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Showing Compound adenosine 3',5'-bisphosphate (FDB030650)

Record Information
Version1.0
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
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3'-PhosphoadenylateChEBI
Adenosine 3',5'-bisphosphateChEBI
PAPChEBI
Phosphoadenosine phosphateChEBI
3'-Phosphoadenylic acidGenerator
Adenosine 3',5'-bisphosphoric acidGenerator
Phosphoadenosine phosphoric acidGenerator
Adenosine 3',5'-diphosphoric acidGenerator
3'-Phosphoryl-AMPHMDB
3,5-ADPHMDB
3,5-DiphosphoadenosineHMDB
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
3',5'-ADPHMDB
Adenosine 3'-phosphate-5'-phosphateHMDB
Predicted Properties
PropertyValueSource
Water Solubility3.33 g/LALOGPS
logP-1.6ALOGPS
logP-4.8ChemAxon
logS-2.1ALOGPS
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
BioavailabilityNoChemAxon
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
InChI KeyWHTCPDAXWFLDIH-KQYNXXCUSA-N
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
Classification
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
Substituents
  • 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
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
Spectra
Spectra
EI-MS/GC-MS
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
Predicted GC-MSAdenosine 3',5'-diphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAdenosine 3',5'-diphosphate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAdenosine 3',5'-diphosphate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAdenosine 3',5'-diphosphate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAdenosine 3',5'-diphosphate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAdenosine 3',5'-diphosphate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAdenosine 3',5'-diphosphate, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAdenosine 3',5'-diphosphate, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-000i-0913100000-4559e980fc823f06cda12020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-000i-0910000000-164b37f4075a5627b64d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-000i-1900000000-0f28c9a19c771609202d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-003r-3900000000-fc11f9ff14bc678ffb892021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-057i-2913300000-fdb650a7ed3a1d7dc1192021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0059-9700000000-e0ed082bd1249fa162f62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-a2612ac21c9094d3d4b12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-0900000000-a48b75d77591f32a31a62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-164b37f4075a5627b64d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0913100000-5a86462d5152e2e074f02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0101900000-c682799b7471e544d5a72021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0902300000-77268ef9fe8672f81e9f2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-6986eb10675f363acf422015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-493254661a51349997bd2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-7801900000-b4b0af4deca129a6a12c2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-9800000000-4a1ffcf05d9938fe121e2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-fb4a5bf16d0e5bcaa1e02015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-63709bad7395f9f33acc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900100000-1be0541745ea8310e7172021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-4901000000-46fabb89b3c8f5f65bc82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000900000-e292158e80c5681369df2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0923500000-c2fa14d2158399b30f0c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-1779000000-aed0b018efcf2528cabd2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference