NAV

Adenosine 3',5'-diphosphate

Identification

Generic Name
Adenosine 3',5'-diphosphate
DrugBank Accession Number
DB01812
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 427.2011
Monoisotopic: 427.029414749
Chemical Formula
C10H15N5O10P2
Synonyms
  • 3'-Phosphoadenosine 5'-phosphate
  • 3',5'-ADP
  • Adenosine 3'-phosphate-5'-phosphate
  • Adenosine 3',5'-bismonophosphate
  • Phosphoadenosine phosphate

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHeparan sulfate glucosamine 3-O-sulfotransferase 1Not AvailableHumans
USulfotransferase family cytosolic 2B member 1Not AvailableHumans
UNon-secretory ribonucleaseNot AvailableHumans
USulfotransferase 1A1Not AvailableHumans
UHeparan sulfate glucosamine 3-O-sulfotransferase 3A1Not AvailableHumans
URibonuclease pancreaticNot AvailableHumans
UBile salt sulfotransferaseNot AvailableHumans
UEstrogen sulfotransferaseNot AvailableHumans
UDNA topoisomerase 1Not AvailableEscherichia coli (strain K12)
UBifunctional heparan sulfate N-deacetylase/N-sulfotransferase 1Not AvailableHumans
UHolo-[acyl-carrier-protein] synthaseNot AvailableStreptococcus pneumoniae (strain ATCC BAA-255 / R6)
USulfotransferase family cytosolic 1B member 1Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside 3',5'-bisphosphates
Alternative Parents
Purine ribonucleoside monophosphates / Ribonucleoside 3'-phosphates / Pentose phosphates / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Aminopyrimidines and derivatives / Monoalkyl phosphates / Imidolactams / N-substituted imidazoles
show 9 more
Substituents
6-aminopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
adenosine bisphosphate (CHEBI:17985)
Affected organisms
Not Available

Chemical Identifiers

UNII
C65F80D52U
CAS number
1053-73-2
InChI Key
WHTCPDAXWFLDIH-KQYNXXCUSA-N
InChI
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
IUPAC Name
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O

References

General References
Not Available
Human Metabolome Database
HMDB0000061
KEGG Compound
C00054
PubChem Compound
159296
PubChem Substance
46507388
ChemSpider
140102
ChEBI
17985
ChEMBL
CHEMBL574817
ZINC
ZINC000004228234
PDBe Ligand
A3P
PDB Entries
1aqu / 1aqy / 1bo6 / 1cy0 / 1efh / 1fmj / 1fml / 1fth / 1g3m / 1hi4 …
show 110 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.33 mg/mLALOGPS
logP-1.6ALOGPS
logP-5.2Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.4Chemaxon
pKa (Strongest Basic)4.86Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area232.6 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity84.94 m3·mol-1Chemaxon
Polarizability34.28 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5527
Blood Brain Barrier+0.9522
Caco-2 permeable-0.7524
P-glycoprotein substrateNon-substrate0.7216
P-glycoprotein inhibitor INon-inhibitor0.888
P-glycoprotein inhibitor IINon-inhibitor0.9282
Renal organic cation transporterNon-inhibitor0.9411
CYP450 2C9 substrateNon-substrate0.847
CYP450 2D6 substrateNon-substrate0.845
CYP450 3A4 substrateNon-substrate0.5726
CYP450 1A2 substrateNon-inhibitor0.9157
CYP450 2C9 inhibitorNon-inhibitor0.9329
CYP450 2D6 inhibitorNon-inhibitor0.9113
CYP450 2C19 inhibitorNon-inhibitor0.9311
CYP450 3A4 inhibitorNon-inhibitor0.9247
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.966
Ames testNon AMES toxic0.8296
CarcinogenicityNon-carcinogens0.9116
BiodegradationNot ready biodegradable0.9752
Rat acute toxicity2.2659 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9736
hERG inhibition (predictor II)Non-inhibitor0.8816
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0902300000-77268ef9fe8672f81e9f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-6986eb10675f363acf42
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1900000000-493254661a51349997bd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-7801900000-b4b0af4deca129a6a12c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0059-9800000000-4a1ffcf05d9938fe121e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9200000000-fb4a5bf16d0e5bcaa1e0
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

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Details1. Heparan sulfate glucosamine 3-O-sulfotransferase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to position 3 of glucosamine residues in heparan. Catalyzes the rate limiting step in ...
Gene Name
HS3ST1
Uniprot ID
O14792
Uniprot Name
Heparan sulfate glucosamine 3-O-sulfotransferase 1
Molecular Weight
35772.77 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details2. Sulfotransferase family cytosolic 2B member 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Steroid sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulf...
Gene Name
SULT2B1
Uniprot ID
O00204
Uniprot Name
Sulfotransferase family cytosolic 2B member 1
Molecular Weight
41307.32 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details3. Non-secretory ribonuclease
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ribonuclease activity
Specific Function
This is a non-secretory ribonuclease. It is a pyrimidine specific nuclease with a slight preference for U. Cytotoxin and helminthotoxin. Selectively chemotactic for dendritic cells. Possesses a wid...
Gene Name
RNASE2
Uniprot ID
P10153
Uniprot Name
Non-secretory ribonuclease
Molecular Weight
18354.09 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details4. Sulfotransferase 1A1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
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 estroge...
Gene Name
SULT1A1
Uniprot ID
P50225
Uniprot Name
Sulfotransferase 1A1
Molecular Weight
34165.13 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details5. Heparan sulfate glucosamine 3-O-sulfotransferase 3A1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to an N-unsubstituted glucosamine linked to a 2-O-sulfo iduronic acid unit on heparan ...
Gene Name
HS3ST3A1
Uniprot ID
Q9Y663
Uniprot Name
Heparan sulfate glucosamine 3-O-sulfotransferase 3A1
Molecular Weight
44899.155 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details6. Ribonuclease pancreatic
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ribonuclease a activity
Specific Function
Endonuclease that catalyzes the cleavage of RNA on the 3' side of pyrimidine nucleotides. Acts on single-stranded and double-stranded RNA.
Gene Name
RNASE1
Uniprot ID
P07998
Uniprot Name
Ribonuclease pancreatic
Molecular Weight
17644.125 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details7. Bile salt sulfotransferase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name
SULT2A1
Uniprot ID
Q06520
Uniprot Name
Bile salt sulfotransferase
Molecular Weight
33779.57 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details8. Estrogen sulfotransferase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
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. May play a role in the regulation of estrogen r...
Gene Name
SULT1E1
Uniprot ID
P49888
Uniprot Name
Estrogen sulfotransferase
Molecular Weight
35126.185 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details9. DNA topoisomerase 1
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Releases the supercoiling and torsional tension of DNA, which is introduced during the DNA replication and transcription, by transiently cleaving and rejoining one strand of the DNA duplex. Introdu...
Gene Name
topA
Uniprot ID
P06612
Uniprot Name
DNA topoisomerase 1
Molecular Weight
97349.0 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details10. Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Deacetylase activity
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 ...
Gene Name
NDST1
Uniprot ID
P52848
Uniprot Name
Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 1
Molecular Weight
100867.015 Da
Details11. Holo-[acyl-carrier-protein] synthase
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Transfers the 4'-phosphopantetheine moiety from coenzyme A to a Ser of acyl-carrier-protein.
Gene Name
acpS
Uniprot ID
P0A2W7
Uniprot Name
Holo-[acyl-carrier-protein] synthase
Molecular Weight
13388.005 Da
Details12. Sulfotransferase family cytosolic 1B member 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulf...
Gene Name
SULT1B1
Uniprot ID
O43704
Uniprot Name
Sulfotransferase family cytosolic 1B member 1
Molecular Weight
34898.955 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52