2-Amino-5-(3,5-dichloro-phenylsulfanyl)-6-methyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one

ID: ALA196235

PubChem CID: 135964420

Max Phase: Preclinical

Molecular Formula: C13H10Cl2N4OS

Molecular Weight: 341.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2nc(N)nc(O)c2c1Sc1cc(Cl)cc(Cl)c1

Standard InChI:  InChI=1S/C13H10Cl2N4OS/c1-5-10(21-8-3-6(14)2-7(15)4-8)9-11(17-5)18-13(16)19-12(9)20/h2-4H,1H3,(H4,16,17,18,19,20)

Standard InChI Key:  UCKWWQJKSKXTDX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    2.4750   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -3.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -2.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625   -3.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -3.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -2.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -1.1917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -1.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9125   -0.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542   -3.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917    0.7583    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -2.0292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5750   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5  1  2  0
  6  5  1  0
  7  6  2  0
  8  2  1  0
  9  4  2  0
 10  4  1  0
 11 10  1  0
 12  5  1  0
 13 11  1  0
 14 11  2  0
 15 14  1  0
 16 13  2  0
 17 15  2  0
 18  7  1  0
 19 15  1  0
 20 16  1  0
 21  9  1  0
  8  9  1  0
  7  3  1  0
 16 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA196235

   ---

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: 341.22

Molecular Weight (Monoisotopic): 339.9952

AlogP: 4.01

#Rotatable Bonds: 2

Polar Surface Area: 87.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.81

CX Basic pKa: 2.26

CX LogP: 4.25

CX LogD: 4.25

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.66

Np Likeness Score: -0.94

References

1. Gangjee A, Jain HD, Kisliuk RL..  (2005)  Novel 2-amino-4-oxo-5-arylthio-substituted-pyrrolo[2,3-d]pyrimidines as nonclassical antifolate inhibitors of thymidylate synthase.,  15  (9): [PMID:15837298] [10.1016/j.bmcl.2005.03.029]

Source

Source(1):

• Scientific Literature