Record Information
Version2.0
Creation Date2012-05-31 13:47:00 -0600
Update Date2015-06-03 15:53:49 -0600
Secondary Accession Numbers
  • ECMDB01179
Identification
Name:Nicotinic acid adenine dinucleotide
DescriptionNicotinic 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
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
Weight:Average: 665.4178
Monoisotopic: 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-1λ⁵-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
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
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.88 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity140.17 m³·mol⁻¹ChemAxon
Polarizability58.26 ųChemAxon
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
Adenosine triphosphate + Nicotinic acid adenine dinucleotide + Ammonia > Adenosine monophosphate + Pyrophosphate + NAD
Hydrogen ion + Adenosine triphosphate + Nicotinamide ribotide > Pyrophosphate + Nicotinic acid adenine dinucleotide
Adenosine triphosphate + Nicotinamide ribotide > Pyrophosphate + Nicotinic acid adenine dinucleotide
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
Adenosine triphosphate + Nicotinic acid adenine dinucleotide + Ammonia <> Adenosine monophosphate + Pyrophosphate + NAD
SMPDB Pathways:
NAD biosynthesisPW000829 ThumbThumb?image type=greyscaleThumb?image type=simple
NAD salvagePW000830 ThumbThumb?image type=greyscaleThumb?image type=simple
Nitrogen metabolismPW000755 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1202903000-23becb537df72d0e35b9View in MoNA
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

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the reversible adenylation of nicotinate mononucleotide (NaMN) to nicotinic acid adenine dinucleotide (NaAD)
Gene Name:
nadD
Uniprot ID:
P0A752
Molecular weight:
24528
Reactions
ATP + beta-nicotinate-D-ribonucleotide = diphosphate + deamido-NAD(+).
General function:
Involved in NAD+ synthase (glutamine-hydrolyzing) activity
Specific function:
Catalyzes a key step in NAD biosynthesis, transforming deamido-NAD into NAD by a two-step reaction
Gene Name:
nadE
Uniprot ID:
P18843
Molecular weight:
30637
Reactions
ATP + deamido-NAD(+) + NH(3) = AMP + diphosphate + NAD(+).
General function:
Involved in negative regulation of transcription, DNA-dependent
Specific function:
NadR is bifunctional; it interacts with pnuC at low internal NAD levels, permitting transport of NMN intact into the cell. As NAD levels increase within the cell, the affinity of nadR for the operator regions of nadA, nadB, and pncB increases, repressing the transcription of these genes
Gene Name:
nadR
Uniprot ID:
P27278
Molecular weight:
47346
Reactions
ATP + nicotinamide ribonucleotide = diphosphate + NAD(+).
ATP + N-ribosylnicotinamide = ADP + nicotinamide ribonucleotide.
General function:
Involved in hydrolase activity
Specific function:
NAD(+) + H(2)O = AMP + NMN
Gene Name:
nudC
Uniprot ID:
P32664
Molecular weight:
29689
Reactions
NAD(+) + H(2)O = AMP + NMN.