Adenosine-3'-5'-Diphosphate

Identification

Name
Adenosine-3'-5'-Diphosphate
Accession Number
DB01812  (EXPT00370)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
C65F80D52U
CAS number
Not Available
Weight
Average: 427.2011
Monoisotopic: 427.029414749
Chemical Formula
C10H15N5O10P2
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

Pharmacology

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

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0000061
KEGG Compound
C00054
PubChem Compound
159296
PubChem Substance
46507388
ChemSpider
140102
ChEBI
17985
ChEMBL
CHEMBL574817
HET
A3P
PDB Entries
1aqu / 1aqy / 1bo6 / 1cy0 / 1efh / 1fmj / 1fml / 1fth / 1g3m / 1hi4
show 94 more

Clinical Trials

Clinical Trials
Not Available

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-6.1ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.71ChemAxon
pKa (Strongest Basic)4.92ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area232.6 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.94 m3·mol-1ChemAxon
Polarizability34.31 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

Taxonomy

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
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
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
adenosine bisphosphate (CHEBI:17985)

Targets

Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]
Kind
Protein
Organism
Human
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
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
Kind
Protein
Organism
Human
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
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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:06