Details of the Drug

General Information of Drug (ID: DMD6AJO)

Drug Name
N6-CYCLOPENTYLADENOSINE
Synonyms
N6-Cyclopentyladenosine; 41552-82-3; n-cyclopentyladenosine; (2R,3R,4S,5R)-2-(6-(Cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol; Cyclopentyladenosine; CHEMBL68738; MLS000028368; N(6)-Cyclopentyladenosine; SMR000058639; (2R,3R,4S,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol; Adenosine, N-cyclopentyl-; UNII-7LG47VG1ID; 7LG47VG1ID; N6-CyclopentylAdo; n-cyclopentyl-adenosine; n6-cyclopentyl-adenosine; AC1LCWG1; Opera_ID_1056; GTPL380; MLS002153196; MLS001077332; SCHEMBL120481
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 335.36
Logarithm of the Partition Coefficient (xlogp) 0.9
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 8
Chemical Identifiers
Formula
C15H21N5O4
IUPAC Name
(2R,3R,4S,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
Canonical SMILES
C1CCC(C1)NC2=C3C(=NC=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O
InChI
InChI=1S/C15H21N5O4/c21-5-9-11(22)12(23)15(24-9)20-7-18-10-13(16-6-17-14(10)20)19-8-3-1-2-4-8/h6-9,11-12,15,21-23H,1-5H2,(H,16,17,19)/t9-,11-,12-,15-/m1/s1
InChIKey
SQMWSBKSHWARHU-SDBHATRESA-N
Cross-matching ID
PubChem CID
657378
ChEBI ID
CHEMBL68738
CAS Number
41552-82-3
TTD ID
D03RFA
VARIDT ID
DR00860
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adenosine A1 receptor (ADORA1) TTK25J1 AA1R_HUMAN Inhibitor [2]
Adenosine A2a receptor (ADORA2A) TTM2AOE AA2AR_HUMAN Inhibitor [3]
Adenosine A2b receptor (ADORA2B) TTNE7KG AA2BR_HUMAN Inhibitor [4]
Adenosine A3 receptor (ADORA3) TTJFY5U AA3R_HUMAN Inhibitor [5]
Adenylate cyclase (ADCY) TT2QM9D NOUNIPROTAC Inhibitor [6]
Solute carrier family 29 member 1 (SLC29A1) TTLXAKE S29A1_HUMAN Inhibitor [7]
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: 380).
2 5'-Carbamoyl derivatives of 2'-C-methyl-purine nucleosides as selective A1 adenosine receptor agonists: affinity, efficacy, and selectivity for A1 ... Bioorg Med Chem. 2008 Jan 1;16(1):336-53.
3 2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists. Bioorg Med Chem. 2010 Mar 15;18(6):2195-2203.
4 Adenosine receptor agonists: synthesis and biological evaluation of 1-deaza analogues of adenosine derivatives. J Med Chem. 1988 Jun;31(6):1179-83.
5 Semi-rational design of (north)-methanocarba nucleosides as dual acting A(1) and A(3) adenosine receptor agonists: novel prototypes for cardioprote... J Med Chem. 2005 Dec 29;48(26):8103-7.
6 Activity of N6-substituted 2-chloroadenosines at A1 and A2 adenosine receptors. J Med Chem. 1991 Dec;34(12):3388-90.
7 Inhibition of nucleoside transport proteins by C8-alkylamine-substituted purines. J Med Chem. 2005 Jan 13;48(1):321-9.