + Hydrogen ion
1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion <> Isopentenyl pyrophosphate + NADP + Water
Quinate + NADP <> 3-Dehydroquinate + NADPH + Hydrogen ion
Dimethylallylpyrophosphate + NADP + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion
3-Oxooctadecanoyl-CoA + NADPH + Hydrogen ion <> 3-Hydroxyoctadecanoyl-CoA + NADP
3-Oxostearoyl-[acp] + NADPH + Hydrogen ion <> 3-Hydroxyoctadecanoyl-[acp] + NADP
Trinitrotoluene + 2 NADPH + 2 Hydrogen ion <> 4-Hydroxylamino-2,6-dinitrotoluene +2 NADP + Water
2-Polyprenylphenol + Oxygen + NADPH <> 2-Polyprenyl-6-hydroxyphenol + NADP + Water
2-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinone + Oxygen + NADPH + Hydrogen ion <> 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + NADP + Water
2 NADPH + 2 Hydrogen ion + Methylselenic acid <>2 NADP +2 Water + Methaneselenol
3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde + NADP + Water <> 3-Oxo-5,6-dehydrosuberyl-CoA + NADPH + Hydrogen ion
Phenylacetyl-CoA + Oxygen + NADPH + Hydrogen ion <> 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + Water + NADP + 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA
Hydrogen ion + L-Glutamate + Adenosine triphosphate + NADPH > ADP + L-Glutamic-gamma-semialdehyde + NADP + Phosphate
curcumin + NADPH + Hydrogen ion > dihydrocurcumin + NADP
dihydrocurcumin + NADPH + Hydrogen ion > tetrahydrocurcumin + NADP
NADP + Gluconic acid <> Hydrogen ion + 2-Dehydro-D-gluconate + NADPH
Hydrogen ion + NADPH + 2,5-Diketo-D-gluconate <> 2-Dehydro-D-gluconate + NADP
2-Octaprenyl-6-methoxyphenol + Oxygen + NADPH + Hydrogen ion > 2-Octaprenyl-6-methoxy-1,4-benzoquinol + Water + NADP
acetoin + NADP diacetyl + NADPH + Hydrogen ion
(R)-2,3-Dihydroxy-isovalerate + NADP <> (<i>S</i>)-2-acetolactate + NADPH + Hydrogen ion
NADP + an alcohol an aldehyde + NADPH + Hydrogen ion
an aldehyde + Water + NADP a carboxylate + NADPH + Hydrogen ion
(2E)-Decenoyl-CoA + NADP <> Hydrogen ion + trans-Delta2, cis-delta4-decadienoyl-CoA + NADPH
NADP + Deoxythymidine diphosphate-L-rhamnose <> Hydrogen ion + NADPH + dTDP-4-dehydro-6-deoxy-&beta;-L-mannose
L-Glutamate + NADP < Hydrogen ion + L-Glutamine + Oxoglutaric acid + NADPH
L-Glutamate + Water + NADP <> Hydrogen ion + Oxoglutaric acid + Ammonia + NADPH
Isocitric acid + NADP > NADPH + Oxoglutaric acid + Carbon dioxide
NADPH + a quinone <> NADP + a semiquinone
an oxidized nitroaromatic compound + NADPH <> a reduced nitroaromatic compound + NADP
(<i>S</i>)-NADPHX + ADP NADPH + Adenosine monophosphate + Phosphate + Hydrogen ion
Lactaldehyde + NADP < Pyruvaldehyde + NADPH + Hydrogen ion
Hydrogen ion + Ethyl-2-methylacetoacetate + NADPH <> Ethyl-(2R)-methyl-(3S)-hydroxybutanoate + NADP
Phenylacetyl-CoA + Oxygen + NADPH + Hydrogen ion > 2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP + Water
NADPH + Hydrogen ion + an electron-transfer-related quinone > NADP + an electron-transfer-related quinol
preQ<sub>1</sub> + NADP < 7-Cyano-7-carbaguanine + NADPH + Hydrogen ion
Glycerol 3-phosphate + NADP < Hydrogen ion + L-Glyceraldehyde 3-phosphate + NADPH
3-hydroxypropionaldehyde + NADPH + Hydrogen ion 1,3-propanediol + NADP
Iron + a siderophore + NADP < an Fe(III)-siderophore + NADPH + Hydrogen ion
Iron + (2,3-dihydroxybenzoylserine)<sub>3</sub> + NADP < ferric 2,3-dihydroxybenzoylserine + NADPH + Hydrogen ion
a 2,3,4-saturated fatty acyl CoA + NADP > a <i>trans</i>-2-enoyl-CoA + NADPH + Hydrogen ion
Hydrogen ion + 2-Dehydro-D-gluconate + NADPH <> L-Idonate + NADP
6-Phosphogluconic acid + NADP > D-Ribulose 5-phosphate + Carbon dioxide + NADPH
N-Acetyl-L-glutamate 5-semialdehyde + NADP + Inorganic phosphate > N-Acetyl-L-glutamyl 5-phosphate + NADPH
Tetrahydrocurcumin + 2 NADP > curcumin +2 NADPH
Hydrogen sulfide + 3 NADP + 3 Water > Sulfite +3 NADPH
L-Glutamate + Water + NADP > Oxoglutaric acid + Ammonia + NADPH
Tetrahydrofolic acid + NADP > Dihydrofolic acid + NADPH
(3R)-3-hydroxyacyl-[acyl-carrier-protein] + NADP > 3-oxoacyl-[acyl-carrier-protein] + NADPH
Trans-2,3-didehydroacyl-CoA + NADP > trans,trans-2,3,4,5-tetradehydroacyl-CoA + NADPH
GDP-L-Fucose + NADP > GDP-4-Dehydro-6-deoxy-D-mannose + NADPH
2 reduced ferredoxin + NADP + Hydrogen ion >2 oxidized ferredoxin + NADPH
Glucose 6-phosphate + NADP > 6-Phosphonoglucono-D-lactone + NADPH
Succinic acid semialdehyde + NADP + Water > Succinic acid + NADPH
Glycolic acid + NADP > Glyoxylic acid + NADPH
Gluconic acid + NADP > 2-Dehydro-D-gluconate + NADPH
2 L-Glutamate + NADP > L-Glutamine + Oxoglutaric acid + NADPH
2 Glutathione + NADP > Glutathione disulfide + NADPH
Inosinic acid + Ammonia + NADP > Guanosine monophosphate + NADPH
(S)-4-Amino-5-oxopentanoate + NADP + tRNA(Glu) > L-glutamyl-tRNA(Glu) + NADPH
(R)-2,3-Dihydroxy-isovalerate + NADP > (S)-2-Acetolactate + NADPH
(R) 2,3-Dihydroxy-3-methylvalerate + NADP > 2-Aceto-2-hydroxy-butyrate + NADPH
UDP-N-Acetylmuraminate + NADP > UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADPH
Phenylacetyl-CoA + NADPH + Oxygen > 2-(1,2-Epoxy-1,2-dihydrophenyl)acetyl-CoA + NADP + Water
3-Hydroxybutyryl-CoA + NADP > Acetoacetyl-CoA + NADPH
3-Oxo-5,6-dehydrosuberyl-CoA semialdehyde + NADP + Water > 3-Oxo-5,6-dehydrosuberyl-CoA + NADPH
(R)-Pantoate + NADP > 2-Dehydropantoate + NADPH
L-Glutamic-gamma-semialdehyde + Inorganic phosphate + NADP > L-Glutamic acid 5-phosphate + NADPH
NADPH + 2 Quinone > NADP +2 semiquinone
7-Aminomethyl-7-carbaguanine + 2 NADP > 7-Cyano-7-carbaguanine +2 NADPH
5-Amino-6-(5'-phosphoribitylamino)uracil + NADP > 5-amino-6-(5-phospho-D-ribosylamino)uracil + NADPH
3-Hydroxypropanoate + NADP > Malonic semialdehyde + NADPH
FMNH(2) + NADP > Flavin Mononucleotide + NADPH
Thioredoxin + NADP > thioredoxin disulfide + NADPH
An alcohol + NADP > Aldehyde + NADPH
2 Iron + 2 an apo-siderophore + NADP + Hydrogen ion >2 an Fe(III)-siderophore + NADPH
Tetrahydropteridine + NADP > 6,7-Dihydropteridine + NADPH
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
NADP <> 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion
L-Allothreonine + NADP + L-2-Amino-3-oxobutanoic acid <> Aminoacetone + Carbon dioxide + NADPH + Hydrogen ion
Quinate + NAD + NADP + Shikimic acid <> 3-Dehydroquinate + NADH + NADPH + Hydrogen ion + 3-Dehydro-shikimate
Nitric oxide + 2 Oxygen + NADH + NADPH <>2 Nitrate + NAD + NADP + Hydrogen ion
7-Aminomethyl-7-carbaguanine + NADP <> 7-Cyano-7-carbaguanine + NADPH +2 Hydrogen ion
trans-2,3-Dehydroacyl-CoA + NADP <> trans,trans-2,3,4,5-Tetradehydroacyl-CoA + NADPH + Hydrogen ion
2 L-Glutamate + NADP + Ammonia + Water <> L-Glutamine + alpha-Ketoglutarate + NADPH + Hydrogen ion
3-Dehydro-L-gulonate + NAD + NADP <> 2,3-Diketo-L-gulonate + NADH + NADPH + Hydrogen ion
5-Methyltetrahydrofolic acid + NAD + NADP <> 5,10-Methylene-THF + NADH + NADPH + Hydrogen ion
ADP + (6S)-6-beta-hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide + (6S)-6beta-Hydroxy-1,4,5,6-tetrahydronicotinamide-adenine dinucleotide phosphate <> Adenosine monophosphate + Phosphate + NADH + NADPH
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
L-Malic acid + NADP + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADPH
NADP + Hydrogen ion <> NADPH
Glycerol 3-phosphate + NAD + NADP <> Dihydroxyacetone phosphate + NADH + NADPH + Hydrogen ion
Reduced ferredoxin + NADP + Hydrogen ion <> Oxidized ferredoxin + NADPH
L-Tyrosine + S-Adenosylmethionine + NADPH <> 2-iminoacetate + p-Cresol + 5'-Deoxyadenosine + L-Methionine + NADP + Hydrogen ion
NADPH + Hydrogen ion + 2 Quinone <> NADP +2 Semiquinone
Gluconic acid + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ion
L-Idonate + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ion
Alcohol + NADP <> Aldehyde + NADPH + Hydrogen ion
Propionyl-CoA + NADP <> Acrylyl-CoA + NADPH + Hydrogen ion
Isocitric acid + NADP + Oxalosuccinic acid <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion
Ammonia + NAD + 3 NADP + 2 Water <> Nitrite + NADH +3 NADPH +5 Hydrogen ion
(3R)-3-Hydroxyacyl-[acyl-carrier protein] + NADP <> 3-Oxoacyl-[acyl-carrier protein] + NADPH + Hydrogen ion
(S)-Ureidoglycolic acid + NAD + NADP <> Oxalureate + NADH + NADPH + Hydrogen ion
beta-D-Glucose 6-phosphate + NADP > 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen ion + NADPH
6-Phosphogluconic acid + NADP > D-Ribulose 5-phosphate + Carbon dioxide + NADPH + NADPH
Hydrogen ion + NADPH + Ammonia + NADPH <> Water + NADP + L-Glutamic acid + L-Glutamate
Oxoglutaric acid + NADPH + Ammonium + Hydrogen ion + NADPH > L-Glutamic acid + Water + NADP + L-Glutamate
2 L-Glutamic acid + NADP + 2 L-Glutamate > L-Glutamine + NADPH + Hydrogen ion + Oxoglutaric acid + NADPH
3-Ketoglutaryl-[acp] methyl ester + NADPH + Hydrogen ion + NADPH > NADP + a 3R-hydroxyglutaryl-[acp] methyl ester
3-Ketopimeloyl-[acp] methyl ester + NADPH + Hydrogen ion + NADPH > NADP + 3-Hydroxypimeloyl-[acp] methyl ester
3-oxo-cis-?5-dodecenoyl-[acp]? + Hydrogen ion + NADPH + NADPH > 3R-hydroxy cis ?9-hexadecenoyl-[acp] + NADP
a 3-oxo-cis-?7-tetradecenoyl-[acp]? + Hydrogen ion + NADPH + NADPH > a 3R-hydroxy cis ?7-tetradecenoyl-[acp] + NADP
3-oxo-cis-?9-hexadecenoyl-[acp]? + Hydrogen ion + NADPH + NADPH > NADP + 3R-hydroxy cis ?9-hexadecenoyl-[acp]
3-oxo-cis-vaccenoyl-[acp]? + Hydrogen ion + NADPH + NADPH > NADP + (R)-3-hydroxy-cis-vaccenoyl-[acp]
3-oxoacyl-[acp]? + Hydrogen ion + NADPH + NADPH > NADP + (3R)-3-hydroxyacyl-[acyl-carrier protein]
acetoacetyl-[acp] + Hydrogen ion + NADPH + NADPH > NADP + (R)-3-hydroxybutanoyl-[acp]
3-oxo-hexanoyl-[acp]? + Hydrogen ion + NADPH + NADPH > (R)-3-hydroxyhexanoyl-[acp] + NADP
3-oxo-octanoyl-[acp]? + Hydrogen ion + NADPH + NADPH > NADP + (R)-3-hydroxyoctanoyl-[acp]
3-oxo-decanoyl-[acp]? + Hydrogen ion + NADPH + NADPH > NADP + an (R)-3-hydroxydecanoyl-[acp]?
3-oxo-dodecanoyl-[acp]? + Hydrogen ion + NADPH + NADPH > NADP + (R)-3-hydroxydodecanoyl-[acp]
3-oxo-myristoyl-[acp]? + Hydrogen ion + NADPH + NADPH > NADP + (3R)-3-hydroxymyristoyl-[acp]
3-oxo-palmitoyl-[acp]? + Hydrogen ion + NADPH + NADPH > NADP + (R)-3-hydroxypalmitoyl-[acp]
3-oxo-cis-?5-dodecenoyl-[acp]? + Hydrogen ion + NADPH + NADPH > NADP + a (3R)-hydroxy cis ?5-dodecenoyl-[acp]
Glutaryl-[acp] methyl ester + NADP < NADPH + Hydrogen ion + Enoylglutaryl-[acp] methyl ester + NADPH
NADPH + Hydrogen ion + an enoylpimeloyl-[acp] methyl ester + NADPH > NADP + a pimeloyl-[acp] methyl ester
trans-2-enoyl-[acyl-carrier protein] + Hydrogen ion + NADPH + NADPH > NADP + 2,3,4-saturated fatty acyl-[acp]
L-Aspartyl-4-phosphate + NADPH + Hydrogen ion + NADPH > Phosphate + NADP + L-Aspartate-semialdehyde
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + Hydrogen ion + NADPH + (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + NADPH > Water + NADP + (S)-2,3,4,5-tetrahydrodipicolinate
Dihydrofolic acid + NADP + Dihydrofolic acid > Folic acid + NADPH + Hydrogen ion + NADPH
Dihydrofolic acid + NADPH + Hydrogen ion + Dihydrofolic acid + NADPH > Tetrahydrofolic acid + NADP + Tetrahydrofolic acid
7,8-dihydrofolate monoglutamate + Hydrogen ion + NADPH + Dihydrofolic acid + NADPH > NADP + Tetrahydrofolic acid + Tetrahydrofolic acid
Folic acid + 2 NADPH + 2 Hydrogen ion + 2 NADPH > Tetrahydrofolic acid +2 NADP + Tetrahydrofolic acid
5,10-Methylene-THF + NADPH + Hydrogen ion + 5,10-Methylene-THF + NADPH > 5-Methyltetrahydrofolic acid + NADP + 5-Methyltetrahydrofolic acid
5,10-Methenyltetrahydrofolic acid + NADPH + NADPH > 5,10-Methylene-THF + NADP + 5,10-Methylene-THF
D-threo-Isocitric acid + NADP > Carbon dioxide + NADPH + Oxoglutaric acid + NADPH
N-Acetyl-L-glutamyl 5-phosphate + NADPH + Hydrogen ion + NADPH > N-acetyl-L-glutamate + Phosphate + NADP
4-(γ-glutamylamino)butanal + Water + NADP > 4-(Glutamylamino) butanoate +2 Hydrogen ion + NADPH + NADPH
Succinic acid semialdehyde + Water + NADP > NADPH +2 Hydrogen ion + Succinic acid + NADPH
L-Glutamic acid 5-phosphate + Hydrogen ion + NADPH + NADPH > L-Glutamic-gamma-semialdehyde + NADP + Phosphate
1-Pyrroline-5-carboxylic acid + Hydrogen ion + NADPH + L-D-1-Pyrroline-5-carboxylic acid + NADPH > NADP + L-Proline + L-Proline
Tartronate semialdehyde + Hydrogen ion + NADPH + NADPH > NADP + Glyceric acid
3 NADPH + 5 Hydrogen ion + Sulfite + 3 NADPH + Sulfite > Hydrogen sulfide +3 Water +3 NADP
Sulfide + Water + 3 NADP > Sulfite +3 NADPH + Sulfite +3 NADPH
(R)-2,3-Dihydroxy-isovalerate + Hydrogen ion + NADPH + NADPH > NADP + (R) 2,3-Dihydroxy-3-methylvalerate
2-Aceto-2-hydroxy-butyrate + NADPH + Hydrogen ion + NADPH > NADP + (R) 2,3-Dihydroxy-3-methylvalerate
2-dehydropantoate + NADPH + Hydrogen ion + 2-Dehydropantoate + NADPH > NADP + (R)-pantoate + (R)-Pantoate
(S)-2-Acetolactate + Hydrogen ion + NADPH + NADPH > NADP + (R)-2,3-Dihydroxy-isovalerate
3-dehydroshikimate + Hydrogen ion + NADPH + 3-Dehydro-shikimate + NADPH > NADP + Shikimic acid
L-Aspartate-semialdehyde + Hydrogen ion + NADPH + NADPH > NADP + L-Homoserine + L-Homoserine
L-Malic acid + NADP + L-Malic acid > Carbon dioxide + NADPH + Pyruvic acid + NADPH
GDP-4-Dehydro-6-deoxy-D-mannose + NADPH + Hydrogen ion + NADPH > GDP-L-Fucose + NADP
GDP-4-dehydro-6-deoxy-α-D-mannose + NADPH + Hydrogen ion + NADPH > NADP + GDP-β-L-fucose
Oxidized glutathione + Hydrogen ion + NADPH + Glutathione disulfide + NADPH > NADP +2 Glutathione
Dihydroxyacetone phosphate + Hydrogen ion + NADPH + NADPH > NADP + Glycerol 3-phosphate
UDP-N-acetyl-α-D-glucosamine-enolpyruvate + NADPH + Hydrogen ion + NADPH > NADP + UDP-N-acetyl-α-D-muramate
8 L-glutamyl-tRNA(Glu) + 8 NADPH + 8 NADPH >8 tRNA(Glu) +8 NADP +8 (S)-4-Amino-5-oxopentanoate
NADPH + Hydrogen ion + 1-Deoxy-D-xylulose 5-phosphate + NADPH + 1-Deoxy-D-xylulose 5-phosphate > NADP + 2-C-methyl-D-erythritol 4-phosphate
1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + Hydrogen ion + NADPH + NADPH > Water + NADPH + Isopentenyl pyrophosphate + Isopentenyl pyrophosphate
1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + Hydrogen ion + NADPH + NADPH > NADP + Water + Dimethylallylpyrophosphate + Dimethylallylpyrophosphate
2-Octaprenylphenol + Hydrogen ion + NADPH + Oxygen + NADPH > NADP + Water + 2-Octaprenyl-6-hydroxyphenol + 2-Octaprenyl-6-hydroxyphenol
Hydrogen ion + NADPH + Oxygen + 2-methoxy-6-(all-trans-octaprenyl)phenol + NADPH > Water + NADP + 2-Octaprenyl-6-methoxy-1,4-benzoquinol
L-Tyrosine + NADPH + S-adenosyl-L-methionine + L-Tyrosine + NADPH > Hydrogen ion + NADP + L-Methionine + 5'-Deoxyadenosine + p-Cresol + 2-iminoacetate
7-Cyano-7-carbaguanine + 3 Hydrogen ion + 2 NADPH + 2 NADPH >2 NADP + 7-Aminomethyl-7-carbaguanine
7-Cyano-7-carbaguanine + 3 Hydrogen ion + 2 NADPH + 2 NADPH > Queuine +2 NADP + Queuine
Curcumin + Hydrogen ion + NADPH + curcumin + NADPH > NADP + Dihydrocurcumin + Dihydrocurcumin
Dihydrocurcumin + Hydrogen ion + NADPH + Dihydrocurcumin + NADPH > Tetrahydrocurcumin + NADP
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0921103300-a94dc77e4683c53f1e1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-5fcc7bc2ff00254e837aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0920000000-91a94a0d16f7db6907e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0036-6900111800-7f73a4ecf431645a13cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3901000000-b9bf964190caf0afebdeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900000000-f6e201cd60ed9314f31aView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference: Seelbach, Karsten; Riebel, Bettina; Hummel, Werner; Kula, Maria-Regina; Tishkov, Vladimir I.; Egorov, Alexey M.; Wandrey, Christian; Kragl, Udo. A novel, efficient regenerating method of NADPH using a new formate dehydrogenase. Tetrahedron Letters (1
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID16474
HMDB IDHMDB00221
Pubchem Compound ID5884
Kegg IDC00005
ChemSpider ID17215925
WikipediaNADPH
BioCyc IDNADPH
EcoCyc IDNADPH
Ligand ExpoNDP