Record Information
Version1.0
Creation date2011-09-21 00:11:54 UTC
Update date2015-10-09 22:32:35 UTC
Primary IDFDB022309
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNAD
DescriptionNAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a 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). (Dorland, 27th ed) [HMDB]
CAS Number53-84-9
Structure
Thumb
Synonyms
SynonymSource
beta-NADChEBI
Diphosphopyridine nucleotideChEBI
DPNChEBI
NAD+ChEBI
NadideChEBI
Nicotinamide adenine dinucleotideChEBI
beta-NAD+Kegg
b-NADGenerator
Β-nadGenerator
b-NAD+Generator
Β-nad+Generator
3-Carbamoyl-1-beta-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner saltHMDB
3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner saltHMDB
3-Carbamoyl-1-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphateHMDB
3-Carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphateHMDB
Adenine-nicotinamide dinucleotideHMDB
beta-Diphosphopyridine nucleotideHMDB
beta-Nicotinamide adenine dinucleotideHMDB
beta-Nicotinamide adenine dinucleotide trihydrateHMDB
CO-IHMDB
Codehydrase IHMDB
Codehydrogenase IHMDB
Coenzyme IHMDB
CozymaseHMDB
Cozymase IHMDB
Diphosphopyridine nucleotide oxidizedHMDB
EndoprideHMDB
NAD trihydrateHMDB
NAD-oxidizedHMDB
Nicotinamide adenine dinucleotide oxidizedHMDB
Nicotinamide dinucleotideHMDB
Nicotineamide adenine dinucleotideHMDB
Oxidized diphosphopyridine nucleotideHMDB
Pyridine nucleotide diphosphateHMDB
[(3S,2R,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3S,2R,4R,5R)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphateHMDB
[Adenylate-32-p]-NADHMDB
Dihydronicotinamide adenine dinucleotideHMDB
NADHHMDB
Nucleotide, diphosphopyridineHMDB
Adenine dinucleotide, dihydronicotinamideHMDB
Dinucleotide, dihydronicotinamide adenineHMDB
Dinucleotide, nicotinamide-adenineHMDB
Nicotinamide-adenine dinucleotideHMDB
[(3S,2R,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3S,2R,4R,5R)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyoryl) hydrogen ateHMDB
[adenylate-32-P]-NADhmdb
3-Carbamoyl-1-beta-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyroate inner saltHMDB
3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyroate inner saltHMDB
3-Carbamoyl-1-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyroateHMDB
3-Carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyroateHMDB
beta-Diopyridine nucleotideHMDB
Diopyridine nucleotideChEBI
Diopyridine nucleotide oxidizedHMDB
diphosphopyridine nucleotide oxidizedhmdb
nicotinamide adenine dinucleotide oxidizedhmdb
Oxidized diopyridine nucleotideHMDB
Pyridine nucleotide diateHMDB
Predicted Properties
PropertyValueSource
Water Solubility1.81 g/LALOGPS
logP-1.2ALOGPS
logP-9.9ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area318.26 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity142 m³·mol⁻¹ChemAxon
Polarizability55.83 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H28N7O14P2
IUPAC name1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-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]-3-carbamoyl-1lambda5-pyridin-1-ylium
InChI IdentifierInChI=1S/C21H27N7O14P2/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/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChI KeyBAWFJGJZGIEFAR-NNYOXOHSSA-O
Isomeric SMILESNC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
Average Molecular Weight664.433
Monoisotopic Molecular Weight664.116946663
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
  • Pyridine nucleotide
  • Pentose-5-phosphate
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Purine
  • Imidazopyrimidine
  • Nicotinamide
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Imidolactam
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Pyridinium
  • Pyridine
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-4213904000-b8a6dbd0370f9d5a56beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0000029000-870aa620464a4fedbe8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002r-0930610000-ccd233f26036136ba3e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-0900000000-ec77ba41ae7dbcfd08a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00dl-0219003700-2f52e3c5db41066a112cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-0301009000-a3d0c464e56f6e320c80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00dl-0000090000-c18a7719161c63a71938View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0000009000-1dde5b221786fe375304View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0911001000-bd16ca8021ab63e9e290View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-662adda5a00fce5c5017View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-a2724dbab2ca6eb7e8daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00dl-0400090000-19bb49ef6fe960f224d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-006x-0011297400-efee4fe3a4cf024c960aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0028900000-8ec9bcaf25513495b979View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0011953000-577487fb6aff29c77330View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0000009000-e1d0afb4e7926a0f845eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0001092010-1dcbca7a5ffe61f23e50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0028900000-764e3ecea72fe178a87eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0018900000-3b774fba9b96129baa6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0000090000-d4236efb9eec36017416View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-b658a57d72fd6ec693f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0000009000-841f81c695ad2c0ec387View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-7920202000-c7820b4eaef53b5cdf66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000009000-0b37b39334338eb59ba4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1100109000-7b9f7c9d8d96bfbfe848View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01rt-9300000000-34fd3df485912f4e75a4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID5682
ChEMBL IDNot Available
KEGG Compound IDC00003
Pubchem Compound ID5893
Pubchem Substance IDNot Available
ChEBI ID15846
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00902
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33480
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNAD
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
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrialDLATP10515
14 kDa phosphohistidine phosphatasePHPT1Q9NRX4
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
Corticosteroid 11-beta-dehydrogenase isozyme 1HSD11B1P28845
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
Glutamate MetabolismSMP00072 map00250
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
Nicotinate and Nicotinamide MetabolismSMP00048 map00760
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