Details of the Drug

General Information of Drug (ID: DMOB7P6)

Drug Name
2',3'-ddATP
Synonyms
2',3'-Dideoxyadenosine triphosphate; ddATP; UNII-9MCI2H1EJ6; 2',3'-dideoxyadenosine-5'-triphosphate; 24027-80-3; dideoxyadenosine triphosphate; CHEMBL1383; 9MCI2H1EJ6; 2',3'-DIDEOXYADENOSINE 5'-TRIPHOSPHATE; Adenosine 5'-(tetrahydrogen triphosphate), 2',3'-dideoxy-; 2',3'-Dideoxy-ATP; ddA-TP; ATP,2',3'-dideoxy; SCHEMBL79815; GTPL1709; AC1L230G; DTXSID90178767; MolPort-044-561-436; ZINC12501706; BDBM50164644; AKOS030589611; 2'',3''-dideoxyadenosine triphosphate; DB02189; 2',3'-Dideoxyadenosine-5-triphosphate; 2',3'-Dideoxyadenosine Triphosphate (Ddatp)
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 475.18
Topological Polar Surface Area (xlogp) -3.5
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 15
Chemical Identifiers
Formula
C10H16N5O11P3
IUPAC Name
[[(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
Canonical SMILES
C1C[C@@H](O[C@@H]1COP(=O)(O)OP(=O)(O)OP(=O)(O)O)N2C=NC3=C(N=CN=C32)N
InChI
InChI=1S/C10H16N5O11P3/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(24-7)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h4-7H,1-3H2,(H,19,20)(H,21,22)(H2,11,12,13)(H2,16,17,18)/t6-,7+/m0/s1
InChIKey
OAKPWEUQDVLTCN-NKWVEPMBSA-N
Cross-matching ID
PubChem CID
65304
CAS Number
24027-80-3
DrugBank ID
DB02189
TTD ID
D0BK8V

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human immunodeficiency virus Reverse transcriptase (HIV RT) TT84ETX POL_HV1B1 Inhibitor [2]
P2Y purinoceptor 1 (P2RY1) TTA93TL P2RY1_HUMAN Agonist [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1709).
2 Synthesis of 2',3'-dideoxynucleoside 5'-alpha-P-borano-beta,gamma-(difluoromethylene)triphosphates and their inhibition of HIV-1 reverse transcript... J Med Chem. 2005 Apr 7;48(7):2695-700.
3 An examination of deoxyadenosine 5'(alpha-thio)triphosphate as a ligand to define P2Y receptors and its selectivity as a low potency partial agonist of the P2Y1 receptor. Br J Pharmacol. 1997 May;121(2):338-44.
4 Antiviral drugs in current clinical use. J Clin Virol. 2004 Jun;30(2):115-33.
5 HIV-1 reverse transcriptase complex with DNA and nevirapine reveals non-nucleoside inhibition mechanism.Nat Struct Mol Biol.2012 Jan 22;19(2):253-9.
6 A peptide inhibitor of HIV-1 reverse transcriptase using alpha,beta-dehydro residues: a structure-based computer model. J Biomol Struct Dyn. 1998 Oct;16(2):347-54.
7 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
8 Quadruple nucleos(t)ide reverse transcriptase inhibitors-only regimen of tenofovir plus zidovudine/lamivudine/abacavir in heavily pre-treated HIV-1 infected patients: salvage therapy or backbone only Curr HIV Res. 2009 May;7(3):320-6.
9 Emerging antiviral drugs. Expert Opin Emerg Drugs. 2008 Sep;13(3):393-416.
10 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
11 Quantitation of the P2Y(1) receptor with a high affinity radiolabeled antagonist. Mol Pharmacol. 2002 Nov;62(5):1249-57.
12 Molecular cloning of the platelet P2T(AC) ADP receptor: pharmacological comparison with another ADP receptor, the P2Y(1) receptor. Mol Pharmacol. 2001 Sep;60(3):432-9.
13 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 323).
14 Antiaggregatory activity in human platelets of potent antagonists of the P2Y 1 receptor. Biochem Pharmacol. 2004 Nov 15;68(10):1995-2002.
15 2-Substitution of adenine nucleotide analogues containing a bicyclo[3.1.0]hexane ring system locked in a northern conformation: enhanced potency as P2Y1 receptor antagonists. J Med Chem. 2003 Nov 6;46(23):4974-87.
16 2,2'-Pyridylisatogen tosylate antagonizes P2Y1 receptor signaling without affecting nucleotide binding. Biochem Pharmacol. 2004 Jul 15;68(2):231-7.
17 Two disparate ligand-binding sites in the human P2Y1 receptor. Nature. 2015 Apr 16;520(7547):317-21.