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

ID: ALA257785

PubChem CID: 44448982

Max Phase: Preclinical

Molecular Formula: C28H33ClN8O4

Molecular Weight: 581.08

Molecule Type: Small molecule

Names and Identifiers

Synonyms: MRS-5166 | CHEMBL257785|MRS-5166|BDBM50377676

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

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

Standard InChI Key:  YREVRKNBIMSBSA-JIGPFOKVSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA257785

   (1S,2R,3S,4R,5S)-4-[2-[6-(2-aminoethylamino)-6-oxohex-1-ynyl]-6-[(3-chlorophenyl)methylamino]purin-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: 0.73

CX LogD: -1.03

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.15

Np Likeness Score: -0.22

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