4-(2-(9-((1S,2R,3S,4R,5R)-3,4-Dihydroxybicyclo[3.1.0]hexan-2-yl)-2-(phenylethynyl)-9H-purin-6-ylamino)ethyl)-benzenesulfonic acid

ID: ALA2402023

PubChem CID: 71764236

Max Phase: Preclinical

Molecular Formula: C27H25N5O5S

Molecular Weight: 531.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(O)c1ccc(CCNc2nc(C#Cc3ccccc3)nc3c2ncn3[C@H]2[C@H](O)[C@H](O)[C@@H]3C[C@@H]32)cc1

Standard InChI:  InChI=1S/C27H25N5O5S/c33-24-20-14-19(20)23(25(24)34)32-15-29-22-26(28-13-12-17-6-9-18(10-7-17)38(35,36)37)30-21(31-27(22)32)11-8-16-4-2-1-3-5-16/h1-7,9-10,15,19-20,23-25,33-34H,12-14H2,(H,28,30,31)(H,35,36,37)/t19-,20+,23+,24+,25-/m0/s1

Standard InChI Key:  ODDDHQVHKBFNES-IRYUZJHDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2402023

   4-[2-[[9-[(1S,2R,3S,4R,5R)-3,4-dihydroxy-2-bicyclo[3.1.0]hexanyl]-2-(2-phenylethynyl)purin-6-yl]amino]ethyl]benzenesulfonic 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: 531.59

Molecular Weight (Monoisotopic): 531.1576

AlogP: 2.04

#Rotatable Bonds: 6

Polar Surface Area: 150.46

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -2.06

CX Basic pKa: 2.98

CX LogP: -0.35

CX LogD: 0.60

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.22

Np Likeness Score: -0.25

References

1. Paoletta S, Tosh DK, Finley A, Gizewski ET, Moss SM, Gao ZG, Auchampach JA, Salvemini D, Jacobson KA..  (2013)  Rational design of sulfonated A3 adenosine receptor-selective nucleosides as pharmacological tools to study chronic neuropathic pain.,  56  (14): [PMID:23789857] [10.1021/jm4007966]

Source

Source(1):

• Scientific Literature