NADH (CHEM035239)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:36:02 UTC
Update Date2016-11-09 01:21:16 UTC
Accession NumberCHEM035239
Identification
Common NameNADH
ClassSmall Molecule
DescriptionNADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, 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 . It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage. (Dorland, 27th ed)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,4-DIHYDRONICOTINAMIDE adenine dinucleotideChEBI
DPNHChEBI
Nicotinamide adenine dinucleotide (reduced)ChEBI
Reduced nicotinamide adenine dinucleotideChEBI
b-DPNHHMDB
b-NADHHMDB
beta-DPNHHMDB
beta-NADHHMDB
Dihydrocodehydrogenase IHMDB
DihydrocozymaseHMDB
Dihydronicotinamide adenine dinucleotideHMDB
Dihydronicotinamide mononucleotideHMDB
ENADAHMDB
NADH2HMDB
Reduced codehydrogenase IHMDB
Reduced diphosphopyridine nucleotideHMDB
Reduced nicotinamide adenine diphosphateHMDB
Reduced nicotinamide-adenine dinucleotideHMDB
NadideHMDB
Coenzyme IHMDB
DPNHMDB
Diphosphopyridine nucleotideHMDB
Nicotinamide adenine dinucleotideHMDB
Nicotinamide-adenine dinucleotideHMDB
NADHMDB
Nucleotide, diphosphopyridineHMDB
Adenine dinucleotide, dihydronicotinamideHMDB
Dinucleotide, dihydronicotinamide adenineHMDB
Dinucleotide, nicotinamide-adenineHMDB
Chemical FormulaC21H29N7O14P2
Average Molecular Mass665.441 g/mol
Monoisotopic Mass665.125 g/mol
CAS Registry Number58-68-4
IUPAC Name[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
Traditional NameNADH
SMILESNC1=C2N=CN(C3OC(COP(O)(=O)OP(O)(=O)OCC4OC(C(O)C4O)N4C=CCC(=C4)C(O)=N)C(O)C3O)C2=NC=N1
InChI IdentifierInChI=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)
InChI KeyBOPGDPNILDQYTO-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic 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
  • Purine ribonucleoside monophosphate
  • Nicotinamide-nucleotide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • N-substituted nicotinamide
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Dihydropyridine
  • Aminopyrimidine
  • Pyrimidine
  • Imidolactam
  • Monosaccharide
  • N-substituted imidazole
  • Alkyl phosphate
  • Phosphoric acid ester
  • Hydropyridine
  • Organic phosphoric acid derivative
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Imidazole
  • Vinylogous amide
  • Azole
  • Amino acid or derivatives
  • Primary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Organoheterocyclic compound
  • Enamine
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary amine
  • Amine
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.95 g/LALOGPS
logP-1.4ALOGPS
logP-5.9ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area317.62 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity143 m³·mol⁻¹ChemAxon
Polarizability57.65 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-1301902000-1a1639ad87019605438cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00n0-0210192000-bf07b6b154c5778067ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0150291000-84ef746651797f0679a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-0970000000-0688003193d7fc461235Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 35V, negativesplash10-00di-0190000000-775fe0fdd09a45ed6a96Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 35V, negativesplash10-052b-0019600000-3247f3ea96ec22c0e190Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 35V, negativesplash10-052b-0019600000-c62f2c56a1ce8a2874fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, negativesplash10-03di-3212549000-5bb7a136d3e7ca7d8eddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, negativesplash10-00ea-1219600000-1e722b38e19c9839c336Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00ea-1219600000-25943c109cf639eb967cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-05dj-5449401000-5b1b9b660a66672f95afSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000009000-c3a8f40f5761a0b33639Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-054k-6339301000-c1dfbc12dc893f53f0a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000009000-ced4da70fe9076bb4c29Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-05dj-5449401000-1c9466169a2e22067bd9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0000009000-f46730c3cbc0e239c819Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1329230000-4e5a5ac7f7ccdfcf5798Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00ea-1219600000-1e722b38e19c9839c336Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0002049000-452a7a02c7cdd0a7db02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0931104000-bf6579d19ee9bc297e13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-92672b1d4b96838f8652Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-ef56d203da65089e145fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03e9-1900207000-f248eb28a7283de7118bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900100000-efadf1d6c54e9e86671dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-3900000000-f258fc2bf1d8e54ac6daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000009000-7483a50cefc91ed6c523Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00157
HMDB IDHMDB0001487
FooDB IDFDB022649
Phenol Explorer IDNot Available
KNApSAcK IDC00019343
BiGG ID33484
BioCyc IDNADH
METLIN ID3687
PDB IDNot Available
Wikipedia LinkNicotinamide_adenine_dinucleotide
Chemspider ID903
ChEBI ID16908
PubChem Compound ID439153
Kegg Compound IDC00004
YMDB IDYMDB00143
ECMDB IDECMDB01487
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Marek, Miroslav; Vrbova, Eva; Horakova, Irena; Musil, Petr; Kefurt, Karel. NADH manufacture with immobilized Candida formate dehydrogenase. Czech. (1992), 4 pp.
2. Yamamoto T, Moriwaki Y, Takahashi S, Suda M, Higashino K: Ethanol as a xanthine dehydrogenase inhibitor. Metabolism. 1995 Jun;44(6):779-85.
3. 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.
4. 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.
5. 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.
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7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. Desir G, Bratusch-Marrain P, DeFronzo RA: Effect of hyperketonemia on renal ammonia excretion in man. Metabolism. 1986 Aug;35(8):736-43.
15. 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 (1985). 2000 Dec;89(6):2352-8.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. Biellmann JF, Lapinte C, Haid E, Weimann G: Structure of lactate dehydrogenase inhibitor generated from coenzyme. Biochemistry. 1979 Apr 3;18(7):1212-7.
23. 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.
24. 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.
25. 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.
26. 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.
27. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19.
28. WholeHealthMD: http://www.wholehealthmd.com/ME2/dirmod.asp?sid=17E09E7CFFF640448FFB0B4FC1B7FEF0&nm=Reference+Library&type=AWHN_Supplements&mod=Supplements&mid=&id=F8DDC620C82D41D1A6FBEDDD38337F63&tier=2
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=11259315
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=19459318