methyl 6-(6-(3-chlorobenzylamino)-9-((1S,2R,3S,4R,5S)-3,4-dihydroxy-5-(methylcarbamoyl)bicyclo[3.1.0]hexan-2-yl)-9H-purin-2-yl)hex-5-ynoate

ID: ALA436649

PubChem CID: 44449007

Max Phase: Preclinical

Molecular Formula: C27H29ClN6O5

Molecular Weight: 553.02

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H29ClN6O5/c1-29-26(38)27-12-17(27)21(22(36)23(27)37)34-14-31-20-24(30-13-15-7-6-8-16(28)11-15)32-18(33-25(20)34)9-4-3-5-10-19(35)39-2/h6-8,11,14,17,21-23,36-37H,3,5,10,12-13H2,1-2H3,(H,29,38)(H,30,32,33)/t17-,21-,22+,23+,27+/m1/s1

Standard InChI Key:  SIECIRCONJTJAI-SASJIJFGSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA436649

   methyl 6-[6-[(3-chlorophenyl)methylamino]-9-[(1S,2R,3S,4R,5S)-3,4-dihydroxy-5-(methylcarbamoyl)-2-bicyclo[3.1.0]hexanyl]purin-2-yl]hex-5-ynoate

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: 553.02

Molecular Weight (Monoisotopic): 552.1888

AlogP: 1.82

#Rotatable Bonds: 8

Polar Surface Area: 151.49

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.12

CX Basic pKa: 3.92

CX LogP: 2.17

CX LogD: 2.17

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.19

Np Likeness Score: -0.06

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