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Identification
YMDB IDYMDB00306
Namedeamido-NAD(+)
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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
  • Deamido-NAD
  • deamido-nad+
  • Deamino-NAD+
  • Nicotinate adenine dinucleotide
  • Deamidonicotinamide adenine dinucleoetide
  • NAAD
  • NaADN
CAS numberNot Available
WeightAverage: 665.4178
Monoisotopic: 665.100962248
InChI KeySENPVEZBRZQVST-HISDBWNOSA-O
InChIInChI=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
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-carboxy-1λ⁵-pyridin-1-ylium
Traditional IUPAC Namedeamido-NAD(+)
Chemical FormulaC21H27N6O15P2
SMILESNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)[N+]2=CC(=CC=C2)C(O)=O)[C@@H](O)[C@H]1O
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
StateNot Available
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
  • mitochondrion
  • nucleus
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
NAD metabolismPW002421 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Nicotinate and nicotinamide metabolismec00760 Map00760
SMPDB Reactions
Nicotinic acid mononucleotide + hydron + Adenosine triphosphatedeamido-NAD(+) + Pyrophosphate
Adenosine triphosphate + deamido-NAD(+) + water + L-GlutamineNAD + hydron + Adenosine monophosphate + Pyrophosphate + L-Glutamic acid
KEGG Reactions
Adenosine triphosphate + Ammonium + deamido-NAD(+)Adenosine monophosphate + Pyrophosphate + NAD + hydron
Adenosine triphosphate + hydron + Nicotinic acid mononucleotidePyrophosphate + deamido-NAD(+)
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1202903000-23becb537df72d0e35b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-1ae9f4d0896b777b28c3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0000009000-f1d50bdee2c40a519304JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9730204000-6e772ef6b1bb54fbe399JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000009000-a61b90d48d56a74bb6c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-0100109000-b0e0147bb3637f905fd9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01rt-9300000000-05f34f8e6f2c28916f6dJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Magni, G., Amici, A., Emanuelli, M., Orsomando, G., Raffaelli, N., Ruggieri, S. (2004). "Structure and function of nicotinamide mononucleotide adenylyltransferase." Curr Med Chem 11:873-885.15078171
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18304
HMDB IDHMDB0001179
Pubchem Compound ID45266646
Kegg IDC00857
ChemSpider ID24785634
FOODB IDFDB022469
Wikipedia IDNot Available
BioCyc IDDEAMIDO-NAD

Enzymes

General function:
Involved in NAD+ synthase (glutamine-hydrolyzing) activity
Specific function:
ATP + deamido-NAD(+) + L-glutamine + H(2)O = AMP + diphosphate + NAD(+) + L-glutamate
Gene Name:
QNS1
Uniprot ID:
P38795
Molecular weight:
80684.89844
Reactions
ATP + deamido-NAD(+) + L-glutamine + H(2)O → AMP + diphosphate + NAD(+) + L-glutamate.
General function:
Involved in nucleotidyltransferase activity
Specific function:
ATP + nicotinamide ribonucleotide = diphosphate + NAD(+);ATP + nicotinate ribonucleotide = diphosphate + deamido-NAD+
Gene Name:
NMA2
Uniprot ID:
P53204
Molecular weight:
44908.69922
Reactions
ATP + nicotinamide ribonucleotide → diphosphate + NAD(+).
ATP + nicotinate ribonucleotide → diphosphate + deamido-NAD+
General function:
Involved in nucleotidyltransferase activity
Specific function:
ATP + nicotinamide ribonucleotide = diphosphate + NAD(+)
Gene Name:
NMA1
Uniprot ID:
Q06178
Molecular weight:
45858.60156
Reactions
ATP + nicotinamide ribonucleotide → diphosphate + NAD(+).

Transporters

General function:
Involved in binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P40556
Molecular weight:
41954.0