2-[4-(2-Chloro-5-hydroxy-4-methoxy-phenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-ylsulfanyl]-N,N-dimethylacetamide

ID: ALA2158561

PubChem CID: 25216601

Max Phase: Preclinical

Molecular Formula: C18H16ClN5O3S

Molecular Weight: 417.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Cl)c(-c2nc(SCC(=O)N(C)C)nc3[nH]cc(C#N)c23)cc1O

Standard InChI:  InChI=1S/C18H16ClN5O3S/c1-24(2)14(26)8-28-18-22-16(15-9(6-20)7-21-17(15)23-18)10-4-12(25)13(27-3)5-11(10)19/h4-5,7,25H,8H2,1-3H3,(H,21,22,23)

Standard InChI Key:  CNCOWHMBYWEBGS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.7828  -19.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7816  -20.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4972  -20.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2143  -20.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2113  -19.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4953  -18.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4988  -21.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7819  -21.6541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7814  -22.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4970  -22.8930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2116  -21.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2145  -22.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9988  -22.7279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4808  -22.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9942  -21.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0662  -20.4174    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.2448  -20.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4973  -19.8240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0659  -22.8915    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.3510  -22.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9250  -18.7577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6356  -22.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4929  -17.9379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2067  -17.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9207  -22.4770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6350  -23.7162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2052  -22.8894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9213  -21.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
  7  8  2  0
  2 16  1  0
  8  9  1  0
 17 18  3  0
 15 17  1  0
  4  5  1  0
  9 19  1  0
  9 10  2  0
 19 20  1  0
 10 12  1  0
  5 21  1  0
 11  7  1  0
 20 22  1  0
  3  7  1  0
  6 23  1  0
 11 12  2  0
 23 24  1  0
  2  3  1  0
 22 25  1  0
  5  6  2  0
 22 26  2  0
  6  1  1  0
 25 27  1  0
  1  2  2  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2158561

   2-[[4-(2-chloro-5-hydroxy-4-methoxyphenyl)-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-2-yl]sulfanyl]-N,N-dimethylacetamide

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: 417.88

Molecular Weight (Monoisotopic): 417.0662

AlogP: 3.04

#Rotatable Bonds: 5

Polar Surface Area: 115.13

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.25

CX Basic pKa: 3.23

CX LogP: 2.66

CX LogD: 2.61

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.48

Np Likeness Score: -1.10

References

1. Davies NG, Browne H, Davis B, Drysdale MJ, Foloppe N, Geoffrey S, Gibbons B, Hart T, Hubbard R, Jensen MR, Mansell H, Massey A, Matassova N, Moore JD, Murray J, Pratt R, Ray S, Robertson A, Roughley SD, Schoepfer J, Scriven K, Simmonite H, Stokes S, Surgenor A, Webb P, Wood M, Wright L, Brough P..  (2012)  Targeting conserved water molecules: design of 4-aryl-5-cyanopyrrolo[2,3-d]pyrimidine Hsp90 inhibitors using fragment-based screening and structure-based optimization.,  20  (22): [PMID:23018093] [10.1016/j.bmc.2012.08.050]

Source

Source(1):

• Scientific Literature