Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110540
Identification
Name: NADH
Description:Dianion of NADH arising from deprotonation of the two diphosphate OH groups; major species at pH 7.3.
Structure
Thumb
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 DescriptionThis 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 ClassOrganic 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
Physical Properties
State: Solid
Charge:-2
Melting point: 140.0 - 142.0 °C
Experimental Properties:
PropertyValueReference
Melting Point140.0 - 142.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.95 mg/mLALOGPS
logP-1.4ALOGPS
logP-6.5ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)-7ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area317.62 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity143 m3·mol-1ChemAxon
Polarizability57.65 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
UDP-N-acetyl-α-D-mannosamine + NAD+ + Water → UDP-N-acetyl-α-D-mannosaminouronate + NADH + Hydrogen ion
(S)-dihydroorotate + NAD+ → Hydrogen ion + orotate + NADH
L-lactaldehyde + NAD+ + Water → (S)-lactate + NADH + Hydrogen ion
3-hydroxy-5-trans-dodecenoyl-CoA + NAD+ → 5-trans-3-oxo-dodecenoyl-CoA + NADH + Hydrogen ion
3-ethylmalate + NAD+ → 2-oxovalerate + Carbon dioxide + NADH
UDP-α-D-glucuronate + NAD+ → UDP-4-Keto-pyranose + Carbon dioxide + NADH
4-acetamidobutanal + Water + NAD+ → 4-acetamidobutanoate + NADH + Hydrogen ion
3-oxopropanoate + coenzyme A + NAD+ → acetyl-CoA + Carbon dioxide + NADH
L-glutamate + Water + NAD+ → alpha-Ketoglutarate + Ammonium + NADH + Hydrogen ion
3-hydroxy- 5-cis, 7-trans-tetradecadienoyl-CoA + NAD+ → 5-cis, 7-trans-3-oxo-tetradecadienoyl-CoA + NADH + Hydrogen ion
2-phenylethanol + NAD+ → Hydrogen ion + phenylacetaldehyde + NADH
n-propanol + NAD+ → Propanal + NADH + Hydrogen ion
2-Keto-3-methyl-valerate + NAD+ + coenzyme A → 2-methylbutanoyl-CoA + NADH + Carbon dioxide
UDP-N-acetyl-α-D-glucosamine + NAD+ + Water → UDP-N-acetyl-α-D-glucosaminouronate + NADH + Hydrogen ion
D-threo-isocitrate + NAD+ → alpha-Ketoglutarate + Carbon dioxide + NADH
3-hydroxy, 4-trans-undecenoyl-CoA + NAD+ → 4-trans-3-oxo-undecenoyl-CoA + NADH + Hydrogen ion
indole-3-glycol + NAD+ → indole-3-glycol aldehyde + NADH + Hydrogen ion
6-hydroxycyclohex-1-ene-1-carbonyl-CoA + NAD+ → Hydrogen ion + 6-oxocyclohex-1-ene-1-carbonyl-CoA + NADH
L-3-HYDROXYACYL-COA + NAD+ → 3-KETOACYL-COA + NADH + Hydrogen ion
Secondary-Alcohols + NAD+ → LONG-CHAIN-KETONE + NADH + Hydrogen ion
Acetaldehyde + Water + NAD+ → acetate + NADH + Hydrogen ion
NAD+ + 2-methyl-3-hydroxybutyryl-CoA → Hydrogen ion + NADH + 2-methylacetoacetyl-CoA
OPC8-3-hydroxyacyl-CoA + NAD+ → OPC8-3-ketoacyl-CoA + NADH + Hydrogen ion
3-hydroxy, 6-trans-tridecenoyl-CoA + NAD+ → 6-trans-3-oxo-tridecenoyl-CoA + NADH + Hydrogen ion
OPC6-3-hydroxyacyl-CoA + NAD+ → OPC6-3-ketoacyl-CoA + NADH + Hydrogen ion
Propanal + coenzyme A + NAD+ → propanoyl-CoA + NADH + Hydrogen ion
2-methylbutanol + NAD+ → Hydrogen ion + 2-methylbutanal + NADH
precorrin-2 + NAD+ → Hydrogen ion + sirohydrochlorin + NADH
OPC4-3-hydroxyacyl-CoA + NAD+ → OPC4-3-ketoacyl-CoA + NADH + Hydrogen ion
3-hydroxy, 6-cis-tridecenoyl-CoA + NAD+ → 6-cis, 3-oxo-tridecenoyl-CoA + NADH + Hydrogen ion
androsta-1,4-diene-3,17-dione + Oxygen + NADH + Hydrogen ion → 9α-hydroxyandrosta-1,4-diene-3,17-dione + NAD+ + Water
3-(4-hydroxyphenyl)-3-hydroxy-propanoyl-CoA + NAD+ → 4-hydroxybenzoyl-acetyl-CoA + NADH + Hydrogen ion
(S)-3-hydroxyhexadecanoyl-CoA + NAD+ → 3-oxo-palmitoyl-CoA + NADH + Hydrogen ion
5-hydroxytryptophol + NAD+ → 5-hydroxyindole acetaldehyde + NADH + Hydrogen ion
phytol + NAD+ → phytenal + NADH + Hydrogen ion
phytenal + NAD+ + Water → phytenate + NADH + Hydrogen ion
3,5-cyclohexadiene-1,2-diol-1-carboxylate + NAD+ → catechol + Carbon dioxide + NADH
3-hydroxy-5-cis-tetradecenoyl-CoA + NAD+ → 3-keto-5-cis-tetradecenoyl-CoA + NADH + Hydrogen ion
vanillin + Water + NAD+ → vanillate + NADH + Hydrogen ion
Long-Chain-3S-Hydroxyacyl-CoAs + NAD+ → Long-Chain-oxoacyl-CoAs + NADH + Hydrogen ion
2-Me-Branched-234-Sat-FALD + NAD+ + Water → 2-Me-Branched-234-Sat-FA + NADH + Hydrogen ion
3-methoxy-4-hydroxyphenylglycol + NAD+ → 3-methoxy-4-hydroxyphenylglycolaldehyde + NADH + Hydrogen ion
Odd-Straight-Chain-234-Sat-FALD + NAD+ + Water → Odd-Straight-Chain-234-Sat-FA + NADH + Hydrogen ion
NAD+ + D-mannitol → aldehydo-D-mannose + Hydrogen ion + NADH
n-butanol + NAD+ → Butanal + NADH + Hydrogen ion
NADP+ + NADH + Hydrogen ion → NADPH + NAD+ + Hydrogen ion
NADH + Hydrogen ion + Ubiquinones + NA+ → NAD+ + Ubiquinols + NA+
D-3-HYDROXYACYL-COA + NAD+ → 3-KETOACYL-COA + NADH + Hydrogen ion
NADH + Hydrogen ion + ETR-Quinones → NAD+ + ETR-Quinols
sn-glycerol 3-phosphate + NAD+ → glycerone phosphate + NADH + Hydrogen ion
(S)-3-hydroxyhexanoyl-CoA + NAD+ → 3-oxohexanoyl-CoA + NADH + Hydrogen ion
Aldehydes + NAD+ + Water → Carboxylates + NADH + Hydrogen ion
Ubiquinones + Hydrogen ion + NADH → Ubiquinols + NAD+
FMNH(2) + NAD+ → FMN + NADH + Hydrogen ion
3-hydroxyadipyl-CoA + NAD+ → Hydrogen ion + 3-oxoadipyl-CoA + NADH
3-methylbutanol + NAD+ → Hydrogen ion + 3-methylbutanal + NADH
Menaquinone + NADH + Hydrogen ion → menadiol + NAD+
D-arabitol + NAD+ → D-xylulose + NADH + Hydrogen ion
cobalt-precorrin-6B + NAD+ → cobalt-precorrin-6A + NADH
5,6-dihydrouracil + NAD+ → Uracil + NADH + Hydrogen ion
vanillate + Oxygen + NADH + Hydrogen ion → protocatechuate + Formaldehyde + NAD+ + Water
24-hydroxy-3-oxocholest-4-en-26-oyl-CoA + NAD+ → 3,24-dioxocholest-4-en-26-oyl-CoA + NADH + Hydrogen ion
salicylaldehyde + NAD+ + Water → salicylate + NADH + Hydrogen ion
UDP-N-acetyl-α-D-glucosaminouronate + NAD+ → UDP-2-acetamido-2-deoxy-α-D-ribo-hex-3-uluronate + NADH + Hydrogen ion
histidinol + NAD+ + Water → L-Histidine + NADH + Hydrogen ion
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0931104000-bf6579d19ee9bc297e13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-92672b1d4b96838f8652View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-ef56d203da65089e145fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03e9-1900207000-f248eb28a7283de7118bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900100000-efadf1d6c54e9e86671dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-3900000000-f258fc2bf1d8e54ac6daView in MoNA
References
References:
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  • 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) Download (PDF)
External Links:
ResourceLink
CAS58-68-4
ChEBI57945
ChemSpider10239197
HMDBHMDB01487
IAF126033484
KEGGC00004
MetaboLightsMTBLC57945
PubChem21604869