2-Sulfanilyl-6-(prop-2-ynyloxy)purine

ID: ALA4086832

PubChem CID: 137644104

Max Phase: Preclinical

Molecular Formula: C14H12N6O3S

Molecular Weight: 344.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCOc1nc(Nc2ccc(S(N)(=O)=O)cc2)nc2[nH]cnc12

Standard InChI:  InChI=1S/C14H12N6O3S/c1-2-7-23-13-11-12(17-8-16-11)19-14(20-13)18-9-3-5-10(6-4-9)24(15,21)22/h1,3-6,8H,7H2,(H2,15,21,22)(H2,16,17,18,19,20)

Standard InChI Key:  CACBKDPCTWIDGM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    8.4582  -18.7456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8749  -18.0330    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0495  -18.0285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4442  -18.4455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4431  -19.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1578  -19.6857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1560  -18.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8714  -18.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8762  -19.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6638  -19.5192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1456  -18.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6559  -18.1820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7282  -19.6848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0142  -19.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0193  -18.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3061  -18.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5903  -18.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5924  -19.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3062  -19.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1536  -17.2078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8752  -17.2088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4379  -16.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4354  -15.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4330  -15.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  5 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  7 20  1  0
 17  2  1  0
  2 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4086832

   ---

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: 344.36

Molecular Weight (Monoisotopic): 344.0692

AlogP: 0.76

#Rotatable Bonds: 5

Polar Surface Area: 135.88

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.93

CX Basic pKa: 2.21

CX LogP: 1.09

CX LogD: 1.08

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: -1.52

References

1. Coxon CR, Anscombe E, Harnor SJ, Martin MP, Carbain B, Golding BT, Hardcastle IR, Harlow LK, Korolchuk S, Matheson CJ, Newell DR, Noble ME, Sivaprakasam M, Tudhope SJ, Turner DM, Wang LZ, Wedge SR, Wong C, Griffin RJ, Endicott JA, Cano C..  (2017)  Cyclin-Dependent Kinase (CDK) Inhibitors: Structure-Activity Relationships and Insights into the CDK-2 Selectivity of 6-Substituted 2-Arylaminopurines.,  60  (5): [PMID:28005359] [10.1021/acs.jmedchem.6b01254]

Source

Source(1):

• Scientific Literature