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Record Information
Version1.0
Creation Date2016-09-30 22:42:07 UTC
Update Date2020-05-21 16:27:09 UTC
BMDB IDBMDB0001179
Secondary Accession Numbers
  • BMDB01179
Metabolite Identification
Common NameNicotinic acid adenine dinucleotide
DescriptionNicotinic acid adenine dinucleotide, also known as deamido-nad or NAAD, 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. Nicotinic acid adenine dinucleotide is a strong basic compound (based on its pKa). Nicotinic acid adenine dinucleotide exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
Deamido-NADChEBI
Deamido-nad+ChEBI
Deamino-nad+ChEBI
Nicotinate adenine dinucleotideGenerator
Deamidonicotinamide adenine dinucleoetideHMDB
NAADHMDB
NaADNHMDB
Adenine-nicotinic acid dinucleotideHMDB
Deamidodiphosphopyridine nucleotideHMDB
Desamido NADHMDB
Nicotinic acid-adenine dinucleotideHMDB
Chemical FormulaC21H27N6O15P2
Average Molecular Weight665.4178
Monoisotopic Molecular Weight665.100962248
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number6450-77-7
SMILESNot Available
InChI Identifier
InChI=1S/C21H26N6O15P2/c22-17-12-18(24-7-23-17)27(8-25-12)20-16(31)14(29)11(41-20)6-39-44(36,37)42-43(34,35)38-5-10-13(28)15(30)19(40-10)26-3-1-2-9(4-26)21(32)33/h1-4,7-8,10-11,13-16,19-20,28-31H,5-6H2,(H4-,22,23,24,32,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,19-,20-/m1/s1
InChI KeySENPVEZBRZQVST-HISDBWNOSA-O
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
  • Nicotinic-acid-nucleotide
  • Pyridine nucleotide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Pyridine carboxylic acid or derivatives
  • Pyridine carboxylic acid
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyridinium
  • Pyridine
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Monosaccharide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Vinylogous amide
  • Amino acid
  • Secondary alcohol
  • Amino acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Alcohol
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001179
DrugBank IDDB04099
Phenol Explorer Compound IDNot Available
FooDB IDFDB031057
KNApSAcK IDNot Available
Chemspider ID145043
KEGG Compound IDC00857
BioCyc IDDEAMIDO-NAD
BiGG ID36219
Wikipedia LinkNot Available
METLIN ID4234
PubChem Compound165491
PDB IDNot Available
ChEBI ID18304
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Coenzyme transport and metabolism
Specific function:
Nicotinamide/nicotinate-nucleotide adenylyltransferase that acts as an axon maintenance factor (By similarity). Catalyzes the formation of NAD(+) from nicotinamide mononucleotide (NMN) and ATP. Can also use the deamidated form; nicotinic acid mononucleotide (NaMN) as substrate but with a lower efficiency. Cannot use triazofurin monophosphate (TrMP) as substrate. Also catalyzes the reverse reaction, i.e. the pyrophosphorolytic cleavage of NAD(+). For the pyrophosphorolytic activity prefers NAD(+), NADH and NaAD as substrates and degrades nicotinic acid adenine dinucleotide phosphate (NHD) less effectively. Fails to cleave phosphorylated dinucleotides NADP(+), NADPH and NaADP(+) (By similarity). Axon survival factor required for the maintenance of healthy axons: acts by delaying Wallerian axon degeneration, an evolutionarily conserved process that drives the loss of damaged axons (By similarity).
Gene Name:
NMNAT2
Uniprot ID:
Q0VC59
Molecular weight:
34468.0
Reactions
Nicotinic acid mononucleotide + Adenosine triphosphate → Nicotinic acid adenine dinucleotide + Pyrophosphatedetails
General function:
Replication, recombination and repair
Specific function:
Hydrolyzes NAD(P)H to NMNH and AMP (2',5'-ADP), and diadenosine diphosphate to AMP. Has also activity towards NAD(P)(+), ADP-ribose and diadenosine triphosphate. May act to regulate the concentration of peroxisomal nicotinamide nucleotide cofactors required for oxidative metabolism in this organelle.
Gene Name:
NUDT12
Uniprot ID:
Q29RH3
Molecular weight:
50119.0
Reactions
Nicotinic acid adenine dinucleotide + Water → Nicotinic acid mononucleotide + Adenosine monophosphatedetails
Nicotinic acid adenine dinucleotide + Water →2 Nicotinic acid mononucleotidedetails
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the ATP-dependent amidation of deamido-NAD to form NAD. Uses L-glutamine as a nitrogen source.
Gene Name:
NADSYN1
Uniprot ID:
Q3ZBF0
Molecular weight:
79400.0
Reactions
Nicotinic acid adenine dinucleotide + Adenosine triphosphate + Water + L-Glutamine → NAD + Adenosine monophosphate + Pyrophosphate + L-Glutamic aciddetails