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Record Information
Version1.0
Creation Date2016-09-30 22:19:08 UTC
Update Date2020-05-20 23:11:05 UTC
BMDB IDBMDB0000061
Secondary Accession Numbers
  • BMDB00061
Metabolite Identification
Common NameAdenosine 3',5'-diphosphate
DescriptionAdenosine 3',5'-diphosphate, also known as 3-phosphoadenosine 5-phosphate or 3'-phosphoadenylate, 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. Adenosine 3',5'-diphosphate is a strong basic compound (based on its pKa). Adenosine 3',5'-diphosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC10H15N5O10P2
Average Molecular Weight427.2011
Monoisotopic Molecular Weight427.029414749
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid
Traditional Nameadenosine 3',5'-bisphosphate
CAS Registry Number1053-73-2
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Golgi
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility614.5 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9332100000-c2cf1343058e5c460684View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9141400000-8e8cf251eecd6d39cf02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0902300000-77268ef9fe8672f81e9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-6986eb10675f363acf42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-493254661a51349997bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-7801900000-b4b0af4deca129a6a12cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-9800000000-4a1ffcf05d9938fe121eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-fb4a5bf16d0e5bcaa1e0View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Golgi
  • Mitochondria
Biospecimen Locations
  • Brain
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000061
DrugBank IDDB01812
Phenol Explorer Compound IDNot Available
FooDB IDFDB030650
KNApSAcK IDC00019352
Chemspider ID140102
KEGG Compound IDC00054
BioCyc ID3-5-ADP
BiGG ID33684
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound159296
PDB IDNot Available
ChEBI ID17985
References
Synthesis ReferenceTsunako, Mitsutomo; Kotone, Akira. Preparation of nucleoside-2',5'- and 3',5'-diphosphoric acids. Jpn. Kokai Tokkyo Koho (1991), 13 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in galactosylceramide sulfotransferase activity
Specific function:
Catalyzes the sulfation of membrane glycolipids. Seems to prefer beta-glycosides at the non-reducing termini of sugar chains attached to a lipid moiety. Catalyzes the synthesis of HSO3-3-galactosylceramide (sulfatide), a major lipid component of the myelin sheath and of HSO3-3-monogalactosylalkylacylglycerol (seminolipid), present in spermatocytes. Also acts on lactosylceramide, galactosyl 1-alkyl-2-sn-glycerol and galactosyl diacylglycerol (in vitro) (By similarity).
Gene Name:
GAL3ST1
Uniprot ID:
A6QNK1
Molecular weight:
48754.0
Reactions
Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate → 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphatedetails
Galabiosylceramide (d18:1/22:0) + Phosphoadenosine phosphosulfate → Galabiosylceramide-sulfate + Adenosine 3',5'-diphosphatedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Converts adenosine 3'-phosphate 5'-phosphosulfate (PAPS) to adenosine 5'-phosphosulfate (APS) and 3'(2')-phosphoadenosine 5'- phosphate (PAP) to AMP. Has 1000-fold lower activity towards inositol 1,4-bisphosphate (Ins(1,4)P2) and inositol 1,3,4-trisphosphate (Ins(1,3,4)P3), but does not hydrolyze Ins(1)P, Ins(3,4)P2, Ins(1,3,4,5)P4 or InsP6 (By similarity).
Gene Name:
BPNT1
Uniprot ID:
Q3ZCK3
Molecular weight:
33328.0
General function:
Involved in protein-tyrosine sulfotransferase activity
Specific function:
Catalyzes the O-sulfation of tyrosine residues within acidic motifs of polypeptides, using 3'-phosphoadenylyl sulfate (PAPS) as cosubstrate.
Gene Name:
TPST2
Uniprot ID:
Q3SYY2
Molecular weight:
41967.0
General function:
Involved in aryl sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk (By similarity).
Gene Name:
SULT1A1
Uniprot ID:
P50227
Molecular weight:
34184.0
Reactions
Phosphoadenosine phosphosulfate + Phenol → Adenosine 3',5'-diphosphate + Phenol sulphatedetails
Phosphoadenosine phosphosulfate + Dehydroepiandrosterone → Adenosine 3',5'-diphosphate + DHEA sulfatedetails
General function:
Involved in [heparan sulfate]-glucosamine N-sulfotransf
Specific function:
Essential bifunctional enzyme that catalyzes both the N-deacetylation and the N-sulfation of glucosamine (GlcNAc) of the glycosaminoglycan in heparan sulfate. Modifies the GlcNAc-GlcA disaccharide repeating sugar backbone to make N-sulfated heparosan, a prerequisite substrate for later modifications in heparin biosynthesis. Plays a role in determining the extent and pattern of sulfation of heparan sulfate. Required for the exosomal release of SDCBP, CD63 and syndecan (By similarity).
Gene Name:
NDST2
Uniprot ID:
O97583
Molecular weight:
100897.0
General function:
Involved in estrone sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone (PubMed:1900200) (By similarity). Is a key enzyme in estrogen homeostasis, the sulfation of estrogens leads to their inactivation. Also sulfates dehydroepiandrosterone (DHEA), pregnenolone, (24S)-hydroxycholesterol and xenobiotic compounds like ethinylestradiol, equalenin, diethyl stilbesterol and 1-naphthol at significantly lower efficiency. Does not sulfonate cortisol, testosterone and dopamine (By similarity).
Gene Name:
SULT1E1
Uniprot ID:
P19217
Molecular weight:
34640.0
Reactions
Estrone + Phosphoadenosine phosphosulfate → Estrone sulfate + Adenosine 3',5'-diphosphatedetails