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

ID: ALA2402025

PubChem CID: 71764238

Max Phase: Preclinical

Molecular Formula: C29H28N6O6S

Molecular Weight: 588.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)[C@@]12C[C@@H]1[C@@H](n1cnc3c(NCCc4ccc(S(=O)(=O)O)cc4)nc(C#Cc4ccccc4)nc31)[C@H](O)[C@@H]2O

Standard InChI:  InChI=1S/C29H28N6O6S/c1-30-28(38)29-15-20(29)23(24(36)25(29)37)35-16-32-22-26(31-14-13-18-7-10-19(11-8-18)42(39,40)41)33-21(34-27(22)35)12-9-17-5-3-2-4-6-17/h2-8,10-11,16,20,23-25,36-37H,13-15H2,1H3,(H,30,38)(H,31,33,34)(H,39,40,41)/t20-,23-,24+,25+,29+/m1/s1

Standard InChI Key:  CWXDUDVELGRJRG-YUBGWGQWSA-N

Molfile:  

     RDKit          2D

 43 48  0  0  0  0  0  0  0  0999 V2000
   29.3859  -24.6024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7986  -25.3123    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.2070  -24.5999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5679  -29.4133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2776  -29.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2747  -28.1812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5661  -27.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8599  -29.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8611  -28.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0806  -27.9283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5969  -28.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0786  -29.2568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5643  -26.9588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9859  -29.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6896  -29.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3966  -30.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3912  -31.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0973  -31.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8067  -31.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8055  -30.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0988  -29.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8232  -30.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8214  -31.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3026  -30.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1197  -30.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0728  -32.1338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3827  -31.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6366  -31.2484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4669  -32.3947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9748  -31.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0445  -31.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0380  -30.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3320  -30.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2711  -26.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8194  -29.4890    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.9797  -26.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6865  -26.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3913  -26.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0976  -26.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0963  -25.7272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3827  -25.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6793  -25.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5117  -25.7222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
  7 13  1  0
  5 14  1  0
 14 15  3  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 32  1  0
 31 23  1  0
 23 24  1  0
 24 22  1  0
 22 12  1  1
 24 25  1  6
 23 26  1  6
 31 27  1  1
 27 28  1  0
 27 29  2  0
 28 30  1  0
 32 31  1  0
 32 33  1  0
 31 33  1  0
 13 34  1  0
 32 35  1  1
 34 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 37  1  0
 40  2  1  0
  2 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2402025

   4-[2-[[9-[(1S,2R,3S,4R,5S)-3,4-dihydroxy-5-(methylcarbamoyl)-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: 588.65

Molecular Weight (Monoisotopic): 588.1791

AlogP: 1.16

#Rotatable Bonds: 7

Polar Surface Area: 179.56

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -2.32

CX Basic pKa: 3.41

CX LogP: -1.38

CX LogD: -0.34

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.16

Np Likeness Score: -0.20

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