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

ID: ALA402574

PubChem CID: 44449113

Max Phase: Preclinical

Molecular Formula: C22H21ClN6O3

Molecular Weight: 452.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#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/C22H21ClN6O3/c1-3-14-27-19(25-9-11-5-4-6-12(23)7-11)15-20(28-14)29(10-26-15)16-13-8-22(13,21(32)24-2)18(31)17(16)30/h1,4-7,10,13,16-18,30-31H,8-9H2,2H3,(H,24,32)(H,25,27,28)/t13-,16-,17+,18+,22+/m1/s1

Standard InChI Key:  LUOMIGGBSDWMMY-QKWCYAJMSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA402574

   (1S,2R,3S,4R,5S)-4-[6-[(3-chlorophenyl)methylamino]-2-ethynylpurin-9-yl]-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 452.90

Molecular Weight (Monoisotopic): 452.1364

AlogP: 1.10

#Rotatable Bonds: 5

Polar Surface Area: 125.19

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.13

CX Basic pKa: 3.99

CX LogP: 1.38

CX LogD: 1.38

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -0.35

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

Source(1):

• Scientific Literature