(1S,2R,3S,4R,5S)-4-(6-(3-chlorobenzylamino)-2-(pent-1-ynyl)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

ID: ALA258421

PubChem CID: 44449034

Max Phase: Preclinical

Molecular Formula: C25H27ClN6O3

Molecular Weight: 494.98

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CCCC#Cc1nc(NCc2cccc(Cl)c2)c2ncn([C@H]3[C@H](O)[C@H](O)[C@]4(C(=O)NC)C[C@H]34)c2n1

Standard InChI:  InChI=1S/C25H27ClN6O3/c1-3-4-5-9-17-30-22(28-12-14-7-6-8-15(26)10-14)18-23(31-17)32(13-29-18)19-16-11-25(16,24(35)27-2)21(34)20(19)33/h6-8,10,13,16,19-21,33-34H,3-4,11-12H2,1-2H3,(H,27,35)(H,28,30,31)/t16-,19-,20+,21+,25+/m1/s1

Standard InChI Key:  XISXDNOGOLBYIS-YZSDQEEOSA-N

Molfile:  

     RDKit          2D

 36 40  0  0  1  0  0  0  0  0999 V2000
   10.4333  -22.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2583  -22.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5151  -22.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4807  -22.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7527  -22.0562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5088  -23.2686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0526  -22.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2994  -21.7517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9475  -23.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7424  -23.4597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3736  -20.9656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5486  -20.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6295  -21.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9610  -22.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0464  -23.0522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7995  -23.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4682  -22.8997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3794  -22.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0457  -21.5963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1808  -22.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8427  -21.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0939  -21.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4691  -20.9882    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8002  -21.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4665  -21.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2191  -21.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8850  -21.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7972  -20.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0378  -20.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3751  -20.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6393  -21.6279    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.8865  -24.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9732  -25.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0603  -25.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3933  -26.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4803  -27.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
  3  8  1  1
 17 18  2  0
 18 13  1  0
  1  2  1  0
 18 19  1  0
 21 20  1  0
 22 21  1  0
 20 22  1  0
  1  9  1  6
 20  4  1  1
  2 10  1  6
  8 14  1  0
 21 23  1  1
 19 24  1  0
  4  5  1  0
 24 25  1  0
 13 11  1  0
 25 26  2  0
 11 12  2  0
 26 27  1  0
 12  8  1  0
 27 28  2  0
  2  3  1  0
 28 29  1  0
  4  6  2  0
 29 30  2  0
 30 25  1  0
 13 14  2  0
 27 31  1  0
  3 21  1  0
 16 32  1  0
 14 15  1  0
 32 33  3  0
  5  7  1  0
 33 34  1  0
 15 16  2  0
 34 35  1  0
 20  1  1  0
 35 36  1  0
M  END

Associated Targets(Human)

ADORA1 Tclin Adenosine receptors; A1 & A3 (1051 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA2A Tclin Adenosine A2a receptor (16305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA1 Tclin Adenosine A1 receptor (17603 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Adora1 Adenosine A1 receptor (162 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adora3 Adenosine A3 receptor (257 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adora2a Adenosine A2a receptor (87 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Biocomponents

Calculated Properties

Molecular Weight: 494.98Molecular Weight (Monoisotopic): 494.1833AlogP: 2.27#Rotatable Bonds: 6
Polar Surface Area: 125.19Molecular Species: NEUTRALHBA: 8HBD: 4
#RO5 Violations: HBA (Lipinski): 9HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 13.12CX Basic pKa: 3.92CX LogP: 2.94CX LogD: 2.94
Aromatic Rings: 3Heavy Atoms: 35QED Weighted: 0.39Np Likeness Score: -0.14

References

1. Melman A, Gao ZG, Kumar D, Wan TC, Gizewski E, Auchampach JA, Jacobson KA..  (2008)  Design of (N)-methanocarba adenosine 5'-uronamides as species-independent A3 receptor-selective agonists.,  18  (9): [PMID:18424135] [10.1016/j.bmcl.2008.04.001]

Source