NADH (CED0000620)

Record Information
Version1.0
Creation Date2016-05-26 05:36:02 UTC
Update Date2026-05-14 16:24:21 UTC
Accession NumberCHEM035239
Identification
Common NameNADH
ClassSmall Molecule
Description
NADH is an organic compound with the chemical formula C21H29N7O14P2. NADH belongs to the (5'->5')-dinucleotides, a class of nucleosides, nucleotides, and analogues within the organic compounds. With an average molecular weight of 665.44 g/mol, NADH is a heavy molecule. The compound is associated with 144 recorded protein targets. These include Alcohol dehydrogenase 1A (ADH1A), Sorbitol dehydrogenase (SORD), All-trans-retinol dehydrogenase [NAD(+)] ADH4, and a binder of UDP-glucose 6-dehydrogenase (UGDH), along with 140 other proteins. Additionally, NADH is found in or released from three recorded sources, specifically Electrical & Electronic Equipment including conductors or conductive bodies characterised by the conductive materials, antennas, and amplifiers.
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrumsplash10-00n0-0210192000-bf07b6b154c5778067ceNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0150291000-84ef746651797f0679a5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0970000000-0688003193d7fc461235Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0930104000-0770b191623eb0601d77Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0901000000-122ca14f9d6fd72a943bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-182ea032481073c4434cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03e9-1900207000-035683a7096e705be3f3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1900100000-205fe57090902cf7bf68Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a7i-3900000000-5bde95578282a7afb013Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
Pathways
157345 pathways
beta-Alanine Metabolism
beta-Alanine Metabolism
GABA-Transaminase Deficiency
GABA-Transaminase Deficiency
Carnosinuria, Carnosinemia
Carnosinuria, Carnosinemia
GABA-Transaminase Deficiency: beta-alanine
GABA-Transaminase Deficiency: beta-alanine
beta-Aminoisobutyric Aciduria
beta-Aminoisobutyric Aciduria
Carnosinuria, Carnosinemia
Carnosinuria, Carnosinemia
Cysteine Metabolism
Cysteine Metabolism
beta-Mercaptolactate-Cysteine Disulfiduria
beta-Mercaptolactate-Cysteine Disulfiduria
Cystinosis, Ocular Nonnephropathic
Cystinosis, Ocular Nonnephropathic
beta-Mercaptolactate-Cysteine Disulfiduria
beta-Mercaptolactate-Cysteine Disulfiduria
Cystinosis, Ocular Nonnephropathic
Cystinosis, Ocular Nonnephropathic
Cyclophosphamide Action Pathway
Cyclophosphamide Action Pathway
View all 157345 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureGlutamate dehydrogenase 1, mitochondrialP00366Bos taurusPredicted (SEA)0.0778492
P2Y purinoceptor 1 structureClick to view 3D structureP2Y purinoceptor 1P47900HumansPredicted (SEA)0.700643
P2X purinoceptor 1 structureClick to view 3D structureP2X purinoceptor 1P51575HumansPredicted (SEA)0.544945
Click to view 3D structureP2Y purinoceptor 2P41231HumansPredicted (SEA)2.49118
ADP-ribose glycohydrolase MACROD1 structureClick to view 3D structureADP-ribose glycohydrolase MACROD1Q9BQ69HumansPredicted (SEA)0.389246
ADP-ribose glycohydrolase MACROD2 structureClick to view 3D structureADP-ribose glycohydrolase MACROD2A1Z1Q3HumansPredicted (SEA)0.389246
Click to view 3D structureHeat shock cognate 71 kDa proteinP19120Bos taurusPredicted (SEA)0.700643
Click to view 3D structureSensor protein kinase WalKQ9RDT3Staphylococcus aureusPredicted (SEA)0.700643
P2X purinoceptor 3 structureClick to view 3D structureP2X purinoceptor 3P56373HumansPredicted (SEA)0.622794
Click to view 3D structureP2Y purinoceptor 1P49652Meleagris gallopavoPredicted (SEA)0.778492
Click to view 3D structureGTP:AMP phosphotransferase AK3, mitochondrialP29411Rattus norvegicusPredicted (SEA)0.467095
Click to view 3D structureP2Y purinoceptor 12Q9EPX4Rattus norvegicusPredicted (SEA)0.467095
Click to view 3D structureP2Y purinoceptor 11Q96G91HumansPredicted (SEA)0.856341
Click to view 3D structureS-adenosylmethionine synthase isoform type-2P18298Rattus norvegicusPredicted (SEA)0.544945
Click to view 3D structureP2Y purinoceptor 1P49651Rattus norvegicusPredicted (SEA)0.700643
Click to view 3D structureAdenylate kinase 2, mitochondrialP29410Rattus norvegicusPredicted (SEA)0.544945
P2X purinoceptor 4 structureClick to view 3D structureP2X purinoceptor 4Q99571HumansPredicted (SEA)0.622794
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 structureClick to view 3D structureEctonucleotide pyrophosphatase/phosphodiesterase family member 1P22413HumansPredicted (SEA)1.01204
Click to view 3D structureGlutamine--tRNA ligaseP00962Escherichia coli (strain K12)Predicted (SEA)0.778492
Click to view 3D structurePoly(ADP-ribose) glycohydrolaseO02776Bos taurusPredicted (SEA)0.311397
Click to view 3D structureP2X purinoceptor 2P49653Rattus norvegicusPredicted (SEA)1.55698
Click to view 3D structureP2X purinoceptor 4P51577Rattus norvegicusPredicted (SEA)1.47914
Click to view 3D structureInosine-5'-monophosphate dehydrogenase 2P24547Mus musculusPredicted (SEA)0.778492
Click to view 3D structureP2X purinoceptor 6P51579Rattus norvegicusPredicted (SEA)0.778492
Click to view 3D structureP2X purinoceptor 5P51578Rattus norvegicusPredicted (SEA)0.700643
Concentrations
Not Available
External Links
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
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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.
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29. https://www.ncbi.nlm.nih.gov/pubmed/?term=11259315
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