Record Information
Creation date2015-05-07 19:42:37 UTC
Update date2019-11-26 03:21:51 UTC
Primary IDFDB030650
Secondary Accession Numbers
  • FDB021887
Chemical Information
FooDB Nameadenosine 3',5'-bisphosphate
DescriptionAdenosine-3'-5'-diphosphate, also known as 3'-phosphoadenylate or pap, is a member of the class of compounds known as purine ribonucleoside 3',5'-bisphosphates. Purine ribonucleoside 3',5'-bisphosphates are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. Adenosine-3'-5'-diphosphate is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Adenosine-3'-5'-diphosphate can be found in a number of food items such as beech nut, canola, chickpea, and red algae, which makes adenosine-3'-5'-diphosphate a potential biomarker for the consumption of these food products. Adenosine-3'-5'-diphosphate can be found primarily in cellular cytoplasm, as well as in human brain and liver tissues. Adenosine-3'-5'-diphosphate exists in all living species, ranging from bacteria to humans. In humans, adenosine-3'-5'-diphosphate is involved in several metabolic pathways, some of which include acetaminophen metabolism pathway, tamoxifen action pathway, androgen and estrogen metabolism, and metachromatic leukodystrophy (MLD). Adenosine-3'-5'-diphosphate is also involved in several metabolic disorders, some of which include gaucher disease, krabbe disease, fabry disease, and 17-beta hydroxysteroid dehydrogenase III deficiency.
CAS Number1053-73-2
Adenosine 3',5'-bisphosphateChEBI
Phosphoadenosine phosphateChEBI
3'-Phosphoadenylic acidGenerator
Adenosine 3',5'-bisphosphoric acidGenerator
Phosphoadenosine phosphoric acidGenerator
Adenosine 3',5'-diphosphoric acidGenerator
3-Phosphoadenosine 5-phosphateHMDB
5-(Dihydrogen phosphate) 3-adenylateHMDB
5-(Dihydrogen phosphate)3'-adenylic acidHMDB
Adenosine 3,5-bisHMDB
Adenosine 3,5-bisphosphateHMDB
Adenosine 3'-phosphate-5'-phosphate, disodium saltHMDB
3'-Phosphoadenosine 5'-phosphateHMDB
Adenosine 3'-phosphate-5'-phosphate, monosodium saltHMDB
Adenosine 3'-phosphate-5'-phosphateHMDB
Predicted Properties
Water Solubility3.33 g/LALOGPS
pKa (Strongest Acidic)0.7ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area232.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.94 m³·mol⁻¹ChemAxon
Polarizability34.28 ųChemAxon
Number of Rings3ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H15N5O10P2
IUPAC name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid
InChI IdentifierInChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1
Isomeric SMILESNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O
Average Molecular Weight427.2011
Monoisotopic Molecular Weight427.029414749
Description Belongs to the class of organic compounds known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside 3',5'-bisphosphates
Alternative Parents
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Phosphoric acid ester
  • Monosaccharide
  • Imidolactam
  • Pyrimidine
  • Alkyl phosphate
  • Imidazole
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Route of exposure:


Biological location:


Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
TypeDescriptionSplash KeyView
Predicted GC-MSAdenosine 3',5'-diphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9332100000-c2cf1343058e5c460684Spectrum
Predicted GC-MSAdenosine 3',5'-diphosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9141400000-8e8cf251eecd6d39cf02Spectrum
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-000i-0913100000-4559e980fc823f06cda1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-000i-0910000000-164b37f4075a5627b64dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-000i-1900000000-0f28c9a19c771609202dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0902300000-77268ef9fe8672f81e9fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-6986eb10675f363acf42Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-493254661a51349997bdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-7801900000-b4b0af4deca129a6a12cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-9800000000-4a1ffcf05d9938fe121eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-fb4a5bf16d0e5bcaa1e0Spectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference