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

ID: ALA257573

PubChem CID: 44448952

Max Phase: Preclinical

Molecular Formula: C30H35ClN8O5

Molecular Weight: 623.11

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C30H35ClN8O5/c1-17(40)33-11-12-34-21(41)10-5-3-4-7-18-8-6-9-19(13-18)15-35-26-22-27(38-29(31)37-26)39(16-36-22)23-20-14-30(20,28(44)32-2)25(43)24(23)42/h6,8-9,13,16,20,23-25,42-43H,3,5,10-12,14-15H2,1-2H3,(H,32,44)(H,33,40)(H,34,41)(H,35,37,38)/t20-,23-,24+,25+,30+/m1/s1

Standard InChI Key:  WKBUSKLONVNTOQ-PXZSTNMRSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA257573

   (1S,2R,3S,4R,5S)-4-[6-[[3-[6-(2-acetamidoethylamino)-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: 623.11

Molecular Weight (Monoisotopic): 622.2419

AlogP: 0.89

#Rotatable Bonds: 11

Polar Surface Area: 183.39

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 13.12

CX Basic pKa: 2.14

CX LogP: 0.08

CX LogD: 0.08

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.10

Np Likeness Score: -0.26

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