2-(4-chlorophenyl)-10-thia-5,7,12-triazatetracyclo[11.7.0.0^{3,11}.0^{4,9}]icosa-1(13),2,4(9),5,7,11-hexaen-8-amine

ID: ALA1094018

PubChem CID: 46884407

Max Phase: Preclinical

Molecular Formula: C22H21ClN4S

Molecular Weight: 408.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1sc1nc3c(c(-c4ccc(Cl)cc4)c12)CCCCCCC3

Standard InChI:  InChI=1S/C22H21ClN4S/c23-14-10-8-13(9-11-14)17-15-6-4-2-1-3-5-7-16(15)27-22-18(17)19-20(28-22)21(24)26-12-25-19/h8-12H,1-7H2,(H2,24,25,26)

Standard InChI Key:  JGWFGPLJAWDQNW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   -1.1907   -9.1924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885   -7.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4742   -7.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4768   -8.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3144   -9.0428    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1908   -6.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743   -6.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4744   -5.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1903   -5.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076   -5.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9040   -6.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1919   -4.2391    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3185   -7.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8022   -8.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -8.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9700   -7.5328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4813   -6.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578   -6.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087   -8.9608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4322   -9.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2479   -9.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9548   -9.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9045   -8.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049   -7.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4298   -7.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401   -7.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2326   -8.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9476   -7.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 12  1  0
  5 14  1  0
 13  3  1  0
 13 14  2  0
  3  2  2  0
 14 15  1  0
  2 24  1  0
 15 16  2  0
  6  7  2  0
 16 17  1  0
  3  4  1  0
 17 18  2  0
 18 13  1  0
  7  8  1  0
 15 19  1  0
 23  1  1  0
  8  9  2  0
  1  4  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  2  6  1  0
  4  5  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 27 22  1  0
 27 28  1  0
 28 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094018

   2-(4-Chlorophenyl)-10-thia-5,7,12-triazatetracyclo[11.7.0.03,11.04,9]icosa-1(13),2,4(9),5,7,11-hexaen-8-amine

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: 408.96

Molecular Weight (Monoisotopic): 408.1175

AlogP: 6.19

#Rotatable Bonds: 1

Polar Surface Area: 64.69

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.65

CX LogP: 6.23

CX LogD: 6.23

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -1.16

References

1. Lockman JW, Reeder MD, Suzuki K, Ostanin K, Hoff R, Bhoite L, Austin H, Baichwal V, Adam Willardsen J..  (2010)  Inhibition of eEF2-K by thieno[2,3-b]pyridine analogues.,  20  (7): [PMID:20189382] [10.1016/j.bmcl.2010.02.005]

Source

Source(1):

• Scientific Literature