Nicotinic acid adenine dinucleotide (PAMDB000286)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000286
Identification
Name: Nicotinic acid adenine dinucleotide
Description:Nicotinic acid adenine dinucleotide phosphate, (NAADP), is a Ca2+-mobilizing second messenger synthesized in response to extracellular stimuli. NAADP binds to and opens Ca2+ channels on intracellular organelles, thereby increasing the intracellular Ca2+ concentration which, in turn, modulates a variety of cellular processes. Structurally, it is a dinucleotide that only differs from the house-keeping enzyme cofactor, NADP by a hydroxyl group (replacing the nicotinamide amino group) and yet this minor modification converts it into the most potent Ca2+-mobilizing second messenger yet described.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Deamido-NAD
  • Deamido-NAD+
  • Deamido-NAD+
  • Deamidonicotinamide adenine dinucleoetide
  • Deamino-nad+
  • NAAD
  • NaADN
  • NAADP
  • Nicotinate adenine dinucleotide
  • Nicotinate adenine dinucleotide phosphate
  • Nicotinic acid adenine dinucleotide
  • Nicotinic acid adenine dinucleotide phosphate
  • Nicotinic acid adenine dinucleotide phosphoric acid
Chemical Formula: C21H27N6O15P2
Average Molecular Weight: 665.4178
Monoisotopic Molecular Weight: 665.100962248
InChI Key: SENPVEZBRZQVST-HISDBWNOSA-O
InChI: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
CAS number: 6450-77-7
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-carboxy-1???pyridin-1-ylium
Traditional IUPAC Name: deamido-NAD(+)
SMILES:NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)[N+]4=CC=CC(=C4)C(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine nucleotide sugars
Direct Parent Purine nucleotide sugars
Alternative Parents
Substituents
  • Purine nucleotide sugar
  • Purine ribonucleoside diphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Pyridine carboxylic acid or derivatives
  • Pyridine carboxylic acid
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Pyridinium
  • Pyridine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.88 mg/mLALOGPS
logP-0.89ALOGPS
logP-9.9ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area312.47 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity140.17 m3·mol-1ChemAxon
Polarizability58.26 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + Hydrogen ion + Nicotinamide ribotide <> Nicotinic acid adenine dinucleotide + Pyrophosphate
Adenosine triphosphate + Nicotinic acid adenine dinucleotide + Ammonium > Adenosine monophosphate + Hydrogen ion + NAD + Pyrophosphate
Adenosine triphosphate + Nicotinic acid adenine dinucleotide + Ammonia <> Adenosine monophosphate + Pyrophosphate + NAD
Nicotinic acid adenine dinucleotide + Water <> Adenosine monophosphate + Nicotinamide ribotide
Adenosine triphosphate + Nicotinamide ribotide <> Pyrophosphate + Nicotinic acid adenine dinucleotide
Adenosine triphosphate + Nicotinic acid adenine dinucleotide + L-Glutamine + Water > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + NAD + L-Glutamate
nicotinate beta-D-ribonucleotide + Adenosine triphosphate + Hydrogen ion + Nicotinamide ribotide > Pyrophosphate + Nicotinic acid adenine dinucleotide
Nicotinic acid adenine dinucleotide + Water + L-Glutamine + Adenosine triphosphate > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + L-Glutamic acid + NAD + L-Glutamate
Nicotinic acid adenine dinucleotide + Adenosine triphosphate + Ammonium > Hydrogen ion + Adenosine monophosphate + Pyrophosphate + NAD
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-1ae9f4d0896b777b28c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0000009000-f1d50bdee2c40a519304View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9730204000-6e772ef6b1bb54fbe399View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000009000-a61b90d48d56a74bb6c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-0100109000-b0e0147bb3637f905fd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01rt-9300000000-05f34f8e6f2c28916f6dView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID18304
HMDB IDHMDB01179
Pubchem Compound ID165490
Kegg IDC00857
ChemSpider ID145043
WikipediaNAADP
BioCyc IDDEAMIDO-NAD
EcoCyc IDDEAMIDO-NAD
Ligand ExpoNXX