Human Metabolome Database Version 3.5

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Showing metabocard for NAD (HMDB00902)

enzymes (261)

Blood
Urine

Record Information

Version

3.5

Creation Date

2005-11-16 08:48:42 -0700

Update Date

2013-02-08 17:09:33 -0700

HMDB ID

HMDB00902

Secondary Accession Numbers

None

Metabolite Identification

Common Name

NAD

Description

NAD (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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

3-Carbamoyl-1-beta-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt
3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt
3-Carbamoyl-1-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate
3-Carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate
Adenine-nicotinamide dinucleotide
beta-Diphosphopyridine nucleotide
beta-NAD
beta-Nicotinamide adenine dinucleotide
beta-Nicotinamide adenine dinucleotide trihydrate
CO-I
Codehydrase I
Codehydrogenase I
Coenzyme I
Cozymase
Cozymase I
Diphosphopyridine nucleotide
Diphosphopyridine nucleotide oxidized
Endopride
NAD trihydrate
NAD-oxidized
Nicotinamide adenine dinucleotide
Nicotinamide adenine dinucleotide oxidized
Nicotinamide dinucleotide
Nicotineamide adenine dinucleotide
Oxidized diphosphopyridine nucleotide
Pyridine nucleotide diphosphate
[(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
[adenylate-32-P]-NAD

Chemical Formula

C₂₁H₂₈N₇O₁₄P₂

Average Molecular Weight

664.433

Monoisotopic Molecular Weight

664.116946663

IUPAC Name

1-[(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 Name

1-[(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 Number

53-84-9

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 Key

BAWFJGJZGIEFAR-NNYOXOHSSA-O

Chemical Taxonomy

Kingdom

Organic Compounds

Super Class

Nucleosides, Nucleotides, and Analogues

Class

Purine Nucleotides

Sub Class

Purine 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 Parent

Purine Ribonucleoside Diphosphates

Ontology

Status

Detected 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

Application

Not Available

Cellular locations

Extracellular
Mitochondria
Nucleus
Endoplasmic reticulum
Peroxisome

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	140.0 - 142.0 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	752.5 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.81 g/L	ALOGPS
LogP	-1.18	ALOGPS
LogP	-10	ChemAxon
LogS	-2.59	ALOGPS
pKa (strongest acidic)	1.86	ChemAxon
pKa (strongest basic)	5	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	318.26 A²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	142	ChemAxon
Polarizability	55.86	ChemAxon
Formal Charge	1	ChemAxon
Physiological Charge	-1	ChemAxon

Spectra

1H NMR Spectrum

MS/MS Spectrum Quattro_QQQ 10

MS/MS Spectrum Quattro_QQQ 25

MS/MS Spectrum Quattro_QQQ 40

MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)

[1H,1H] 2D NMR Spectrum

[1H,13C] 2D NMR Spectrum

Biological Properties

Cellular Locations

Extracellular
Mitochondria
Nucleus
Endoplasmic reticulum
Peroxisome

Biofluid Locations

Blood
Cellular Cytoplasm

Tissue Location

Skeletal Muscle
Fibroblasts
Liver
Epidermis
Brain
Prostate
Adrenal Gland
Platelet

Pathways

Name	SMPDB Link	KEGG Link
Ammonia Recycling	SMP00009	map00910
Glycolysis	SMP00040	map00010
Citric Acid Cycle	SMP00057	map00020
Gluconeogenesis	SMP00128	map00010
Glutamate Metabolism	SMP00072	map00250
Glycerol Phosphate Shuttle	SMP00124	Not Available
Glucose-Alanine Cycle	SMP00127	Not Available
Nicotinate and Nicotinamide Metabolism	SMP00048	map00760
Mitochondrial Electron Transport Chain	SMP00355	map00190
Ketone Body Metabolism	SMP00071	map00072
Histidine Metabolism	SMP00044	map00340
Malate-Aspartate Shuttle	SMP00129	Not Available
Glycerolipid Metabolism	SMP00039	map00561
Ethanol Degradation	SMP00449	Not Available
Threonine and 2-Oxobutanoate Degradation	SMP00452	Not Available
Carnitine Synthesis	SMP00465	Not Available
Transfer of Acetyl Groups into Mitochondria	SMP00466	Not Available
Plasmalogen Synthesis	SMP00479	Not Available
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids	SMP00480	Not Available
Glycine and Serine Metabolism	SMP00004	map00260
Folate Metabolism	SMP00053	map00670
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids	SMP00482	Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids	SMP00481	Not Available

Normal Concentrations

Biofluid	Status		Value	Age	Sex	Condition	Reference
Blood	Detected and Quantified		24.00 (23.00-25.6) uM	Adult (>18 years old)	Both	Normal	17709435
Cellular Cytoplasm	Detected and Quantified		88.7 uM	Adult (>18 years old)	Both	Normal	15882454

Abnormal Concentrations

Biofluid	Status		Value	Age	Sex	Condition	Reference
Blood	Detected and Quantified		29.00 (25.00-33.00) uM	Adult (>18 years old)	Both	Pellagra	17709435

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 IDs

None

External Links

DrugBank ID

Not Available

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

FDB022309

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

NuGOwiki Link

Metagene Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15846

References

Synthesis Reference

Hughes, 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

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
Ying W: NAD+ and NADH in cellular functions and cell death. Front Biosci. 2006 Sep 1;11:3129-48. Pubmed: 16720381
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
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
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
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
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
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
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
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
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

Enzymes

Name:	Pyruvate dehydrogenase E1 component subunit beta, mitochondrial
Reactions:	Not Available
Gene Name:	PDHB
Uniprot ID:	P11177
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial
Reactions:	Not Available
Gene Name:	PDHA1
Uniprot ID:	P08559
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:	Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial
Reactions:	Not Available
Gene Name:	PDHA2
Uniprot ID:	P29803
Protein Sequence:	FASTA
Gene Sequence:	FASTA

Name:

Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial

Reactions:

2-Methyl-3-oxopropanoic acid + Coenzyme A + Water + NAD unknown Propionyl-CoA + Carbonic acid + NADH	details
Malonic semialdehyde + Coenzyme A + NAD unknown Acetyl-CoA + Carbon dioxide + NADH + Hydrogen Ion	details
(S)-Methylmalonic acid semialdehyde + Coenzyme A + NAD unknown Propionyl-CoA + Carbon dioxide + NADH + Hydrogen Ion	details
(S)-Methylmalonic acid semialdehyde + Coenzyme A + NAD unknown Methylmalonyl-CoA + NADH + Hydrogen Ion	details

Gene Name:

ALDH6A1

Uniprot ID:

Q02252

Protein Sequence: