P. aeruginosa Metabolome Database: NADH (PAMDB110540)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB110540

Identification

Name:

NADH

Description:

Dianion of NADH arising from deprotonation of the two diphosphate OH groups; major species at pH 7.3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

NADH₂
NADH2
dihydrodiphosphopyridine nucleotide
diphosphopyridine nucleotide reduced
dihydronicotinamide adenine dinucleotide
nicotinamide adenine dinucleotide reduced
NAD-reduced
NADH+H+
DPNH
β-NADH

Chemical Formula:

C₂₁H₂₇N₇O₁₄P₂

Average Molecular Weight:

663.43

Monoisotopic Molecular Weight:

665.1247716967

InChI Key:

BOPGDPNILDQYTO-NNYOXOHSSA-L

InChI:

InChI=1S/C21H29N7O14P2/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/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/p-2/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

CAS number:

58-68-4

IUPAC Name:

adenosine 5'-{3-[1-(3-carbamoyl-1,4-dihydropyridin-1-yl)-1,4-anhydro-D-ribitol-5-yl] diphosphate}

Traditional IUPAC Name:

NADH

SMILES:

C1(=C(CC=CN1C5(OC(COP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N4(C=NC3(C(N)=NC=NC=34))))C(O)C(O)5))C(N)=O)

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of chemical entities known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Nucleosides, nucleotides, and analogues

Sub Class

(5'->5')-dinucleotides

Direct Parent

(5'->5')-dinucleotides

Alternative Parents

Substituents

(5'->5')-dinucleotide
Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Nicotinamide-nucleotide
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
N-substituted nicotinamide
Organic pyrophosphate
6-aminopurine
Imidazopyrimidine
Purine
Monoalkyl phosphate
Dihydropyridine
Aminopyrimidine
N-substituted imidazole
Imidolactam
Organic phosphoric acid derivative
Pyrimidine
Hydropyridine
Alkyl phosphate
Monosaccharide
Phosphoric acid ester
Primary aromatic amine
Oxolane
Imidazole
Vinylogous amide
Azole
Heteroaromatic compound
Amino acid or derivatives
Secondary alcohol
Carboxamide group
Primary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Enamine
Hydrocarbon derivative
Organopnictogen compound
Amine
Primary amine
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

NAD (CHEBI:16908 )
NAD(P)H (CHEBI:16908 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

140.0 - 142.0 °C

Experimental Properties:

Property	Value	Reference
Melting Point	140.0 - 142.0 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.95 mg/mL	ALOGPS
logP	-1.4	ALOGPS
logP	-6.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	-7	ChemAxon
pKa (Strongest Basic)	5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	317.62 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	143 m³·mol^-1	ChemAxon
Polarizability	57.65 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

More...

Pathways:

Ammonia Recycling pae00910
Androgen and Estrogen Metabolism pae00150
Arginine and Proline Metabolism pae00330
Beta-Alanine Metabolism pae00410
Betaine Metabolism pae00260
Bile Acid Biosynthesis pae00120
Butyrate Metabolism pae00650
Caffeine Metabolism pae00232
Citric Acid Cycle pae00020
Cysteine Metabolism pae00270
Fatty Acid Elongation In Mitochondria pae00062
Fatty acid Metabolism pae00071
Folate Metabolism pae00670
Fructose and Mannose Degradation pae00051
Galactose Metabolism pae00052
Gluconeogenesis pae00010
Glutamate Metabolism pae00250
Glycerolipid Metabolism pae00561
Glycine and Serine Metabolism pae00260
Glycolysis pae00010
Histidine Metabolism pae00340
Ketone Body Metabolism pae00072
Lysine Degradation pae00310
Methionine Metabolism pae00270
Mitochondrial Electron Transport Chain pae00190
Nicotinate and Nicotinamide Metabolism pae00760
Nucleotide Sugars Metabolism pae00520
Phospholipid Biosynthesis pae00564
Porphyrin Metabolism pae00860
Propanoate Metabolism pae00640
Pterine Biosynthesis pae00790
Purine Metabolism pae00230
Pyruvate Metabolism pae00620
Retinol Metabolism pae00830
Starch and Sucrose Metabolism pae00500
Steroidogenesis pae00140
Tryptophan Metabolism pae00380
Tyrosine Metabolism pae00350
Urea Cycle pae00330
Valine, Leucine and Isoleucine Degradation pae00280

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0931104000-bf6579d19ee9bc297e13	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0901000000-92672b1d4b96838f8652	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-ef56d203da65089e145f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03e9-1900207000-f248eb28a7283de7118b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1900100000-efadf1d6c54e9e86671d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a7i-3900000000-f258fc2bf1d8e54ac6da	View in MoNA

References

References:

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. [12130503 ]
Yamamoto T, Moriwaki Y, Takahashi S, Suda M, Higashino K: Ethanol as a xanthine dehydrogenase inhibitor. Metabolism. 1995 Jun;44(6):779-85. [7783663 ]
Nadlinger K, Westerthaler W, Storga-Tomic D, Birkmayer JG: Extracellular metabolisation of NADH by blood cells correlates with intracellular ATP levels. Biochim Biophys Acta. 2002 Nov 14;1573(2):177-82. [12399028 ]
Saada A, Bar-Meir M, Belaiche C, Miller C, Elpeleg O: Evaluation of enzymatic assays and compounds affecting ATP production in mitochondrial respiratory chain complex I deficiency. Anal Biochem. 2004 Dec 1;335(1):66-72. [15519572 ]
Heiman-Patterson TD, Argov Z, Chavin JM, Kalman B, Alder H, DiMauro S, Bank W, Tahmoush AJ: Biochemical and genetic studies in a family with mitochondrial myopathy. Muscle Nerve. 1997 Oct;20(10):1219-24. [9324076 ]
Mintun MA, Vlassenko AG, Rundle MM, Raichle ME: Increased lactate/pyruvate ratio augments blood flow in physiologically activated human brain. Proc Natl Acad Sci U S A. 2004 Jan 13;101(2):659-64. Epub 2004 Jan 2. [14704276 ]
Yeo SF, Zhang Y, Schafer D, Campbell S, Wong B: A rapid, automated enzymatic fluorometric assay for determination of D-arabinitol in serum. J Clin Microbiol. 2000 Apr;38(4):1439-43. [10747122 ]
Uppal A, Ghosh N, Datta A, Gupta PK: Fluorimetric estimation of the concentration of NADH from human blood samples. Biotechnol Appl Biochem. 2005 Feb;41(Pt 1):43-7. [15035655 ]
Yamamoto T, Moriwaki Y, Takahashi S, Suda M, Higashino K: Xylitol-induced increase in the concentration of oxypurines and its mechanism. Int J Clin Pharmacol Ther. 1995 Jun;33(6):360-5. [7582389 ]
Helge JW, Fraser AM, Kriketos AD, Jenkins AB, Calvert GD, Ayre KJ, Storlien LH: Interrelationships between muscle fibre type, substrate oxidation and body fat. Int J Obes Relat Metab Disord. 1999 Sep;23(9):986-91. [10490806 ]
Fulco M, Schiltz RL, Iezzi S, King MT, Zhao P, Kashiwaya Y, Hoffman E, Veech RL, Sartorelli V: Sir2 regulates skeletal muscle differentiation as a potential sensor of the redox state. Mol Cell. 2003 Jul;12(1):51-62. [12887892 ]
Li D, Gan Y, Wientjes MG, Badalament RA, Au JL: Distribution of DT-diaphorase and reduced nicotinamide adenine dinucleotide phosphate: cytochrome p450 oxidoreductase in bladder tissues and tumors. J Urol. 2001 Dec;166(6):2500-5. [11696818 ]
Desir G, Bratusch-Marrain P, DeFronzo RA: Effect of hyperketonemia on renal ammonia excretion in man. Metabolism. 1986 Aug;35(8):736-43. [3736414 ]
Odland LM, Heigenhauser GJ, Spriet LL: Effects of high fat provision on muscle PDH activation and malonyl-CoA content in moderate exercise. J Appl Physiol. 2000 Dec;89(6):2352-8. [11090589 ]
Rani K, Garg P, Pundir CS: Measurement of bile acid in serum and bile with arylamine-glass-bound 3alpha-hydroxysteroid dehydrogenase and diaphorase. Anal Biochem. 2004 Sep 1;332(1):32-7. [15301946 ]
Nomura H, Koike F, Tsuruta Y, Iwaki A, Iwaki T: Autopsy case of autosomal recessive hereditary spastic paraplegia with reference to the muscular pathology. Neuropathology. 2001 Sep;21(3):212-7. [11666018 ]
Orallo F, Alvarez E, Camina M, Leiro JM, Gomez E, Fernandez P: The possible implication of trans-Resveratrol in the cardioprotective effects of long-term moderate wine consumption. Mol Pharmacol. 2002 Feb;61(2):294-302. [11809853 ]
Jawed S, Stevens CR, Harrison R, Blake DR: Elevated circulating plasma NADH oxidising activity of xanthine oxidoreductase in plasma. Biochem Soc Trans. 1997 Aug;25(3):531S. [9388747 ]
Harbord MG, Hwang PA, Robinson BH, Becker LE, Hunjan A, Murphy EG: Infant-onset progressive myoclonus epilepsy. J Child Neurol. 1991 Apr;6(2):134-42. [1904460 ]
Mayevsky A, Meilin S, Manor T, Ornstein E, Zarchin N, Sonn J: Multiparametric monitoring of brain oxygen balance under experimental and clinical conditions. Neurol Res. 1998;20 Suppl 1:S76-80. [9584930 ]
Biellmann JF, Lapinte C, Haid E, Weimann G: Structure of lactate dehydrogenase inhibitor generated from coenzyme. Biochemistry. 1979 Apr 3;18(7):1212-7. [218616 ]
Lin SJ, Guarente L: Nicotinamide adenine dinucleotide, a metabolic regulator of transcription, longevity and disease. Curr Opin Cell Biol. 2003 Apr;15(2):241-6. [12648681 ]
Belenky P, Bogan KL, Brenner C: NAD+ metabolism in health and disease. Trends Biochem Sci. 2007 Jan;32(1):12-9. Epub 2006 Dec 11. [17161604 ]
Pollak N, Dolle C, Ziegler M: The power to reduce: pyridine nucleotides--small molecules with a multitude of functions. Biochem J. 2007 Mar 1;402(2):205-18. [17295611 ]
Khan JA, Forouhar F, Tao X, Tong L: Nicotinamide adenine dinucleotide metabolism as an attractive target for drug discovery. Expert Opin Ther Targets. 2007 May;11(5):695-705. [17465726 ]
WholeHealthMD [Link]

Synthesis Reference:

Marek, Miroslav; Vrbova, Eva; Horakova, Irena; Musil, Petr; Kefurt, Karel. NADH manufacture with immobilized Candida formate dehydrogenase. Czech. (1992), 4 pp.

Material Safety Data Sheet (MSDS)

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Links

External Links:

Resource	Link
CAS	58-68-4
ChEBI	57945
ChemSpider	10239197
HMDB	HMDB01487
IAF1260	33484
KEGG	C00004
MetaboLights	MTBLC57945
PubChem	21604869

NADH (PAMDB110540)

Structure for NADH (PAMDB110540)