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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:57:20 UTC
HMDB IDHMDB0000902
Secondary Accession Numbers
  • HMDB00902
Metabolite Identification
Common 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 either converted into 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 via cellular respiration (Wikipedia ). NAD is a coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by a 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).
Structure
Data?1600191188
Synonyms
ValueSource
Codehydrogenase IChEBI
Coenzyme IChEBI
Cozymase IChEBI
Diphosphopyridine nucleotideChEBI
DPNChEBI
NadideChEBI
NICOTINAMIDE-adenine-dinucleotideChEBI
Adenine dinucleotide, dihydronicotinamideMeSH
NADMeSH
Nicotinamide-adenine dinucleotideMeSH
Nucleotide, diphosphopyridineMeSH
Dihydronicotinamide adenine dinucleotideMeSH
NADHMeSH
Nicotinamide adenine dinucleotideMeSH
Dinucleotide, nicotinamide-adenineMeSH
Dinucleotide, dihydronicotinamide adenineMeSH
Adenine-nicotinamide dinucleotideHMDB
NAD+HMDB
Oxidized diphosphopyridine nucleotideHMDB
beta-Diphosphopyridine nucleotideHMDB
beta-NADHMDB
beta-NAD+HMDB
beta-Nicotinamide adenine dinucleotideHMDB
beta-Nicotinamide adenine dinucleotide hydrateHMDB
β-Diphosphopyridine nucleotideHMDB
β-NADHMDB
β-NAD+HMDB
β-Nicotinamide adenine dinucleotideHMDB
β-Nicotinamide adenine dinucleotide hydrateHMDB
Chemical FormulaC21H27N7O14P2
Average Molecular Weight663.4251
Monoisotopic Molecular Weight663.109121631
IUPAC Name1-[(2R,3R,4S,5R)-5-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy)(hydroxy)phosphoryl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium
Traditional Name1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium
CAS Registry Number53-84-9
SMILES
NC(=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
InChI Identifier
InChI=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)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChI KeyBAWFJGJZGIEFAR-NNYOXOHSSA-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
  • 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
  • Organic zwitterion
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140.0 - 142.0 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility752.5 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg226.330932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.81 g/LALOGPS
logP-1.2ALOGPS
logP-10ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)6.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area322.08 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity151.81 m³·mol⁻¹ChemAxon
Polarizability58.5 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+214.29830932474
DeepCCS[M-H]-212.64430932474
DeepCCS[M-2H]-246.6830932474
DeepCCS[M+Na]+220.45530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NADNC(=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]1O5442.7Standard polar33892256
NADNC(=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]1O3667.4Standard non polar33892256
NADNC(=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]1O5742.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_17) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAD GC-MS (TMS_2_18) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-03di-0000029000-870aa620464a4fedbe8d2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-002r-0930610000-ccd233f26036136ba3e82019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000i-0900000000-ec77ba41ae7dbcfd08a22019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-00dl-0219003700-2f52e3c5db41066a112c2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0uk9-0301009000-a3d0c464e56f6e320c802019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-00dl-0000090000-c18a7719161c63a719382019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0udi-0000009000-1dde5b221786fe3753042019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0002-0911001000-bd16ca8021ab63e9e2902019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-001i-0900000000-662adda5a00fce5c50172019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-03di-0900000000-a2724dbab2ca6eb7e8da2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-00dl-0400090000-19bb49ef6fe960f224d22019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-006x-0011297400-efee4fe3a4cf024c960a2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-004i-0028900000-8ec9bcaf25513495b9792019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0a4i-0011953000-577487fb6aff29c773302019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-00di-0000009000-e1d0afb4e7926a0f845e2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0006-0001092010-1dcbca7a5ffe61f23e502019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-004i-0028900000-764e3ecea72fe178a87e2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-004i-0018900000-3b774fba9b96129baa6c2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NAD LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0006-0000090000-d4236efb9eec360174162019-11-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAD 10V, Positive-QTOFsplash10-03di-0000009000-3cb1cc8e613a3e1791492016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAD 20V, Positive-QTOFsplash10-014j-0000009000-4bd400c0be81ab9384652016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAD 40V, Positive-QTOFsplash10-0006-6920102000-5fc300f474c5dc2b86002016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAD 10V, Negative-QTOFsplash10-03di-0000009000-96d7faa48cdd181798a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAD 20V, Negative-QTOFsplash10-03di-1100109000-f496601a0ac75ae3d4a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAD 40V, Negative-QTOFsplash10-003s-9201000000-c06274c9b4d1b70a9ce22016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2019-11-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Nucleus
  • Endoplasmic reticulum
  • Peroxisome
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
Tissue Locations
  • Adrenal Gland
  • Brain
  • Epidermis
  • Fibroblasts
  • Liver
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified24.3 (23.0-25.6) uMAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified88.7 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0036 uMInfant (0-1 year old)FemaleNicotinamide Adenine Dinucleotide Deficiency details
BloodDetected and Quantified29.1 (25.0-33.2) uMAdult (>18 years old)BothPellagra details
Associated Disorders and Diseases
Disease References
Pellagra
  1. Creeke PI, Dibari F, Cheung E, van den Briel T, Kyroussis E, Seal AJ: Whole blood NAD and NADP concentrations are not depressed in subjects with clinical pellagra. J Nutr. 2007 Sep;137(9):2013-7. [PubMed:17709435 ]
Nicotinamide Adenine Dinucleotide Deficiency
  1. Shi H, Enriquez A, Rapadas M, Martin EMMA, Wang R, Moreau J, Lim CK, Szot JO, Ip E, Hughes JN, Sugimoto K, Humphreys DT, McInerney-Leo AM, Leo PJ, Maghzal GJ, Halliday J, Smith J, Colley A, Mark PR, Collins F, Sillence DO, Winlaw DS, Ho JWK, Guillemin GJ, Brown MA, Kikuchi K, Thomas PQ, Stocker R, Giannoulatou E, Chapman G, Duncan EL, Sparrow DB, Dunwoodie SL: NAD Deficiency, Congenital Malformations, and Niacin Supplementation. N Engl J Med. 2017 Aug 10;377(6):544-552. doi: 10.1056/NEJMoa1616361. [PubMed:28792876 ]
Associated OMIM IDsNone
DrugBank IDDB14128
Phenol Explorer Compound IDNot Available
FooDB IDFDB022309
KNApSAcK IDC00007256
Chemspider ID5682
KEGG Compound IDC00003
BioCyc IDNAD
BiGG IDNot Available
Wikipedia LinkNicotinamide_adenine_dinucleotide
METLIN IDNot Available
PubChem Compound5892
PDB IDNot Available
ChEBI ID44215
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHughes, N. A.; Kenner, G. W.; Todd, Alexander. Codehydrogenases. III. Synthesis of diphosphopyridine nucleotide (cozymase) and triphosphopyridine nucleotide. Journal of the Chemical Society (1957), 3733-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Brautigam CA, Chuang JL, Tomchick DR, Machius M, Chuang DT: Crystal structure of human dihydrolipoamide dehydrogenase: NAD+/NADH binding and the structural basis of disease-causing mutations. J Mol Biol. 2005 Jul 15;350(3):543-52. [PubMed:15946682 ]
  2. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  3. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
  4. Ying W: NAD+ and NADH in cellular functions and cell death. Front Biosci. 2006 Sep 1;11:3129-48. [PubMed:16720381 ]
  5. Hamza A, Cho H, Tai HH, Zhan CG: Understanding human 15-hydroxyprostaglandin dehydrogenase binding with NAD+ and PGE2 by homology modeling, docking and molecular dynamics simulation. Bioorg Med Chem. 2005 Jul 15;13(14):4544-51. [PubMed:15908215 ]
  6. Begonja AJ, Gambaryan S, Geiger J, Aktas B, Pozgajova M, Nieswandt B, Walter U: Platelet NAD(P)H-oxidase-generated ROS production regulates alphaIIbbeta3-integrin activation independent of the NO/cGMP pathway. Blood. 2005 Oct 15;106(8):2757-60. Epub 2005 Jun 23. [PubMed:15976180 ]
  7. Bruzzone S, Moreschi I, Guida L, Usai C, Zocchi E, De Flora A: Extracellular NAD+ regulates intracellular calcium levels and induces activation of human granulocytes. Biochem J. 2006 Feb 1;393(Pt 3):697-704. [PubMed:16225456 ]
  8. Kim MY, Zhang T, Kraus WL: Poly(ADP-ribosyl)ation by PARP-1: 'PAR-laying' NAD+ into a nuclear signal. Genes Dev. 2005 Sep 1;19(17):1951-67. [PubMed:16140981 ]
  9. Kunsman GW, Manno JE, Cockerham KR, Manno BR: A modification and validation of two urine ethanol procedures for use with the Monarch 2000 Chemistry System. J Anal Toxicol. 1991 May-Jun;15(3):130-5. [PubMed:1943056 ]
  10. Orczyk J, Morre DM, Morre DJ: Periodic fluctuations in oxygen consumption comparing HeLa (cancer) and CHO (non-cancer) cells and response to external NAD(P)+/NAD(P)H. Mol Cell Biochem. 2005 May;273(1-2):161-7. [PubMed:16013451 ]
  11. 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. [PubMed:12130503 ]
  12. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 261 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHB
Uniprot ID:
P11177
Molecular weight:
39233.1
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHA1
Uniprot ID:
P08559
Molecular weight:
43295.255
Reactions
Coenzyme A + NAD + Pyruvic acid → Carbon dioxide + Hydrogen Ion + NADH + Acetyl-CoAdetails
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHA2
Uniprot ID:
P29803
Molecular weight:
42932.855
General function:
Involved in oxidoreductase activity
Specific function:
Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:
ALDH6A1
Uniprot ID:
Q02252
Molecular weight:
57839.31
Reactions
2-Methyl-3-oxopropanoic acid + Coenzyme A + Water + NAD → Propionyl-CoA + Hydrogen carbonate + NADHdetails
Malonic semialdehyde + Coenzyme A + NAD → Acetyl-CoA + Carbon dioxide + NADH + Hydrogen Iondetails
(S)-Methylmalonic acid semialdehyde + Coenzyme A + NAD → Propionyl-CoA + Carbon dioxide + NADH + Hydrogen Iondetails
(S)-Methylmalonic acid semialdehyde + Coenzyme A + NAD → Methylmalonyl-CoA + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes. Involved in the hyperactivation of spermatazoa during capacitation and in the spermatazoal acrosome reaction.
Gene Name:
DLD
Uniprot ID:
P09622
Molecular weight:
54176.91
Reactions
Protein N(6)-(dihydrolipoyl)lysine + NAD → protein N(6)-(lipoyl)lysine + NADHdetails
Dihydrolipoamide + NAD → Lipoamide + NADH + Hydrogen Iondetails
Dihydrolipoylprotein + NAD → Lipoylprotein + NADH + Hydrogen Iondetails
Enzyme N6-(dihydrolipoyl)lysine + NAD → Enzyme N6-(lipoyl)lysine + NADH + Hydrogen Iondetails
Coenzyme A + NAD + Pyruvic acid → Carbon dioxide + Hydrogen Ion + NADH + Acetyl-CoAdetails
General function:
Involved in acyltransferase activity
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
DLAT
Uniprot ID:
P10515
Molecular weight:
68996.03
Reactions
Coenzyme A + NAD + Pyruvic acid → Carbon dioxide + Hydrogen Ion + NADH + Acetyl-CoAdetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Reactions
Androsterone + NAD → Androstanedione + NADH + Hydrogen Iondetails
Etiocholanolone + NAD → Etiocholanedione + NADH + Hydrogen Iondetails
3a,7a-Dihydroxy-5b-cholestane + NAD → 7a-Hydroxy-5b-cholestan-3-one + NADH + Hydrogen Iondetails
5beta-Cholestane-3alpha,7alpha,12alpha-triol + NAD → 7a,12a-Dihydroxy-5b-cholestan-3-one + NADH + Hydrogen Iondetails
Tetrahydrocortisone + NAD → 17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + NADH + Hydrogen Iondetails
Tetrahydrocortisol + NAD → Dihydrocortisol + NADH + Hydrogen Iondetails
3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al + NAD → 11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADH + Hydrogen Iondetails
Tetrahydrocorticosterone + NAD → 11b,21-Dihydroxy-5b-pregnane-3,20-dione + NADH + Hydrogen Iondetails
3a,21-Dihydroxy-5b-pregnane-11,20-dione + NAD → 21-Hydroxy-5b-pregnane-3,11,20-trione + NADH + Hydrogen Iondetails
3a-Hydroxy-5b-pregnane-20-one + NAD → 5a-Pregnane-3,20-dione + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Prostaglandin inactivation. Contributes to the regulation of events that are under the control of prostaglandin levels. Catalyzes the NAD-dependent dehydrogenation of lipoxin A4 to form 15-oxo-lipoxin A4. Inhibits in vivo proliferation of colon cancer cells.
Gene Name:
HPGD
Uniprot ID:
P15428
Molecular weight:
28977.105
Reactions
(5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD → (5Z,13E)-11-alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADHdetails
General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69
Reactions
Tyramine + Oxygen + NADH + Hydrogen Ion → Dopamine + NAD + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125
Reactions
Glycerol + NAD → Glyceraldehyde + NADH + Hydrogen Iondetails
beta-D-Galactose + NADH + Hydrogen Ion → Galactitol + NADdetails
L-Arabitol + NAD → L-Arabinose + NADH + Hydrogen Iondetails
Lactaldehyde + NAD → Pyruvaldehyde + NADH + Hydrogen Iondetails

Only showing the first 10 proteins. There are 261 proteins in total.