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Identification
YMDB IDYMDB00360
NameAdenosine diphosphate ribose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAdenosine diphosphate ribose 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. Adenosine diphosphate ribose is a strong basic compound (based on its pKa). Adenosine diphosphate ribose exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
Synonyms
  • (Rib5)ppA
  • [5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [hydroxy-[(3,4,5-trihydroxyoxolan-2-yl)methoxy]phosphoryl] hydrogen phosphate
  • 5-(Adenosine 5'-pyrophosphoryl)-D-ribose
  • A5'pp5Rib
  • Adenosine 5'-diphosphoribose
  • Adenosine diphosphate ribose
  • AdoPPRib
  • ADP Ribose
  • ADP-D-ribose
  • ADP-Rib
  • ADP-ribose
  • ADPribose
  • Ribose adenosine diphosphate
  • Adenosine diphosphoric acid ribose
  • D-Ribofuranos-5-yl-ADP
  • Diphosphate ribose, adenosine
  • 5'-Diphosphoribose, adenosine
  • Adenosine diphosphoribose
  • Diphosphoribose, adenosine
  • Adenosine 5' diphosphoribose
  • Ribose, ADP
  • Ribose, adenosine diphosphate
  • (3E)-3-Penten-2-one
  • (3E)-Pent-3-en-2-one
  • (e)-3-Penten-2-one
  • 2-oxo-3-Pentene
  • 3-Penten-2-one
  • 3-Penten-2-one (methyl vinyl ketone)
  • Ethylidene acetone
  • FEMA no. 3417
  • Methyl 1-propenyl ketone
  • Pent-3-en-2-one
  • 1-Hydroxyoctane
  • 1-Octanol
  • 1-Oktanol
  • Capryl alcohol
  • Caprylic alcohol
  • N-Heptyl carbinol
  • N-Octan-1-ol
  • Primary octyl alcohol
  • 2-Capryl alcohol
  • 2-Octanol
  • 2-Octanol ~99%
  • Alcohol C-8
  • Alfol 8
  • DL-2-Octanol
  • Dytol m-83
  • Emery 3322
  • Emery 3324
  • Epal 8
  • Heptyl carbinol
  • Hexyl methyl carbinol
  • Lorol 20
  • Lorol C8
  • N-Octanol
  • N-Octyl alcohol
  • N-Octyl-alcohol
  • Octan-1-ol
  • Octan-2-ol
  • Octan-2-ol 98+ %
  • Octilin
  • Octyl alcohol
  • Octyl alcohol normal-primary
  • Octyl-alcohol
  • Prim-N-octyl alcohol
  • Sipol L8
  • 1 Octanol
  • N Octanol
  • Alcohol, N-octyl
  • N Octyl alcohol
  • S-Succinyl-dihydrolipoamide
  • S-Succinyldihydrolipoamide
  • Deamido-NAD
  • Deamido-nad+
  • Deamino-nad+
  • Nicotinate adenine dinucleotide
  • Deamidonicotinamide adenine dinucleoetide
  • NAAD
  • NaADN
CAS number20762-30-5
WeightAverage: 559.3157
Monoisotopic: 559.071673493
InChI KeySRNWOUGRCWSEMX-UHFFFAOYSA-N
InChIInChI=1S/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(23)8(21)5(32-14)1-30-35(26,27)34-36(28,29)31-2-6-9(22)11(24)15(25)33-6/h3-6,8-11,14-15,21-25H,1-2H2,(H,26,27)(H,28,29)(H2,16,17,18)
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(3,4,5-trihydroxyoxolan-2-yl)methoxy]phosphoryl}oxy)phosphinic acid
Traditional IUPAC Nameadp ribose
Chemical FormulaC15H23N5O14P2
SMILES[H]OC1([H])OC([H])(C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])C2([H])OC([H])(N3C([H])=NC4=C3N=C([H])N=C4N([H])[H])C([H])(O[H])C2([H])O[H])C([H])(O[H])C1([H])O[H]
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine nucleotide sugars
Direct ParentPurine nucleotide sugars
Alternative Parents
Substituents
  • Purine nucleotide sugar
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidine
  • Alkyl phosphate
  • Imidolactam
  • Phosphoric acid ester
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Hemiacetal
  • Organoheterocyclic compound
  • Polyol
  • Azacycle
  • Oxacycle
  • Organic oxide
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.61 g/LALOGPS
logP-1.8ALOGPS
logP-6.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area291.52 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity111.12 m³·mol⁻¹ChemAxon
Polarizability46.75 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • nucleus
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB ReactionsNot Available
KEGG Reactions
NAD + waterhydron + Niacinamide + Adenosine diphosphate ribose
NAD + waterhydron + Niacinamide + Adenosine diphosphate ribose
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r5-1196680000-fb6c20cc4fb54b50028eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01r5-2115904000-4597a65923641317c791JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0910130000-b9073b1bbcee0d4c7c6eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-4407a7719b31b18bb57bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-9d6c2b567f9da9d1d1ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-1701390000-e958d4521e35989750e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1910100000-a653cbe7cba6b5fab234JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-3900000000-c8a10ccf06e1cb8b548aJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16960
HMDB IDHMDB01178
Pubchem Compound ID192
Kegg IDC00301
ChemSpider ID187
FOODB IDFDB022468
WikipediaAdenosine_diphosphate_ribose
BioCyc IDADENOSINE_DIPHOSPHATE_RIBOSE

Enzymes

General function:
Involved in phosphatase activity
Specific function:
Highly specific phosphatase involved in the metabolism of ADP-ribose 1''-phosphate (Appr1p) which is produced as a consequence of tRNA splicing
Gene Name:
POA1
Uniprot ID:
P38218
Molecular weight:
19937.59961
Reactions
ADP-ribose 1''-phosphate + H(2)O → ADP-ribose + phosphate.
General function:
Involved in phosphatase activity
Specific function:
Highly specific phosphatase involved in the metabolism of ADP-ribose 1''-phosphate (Appr1p) which is produced as a consequence of tRNA splicing
Gene Name:
Not Available
Uniprot ID:
Q04299
Molecular weight:
32067.0
Reactions
ADP-ribose 1''-phosphate + H(2)O → ADP-ribose + phosphate.
General function:
Involved in hydrolase activity
Specific function:
ADP-ribose + H(2)O = AMP + D-ribose 5- phosphate
Gene Name:
YSA1
Uniprot ID:
Q01976
Molecular weight:
26086.80078
Reactions
ADP-ribose + H(2)O → AMP + D-ribose 5-phosphate.