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Showing Compound NADH (FDB022649)

Record Information
Version1.0
Creation date2011-09-21 00:17:25 UTC
Update date2019-11-26 03:21:05 UTC
Primary IDFDB022649
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNADH
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 (NADH). 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) [HMDB]. NADH is found in many foods, some of which are dill, ohelo berry, fox grape, and black-eyed pea.
CAS Number58-68-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Dihydronicotinamide formycin dinucleotideMeSH
NFDHMeSH
1,4-Dihydronicotinamide adenine dinucleotidehmdb
b-DPNHhmdb
b-NADHhmdb
beta-DPNHhmdb
beta-NADHhmdb
Dihydrocodehydrogenase Ihmdb
Dihydrocozymasehmdb
Dihydronicotinamide adenine dinucleotidehmdb
Dihydronicotinamide mononucleotidehmdb
DPNHhmdb
ENADAhmdb
NADHhmdb
NADH2hmdb
Nicotinamide adenine dinucleotide (reduced)ChEBI
Reduced codehydrogenase Ihmdb
Reduced diopyridine nucleotideHMDB
Reduced diphosphopyridine nucleotidehmdb
Reduced nicotinamide adenine diateHMDB
Reduced nicotinamide adenine dinucleotideChEBI
Reduced nicotinamide adenine diphosphatehmdb
Reduced nicotinamide-adenine dinucleotidehmdb
Predicted Properties
PropertyValueSource
Water Solubility4.3 g/LALOGPS
logP-1.7ALOGPS
logP-7.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.48ChemAxon
pKa (Strongest Basic)12.02ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area318.61 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity153.94 m³·mol⁻¹ChemAxon
Polarizability59.26 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H29N7O14P2
IUPAC name1-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}-1,4-dihydropyridine-3-carboximidic acid
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
Isomeric 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
Average Molecular Weight665.441
Monoisotopic Molecular Weight665.124771695
Classification
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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00n0-0210192000-bf07b6b154c5778067ce2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0150291000-84ef746651797f0679a52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-0970000000-0688003193d7fc4612352012-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03e9-1900207000-035683a7096e705be3f32015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900100000-205fe57090902cf7bf682015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-3900000000-5bde95578282a7afb0132015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0930104000-0770b191623eb0601d772015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-122ca14f9d6fd72a943b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-182ea032481073c4434c2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID903
ChEMBL IDNot Available
KEGG Compound IDC00004
Pubchem Compound ID439153
Pubchem Substance IDNot Available
ChEBI ID16908
Phenol-Explorer IDNot Available
DrugBank IDDB00157
HMDB IDHMDB01487
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33484
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNADH
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Aminoadipate-semialdehyde synthaseAASSA4D0W4
Aminomethyltransferase, mitochondrialAMTP48728
Glycine cleavage system H protein, mitochondrialGCSHP23434
Alcohol dehydrogenase [NADP(+)]AKR1A1P14550
7-dehydrocholesterol reductaseDHCR7Q9UBM7
Pyruvate dehydrogenase E1 component subunit beta, mitochondrialPDHBP11177
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrialPDHA1P08559
Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrialPDHA2P29803
2-oxoglutarate dehydrogenase, mitochondrialOGDHQ02218
2-oxoglutarate dehydrogenase-like, mitochondrialOGDHLQ9ULD0
MOSC domain-containing protein 2, mitochondrialMOSC2Q969Z3
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrialDLATP10515
Testosterone 17-beta-dehydrogenase 3HSD17B3P37058
GDP-mannose 4,6 dehydrataseGMDSO60547
C-1-tetrahydrofolate synthase, cytoplasmicMTHFD1P11586
Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolaseMTHFD2Q7Z650
Acyl-CoA synthetase family member 4AASDHQ4L235
L-aminoadipate-semialdehyde dehydrogenase-phosphopantetheinyl transferaseAASDHPPTQ9NRN7
Inosine-5'-monophosphate dehydrogenaseIMPDH1A4D0Z6
Dihydrofolate reductaseDHFRP00374
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 1NDUFB1O75438
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 12NDUFA12Q9UI09
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 1NDUFA1O15239
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 4-like 2NDUFA4L2Q9NRX3
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 3NDUFA3O95167
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 8NDUFA8P51970
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 4NDUFA4O00483
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 11NDUFA11Q86Y39
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 6NDUFA6P56556
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 4NDUFB4O95168
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 7NDUFA7O95182
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 2NDUFA2O43678
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 5, mitochondrialNDUFB5O43674
NADH dehydrogenase [ubiquinone] 1 subunit C2NDUFC2O95298
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 3NDUFB3O43676
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 7NDUFB7P17568
Acyl carrier protein, mitochondrialNDUFAB1O14561
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 5NDUFA5Q16718
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 9NDUFB9Q9Y6M9
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 13NDUFA13Q9P0J0
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 11, mitochondrialNDUFB11Q9NX14
NADH dehydrogenase (Ubiquinone) 1 beta subcomplex, 2, 8kDaNDUFB2A4D1T5
Dehydrogenase/reductase SDR family member 9DHRS9Q9BPW9
Corticosteroid 11-beta-dehydrogenase isozyme 1HSD11B1P28845
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 10NDUFB10O96000
NADH dehydrogenase [ubiquinone] flavoprotein 3, mitochondrialNDUFV3P56181
NADH dehydrogenase [ubiquinone] 1 subunit C1, mitochondrialNDUFC1O43677
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 6NDUFB6O95139
NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 8, mitochondrialNDUFB8O95169
Complex I intermediate-associated protein 30, mitochondrialNDUFAF1Q9Y375
Evolutionarily conserved signaling intermediate in Toll pathway, mitochondrialECSITQ9BQ95
NADH dehydrogenase [ubiquinone] 1 alpha subcomplex assembly factor 4NDUFAF4Q9P032
Mimitin, mitochondrialNDUFAF2Q8N183
Pathways
NameSMPDB LinkKEGG Link
Ammonia RecyclingSMP00009 map00910
Carnitine SynthesisSMP00465 Not Available
Citric Acid CycleSMP00057 map00020
Ethanol DegradationSMP00449 Not Available
Folate MetabolismSMP00053 map00670
GluconeogenesisSMP00128 map00010
Glucose-Alanine CycleSMP00127 Not Available
Glycerol Phosphate ShuttleSMP00124 Not Available
Glycerolipid MetabolismSMP00039 map00561
Glycine and Serine MetabolismSMP00004 map00260
GlycolysisSMP00040 map00010
Histidine MetabolismSMP00044 map00340
Ketone Body MetabolismSMP00071 map00072
Malate-Aspartate ShuttleSMP00129 Not Available
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsSMP00482 Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty AcidsSMP00481 Not Available
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty AcidsSMP00480 Not Available
Mitochondrial Electron Transport ChainSMP00355 map00190
Plasmalogen SynthesisSMP00479 Not Available
Threonine and 2-Oxobutanoate DegradationSMP00452 Not Available
Transfer of Acetyl Groups into MitochondriaSMP00466 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference