Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:33 UTC
HMDB IDHMDB00902
Secondary Accession NumbersNone
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 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).
Structure
Thumb
Synonyms
  1. 3-Carbamoyl-1-beta-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt
  2. 3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt
  3. 3-Carbamoyl-1-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate
  4. 3-Carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate
  5. Adenine-nicotinamide dinucleotide
  6. beta-Diphosphopyridine nucleotide
  7. beta-NAD
  8. beta-Nicotinamide adenine dinucleotide
  9. beta-Nicotinamide adenine dinucleotide trihydrate
  10. CO-I
  11. Codehydrase I
  12. Codehydrogenase I
  13. Coenzyme I
  14. Cozymase
  15. Cozymase I
  16. Diphosphopyridine nucleotide
  17. Diphosphopyridine nucleotide oxidized
  18. Endopride
  19. NAD trihydrate
  20. NAD-oxidized
  21. Nicotinamide adenine dinucleotide
  22. Nicotinamide adenine dinucleotide oxidized
  23. Nicotinamide dinucleotide
  24. Nicotineamide adenine dinucleotide
  25. Oxidized diphosphopyridine nucleotide
  26. Pyridine nucleotide diphosphate
  27. [(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 phosphate
  28. [adenylate-32-P]-NAD
Chemical FormulaC21H28N7O14P2
Average Molecular Weight664.433
Monoisotopic Molecular Weight664.116946663
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-1$l^{5}-pyridin-1-ylium
Traditional IUPAC Name1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1$l^{5}-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)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChI KeyBAWFJGJZGIEFAR-NNYOXOHSSA-O
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • NAD(ChEBI)
  • NAD(P)(+)(ChEBI)
Substituents
  • 1,2 Diol
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Disaccharide Phosphate
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • N Glycosyl Compound
  • Nicotinamide Nucleotide
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Disaccharide
  • Phosphoric Acid Ester
  • Primary Carboxylic Acid Amide
  • Purine
  • Pyridine
  • Pyridine Nucleotide
  • Pyridinium
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
Direct ParentPurine Ribonucleoside Diphosphates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminosugars metabolism
  • Component of Androgen and estrogen metabolism
  • Component of Arginine and proline metabolism
  • Component of Ascorbate and aldarate metabolism
  • Component of Bile acid biosynthesis
  • Component of Butanoate metabolism
  • Component of C21-Steroid hormone metabolism
  • Component of Cysteine metabolism
  • Component of D-Glutamine and D-glutamate metabolism
  • Component of Fatty acid metabolism
  • Component of Folate biosynthesis
  • Component of Fructose and mannose metabolism
  • Component of Galactose metabolism
  • Component of Glutamate metabolism
  • Component of Glutathione metabolism
  • Component of Glycerolipid metabolism
  • Component of Glycerophospholipid metabolism
  • Component of Glycine, serine and threonine metabolism
  • Component of Glyoxylate and dicarboxylate metabolism
  • Component of Histidine metabolism
  • Component of Inositol metabolism
  • Component of Methane metabolism
  • Component of Nicotinate and nicotinamide metabolism
  • Component of Nitrogen metabolism
  • Component of Nucleotide sugars metabolism
  • Component of Phenylalanine metabolism
  • Component of Porphyrin and chlorophyll metabolism
  • Component of Propanoate metabolism
  • Component of Prostaglandin and leukotriene metabolism
  • Component of Purine metabolism
  • Component of Pyruvate metabolism
  • Component of Retinol metabolism
  • Component of Starch and sucrose metabolism
  • Component of Tryptophan metabolism
  • Component of Tyrosine metabolism
  • Component of Ubiquinone biosynthesis
  • Component of beta-Alanine metabolism
ApplicationNot Available
Cellular locations
  • Extracellular
  • Mitochondria
  • Nucleus
  • Endoplasmic reticulum
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140.0 - 142.0 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility752.5 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility1.81 g/LALOGPS
logP-1.2ALOGPS
logP-10ChemAxon
logS-2.6ALOGPS
pKa (strongest acidic)1.86ChemAxon
pKa (strongest basic)5ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count15ChemAxon
hydrogen donor count8ChemAxon
polar surface area318.26ChemAxon
rotatable bond count11ChemAxon
refractivity142ChemAxon
polarizability55.86ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Nucleus
  • Endoplasmic reticulum
  • Peroxisome
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location
  • Adrenal Gland
  • Brain
  • Epidermis
  • Fibroblasts
  • Liver
  • Platelet
  • Prostate
  • Skeletal Muscle
Pathways
NameSMPDB LinkKEGG Link
Ammonia RecyclingSMP00009map00910
Carnitine SynthesisSMP00465Not Available
Citric Acid CycleSMP00057map00020
Ethanol DegradationSMP00449Not Available
Folate MetabolismSMP00053map00670
GluconeogenesisSMP00128map00010
Glucose-Alanine CycleSMP00127Not Available
Glutamate MetabolismSMP00072map00250
Glycerol Phosphate ShuttleSMP00124Not Available
Glycerolipid MetabolismSMP00039map00561
Glycine and Serine MetabolismSMP00004map00260
GlycolysisSMP00040map00010
Histidine MetabolismSMP00044map00340
Ketone Body MetabolismSMP00071map00072
Malate-Aspartate ShuttleSMP00129Not Available
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsSMP00482Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty AcidsSMP00481Not Available
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty AcidsSMP00480Not Available
Mitochondrial Electron Transport ChainSMP00355map00190
Nicotinate and Nicotinamide MetabolismSMP00048map00760
Plasmalogen SynthesisSMP00479Not Available
Threonine and 2-Oxobutanoate DegradationSMP00452Not Available
Transfer of Acetyl Groups into MitochondriaSMP00466Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified24.00 (23.00-25.6) uMAdult (>18 years old)BothNormal
Cellular CytoplasmDetected and Quantified88.7 uMAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified29.00 (25.00-33.00) uMAdult (>18 years old)BothPellagra
Associated Disorders and Diseases
Disease References
Pellagra
  • 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
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022309
KNApSAcK IDNot Available
Chemspider ID5682
KEGG Compound IDC00003
BioCyc IDNAD
BiGG ID33480
Wikipedia LinkNAD
NuGOwiki LinkHMDB00902
Metagene LinkHMDB00902
METLIN ID5858
PubChem Compound5893
PDB IDNot Available
ChEBI ID15846
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)Not Available
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. 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(1):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

Only showing the first 50 proteins. There are 261 proteins in total.

Enzymes

Gene Name:
ALDH6A1
Uniprot ID:
Q02252
Reactions
2-Methyl-3-oxopropanoic acid + Coenzyme A + Water + NAD unknown Propionyl-CoA + Carbonic acid + NADHdetails
Malonic semialdehyde + Coenzyme A + NAD unknown Acetyl-CoA + Carbon dioxide + NADH + Hydrogen Iondetails
(S)-Methylmalonic acid semialdehyde + Coenzyme A + NAD unknown Propionyl-CoA + Carbon dioxide + NADH + Hydrogen Iondetails
(S)-Methylmalonic acid semialdehyde + Coenzyme A + NAD unknown Methylmalonyl-CoA + NADH + Hydrogen Iondetails
Gene Name:
DLD
Uniprot ID:
P09622
Reactions
Protein N(6)-(dihydrolipoyl)lysine + NAD unknown protein N(6)-(lipoyl)lysine + NADHdetails
Dihydrolipoamide + NAD unknown Lipoamide + NADH + Hydrogen Iondetails
Dihydrolipoylprotein + NAD unknown Lipoylprotein + NADH + Hydrogen Iondetails
Enzyme N6-(dihydrolipoyl)lysine + NAD unknown Enzyme N6-(lipoyl)lysine + NADH + Hydrogen Iondetails
Gene Name:
AKR1C4
Uniprot ID:
P17516
Reactions
Androsterone + NAD unknown Androstanedione + NADH + Hydrogen Iondetails
Etiocholanolone + NAD unknown Etiocholanedione + NADH + Hydrogen Iondetails
3a,7a-Dihydroxy-5b-cholestane + NAD unknown 7a-Hydroxy-5b-cholestan-3-one + NADH + Hydrogen Iondetails
5-b-Cholestane-3a ,7a ,12a-triol + NAD unknown 7a,12a-Dihydroxy-5b-cholestan-3-one + NADH + Hydrogen Iondetails
Tetrahydrocortisone + NAD unknown 17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + NADH + Hydrogen Iondetails
Tetrahydrocortisol + NAD unknown Dihydrocortisol + NADH + Hydrogen Iondetails
3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al + NAD unknown 11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADH + Hydrogen Iondetails
Tetrahydrocorticosterone + NAD unknown 11b,21-Dihydroxy-5b-pregnane-3,20-dione + NADH + Hydrogen Iondetails
3a,21-Dihydroxy-5b-pregnane-11,20-dione + NAD unknown 21-Hydroxy-5b-pregnane-3,11,20-trione + NADH + Hydrogen Iondetails
3a-Hydroxy-5b-pregnane-20-one + NAD unknown 5a-Pregnane-3,20-dione + NADH + Hydrogen Iondetails
Gene Name:
HPGD
Uniprot ID:
P15428
Reactions
(5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD unknown (5Z,13E)-11-alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADHdetails
Gene Name:
TYR
Uniprot ID:
P14679
Reactions
Tyramine + Oxygen + NADH + Hydrogen Ion unknown Dopamine + NAD + Waterdetails
Gene Name:
AKR1B1
Uniprot ID:
P15121
Reactions
Glycerol + NAD unknown Glyceraldehyde + NADH + Hydrogen Iondetails
Beta-D-Galactose + NADH + Hydrogen Ion unknown Galactitol + NADdetails
L-Arabitol + NAD unknown L-Arabinose + NADH + Hydrogen Iondetails
Lactaldehyde + NAD unknown Pyruvaldehyde + NADH + Hydrogen Iondetails
Gene Name:
ACADS
Uniprot ID:
P16219
Reactions
Butyryl-CoA + NAD unknown (E)-but-2-enoyl-CoA + NADH + Hydrogen Iondetails
Gene Name:
MT-ND1
Uniprot ID:
P03886
Reactions
NADH + Coenzyme Q10 unknown NAD + QH(2)details
Gene Name:
ENPP1
Uniprot ID:
P22413
Reactions
NAD + Water unknown Adenosine monophosphate + beta-nicotinamide D-ribonucleotidedetails
Gene Name:
NDUFS2
Uniprot ID:
O75306
Reactions
NADH + Coenzyme Q10 unknown NAD + QH(2)details
NADH + acceptor unknown NAD + reduced acceptordetails
Gene Name:
CYB5R3
Uniprot ID:
P00387
Reactions
NADH + ferricytochrome b5 unknown NAD + Hydrogen Ion + ferrocytochrome b5details
Gene Name:
MT-ND4L
Uniprot ID:
P03901
Reactions
NADH + Coenzyme Q10 unknown NAD + QH(2)details
Gene Name:
SC5DL
Uniprot ID:
O75845
Reactions
Lathosterol + NADH + Hydrogen Ion + Oxygen unknown 7-Dehydrocholesterol + NAD + Waterdetails
Gene Name:
MT-ND5
Uniprot ID:
P03915
Reactions
NADH + Coenzyme Q10 unknown NAD + QH(2)details
Gene Name:
NDUFS3
Uniprot ID:
O75489
Reactions
NADH + Coenzyme Q10 unknown NAD + QH(2)details
NADH + acceptor unknown NAD + reduced acceptordetails
Gene Name:
NDUFV2
Uniprot ID:
P19404
Reactions
NADH + Coenzyme Q10 unknown NAD + QH(2)details
NADH + acceptor unknown NAD + reduced acceptordetails
Gene Name:
NDUFS8
Uniprot ID:
O00217
Reactions
NADH + Coenzyme Q10 unknown NAD + QH(2)details
NADH + acceptor unknown NAD + reduced acceptordetails
Gene Name:
MT-ND2
Uniprot ID:
P03891
Reactions
NADH + Coenzyme Q10 unknown NAD + QH(2)details
Gene Name:
ALDH4A1
Uniprot ID:
P30038
Reactions
L-Glutamic gamma-semialdehyde + NAD + Water unknown L-Glutamic acid + NADH + Hydrogen Iondetails
1-Pyrroline-5-carboxylic acid + NAD + Water unknown L-Glutamic acid + NADH + Hydrogen Iondetails
Pyrroline hydroxycarboxylic acid + NAD + Water unknown 4-Hydroxy-L-glutamic acid + NADH + Hydrogen Iondetails
4-Hydroxy-L-glutamic acid + NADH + Hydrogen Ion unknown L-4-Hydroxyglutamate semialdehyde + NAD + Waterdetails
Gene Name:
NDUFS1
Uniprot ID:
P28331
Reactions
NADH + Coenzyme Q10 unknown NAD + QH(2)details
NADH + acceptor unknown NAD + reduced acceptordetails
Gene Name:
NDUFAB1
Uniprot ID:
O14561
Gene Name:
MT-ND4
Uniprot ID:
P03905
Reactions
NADH + Coenzyme Q10 unknown NAD + QH(2)details
Gene Name:
NDUFS7
Uniprot ID:
O75251
Reactions
NADH + Coenzyme Q10 unknown NAD + QH(2)details
NADH + acceptor unknown NAD + reduced acceptordetails
Gene Name:
XDH
Uniprot ID:
P47989
Reactions
Hypoxanthine + NAD + Water unknown Xanthine + NADHdetails
Hypoxanthine + NAD + Water unknown Xanthine + NADH + Hydrogen Iondetails
Xanthine + NAD + Water unknown Uric acid + NADH + Hydrogen Iondetails

Only showing the first 50 proteins. There are 261 proteins in total.