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

ID: ALA256312

Cas Number: 1190215-78-1

PubChem CID: 44448951

Max Phase: Preclinical

Molecular Formula: C28H33ClN8O4

Molecular Weight: 581.08

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)[C@@]12C[C@@H]1[C@@H](n1cnc3c(NCc4cccc(C#CCCCC(=O)NCCN)c4)nc(Cl)nc31)[C@H](O)[C@@H]2O

Standard InChI:  InChI=1S/C28H33ClN8O4/c1-31-26(41)28-13-18(28)21(22(39)23(28)40)37-15-34-20-24(35-27(29)36-25(20)37)33-14-17-8-5-7-16(12-17)6-3-2-4-9-19(38)32-11-10-30/h5,7-8,12,15,18,21-23,39-40H,2,4,9-11,13-14,30H2,1H3,(H,31,41)(H,32,38)(H,33,35,36)/t18-,21-,22+,23+,28+/m1/s1

Standard InChI Key:  KLKGDSNZDPZCMZ-SGDVHKFBSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA256312

   (1S,2R,3S,4R,5S)-4-[6-[[3-[6-(2-aminoethylamino)-6-oxohex-1-ynyl]phenyl]methylamino]-2-chloropurin-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: 581.08

Molecular Weight (Monoisotopic): 580.2313

AlogP: 0.72

#Rotatable Bonds: 10

Polar Surface Area: 180.31

Molecular Species: BASE

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 13.12

CX Basic pKa: 9.16

CX LogP: 0.26

CX LogD: -1.49

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.11

Np Likeness Score: -0.20

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