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-ynoic acid

ID: ALA257833

PubChem CID: 44232535

Max Phase: Preclinical

Molecular Formula: C26H27ClN6O5

Molecular Weight: 538.99

Molecule Type: Small molecule

Names and Identifiers

Synonyms: MRS-5151 | CHEMBL257833|MRS-5151|BDBM50377686

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

Standard InChI:  InChI=1S/C26H27ClN6O5/c1-28-25(38)26-11-16(26)20(21(36)22(26)37)33-13-30-19-23(29-12-14-6-5-7-15(27)10-14)31-17(32-24(19)33)8-3-2-4-9-18(34)35/h5-7,10,13,16,20-22,36-37H,2,4,9,11-12H2,1H3,(H,28,38)(H,34,35)(H,29,31,32)/t16-,20-,21+,22+,26+/m1/s1

Standard InChI Key:  VWHZKAYCOHCKRI-CSTWGOEFSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA257833

   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-ynoic acid

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: 538.99

Molecular Weight (Monoisotopic): 538.1731

AlogP: 1.73

#Rotatable Bonds: 8

Polar Surface Area: 162.49

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.41

CX Basic pKa: 4.04

CX LogP: 1.14

CX LogD: -1.36

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.21

Np Likeness Score: -0.03

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]

2. Tosh DK, Chinn M, Ivanov AA, Klutz AM, Gao ZG, Jacobson KA..  (2009)  Functionalized congeners of A3 adenosine receptor-selective nucleosides containing a bicyclo[3.1.0]hexane ring system.,  52  (23): [PMID:19499950] [10.1021/jm900426g]

Source

Source(1):

• Scientific Literature