(Z)-3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-N-(3-(methylthio)propyl)-2-oxoindoline-6-carboxamide

ID: ALA3621300

PubChem CID: 56932528

Max Phase: Preclinical

Molecular Formula: C20H23N3O2S

Molecular Weight: 369.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSCCCNC(=O)c1ccc2c(c1)NC(=O)/C2=C\c1[nH]c(C)cc1C

Standard InChI:  InChI=1S/C20H23N3O2S/c1-12-9-13(2)22-17(12)11-16-15-6-5-14(10-18(15)23-20(16)25)19(24)21-7-4-8-26-3/h5-6,9-11,22H,4,7-8H2,1-3H3,(H,21,24)(H,23,25)/b16-11-

Standard InChI Key:  VCJNXPLAUFQNOZ-WJDWOHSUSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7388    1.9224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0412    2.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7359    4.1352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449    4.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7889    0.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433    5.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1353    2.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187   -1.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267   -2.9927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6549   -0.8867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9300   -3.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9380   -5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2413   -5.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2494   -7.4828    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2914   -8.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  2  0
  8 16  2  0
 15 17  1  0
 13 18  1  0
  2 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3621300

   (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-N-(3-methylsulfanylpropyl)-2-oxo-1H-indole-6-carboxamide

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: 369.49

Molecular Weight (Monoisotopic): 369.1511

AlogP: 3.61

#Rotatable Bonds: 6

Polar Surface Area: 73.99

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.08

CX Basic pKa: ┄

CX LogP: 3.06

CX LogD: 3.06

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: -0.87

References

1. Patel H, Chuckowree I, Coxhead P, Guille M, Wang M, Zuckermann A, Williams RSB, Librizzi M, Paranal RM, Bradner JE, Spencer J.  (2014)  Synthesis of hybrid anticancer agents based on kinase and histone deacetylase inhibitors,  5  (12): [10.1039/C4MD00211C]

Source

Source(1):

• Scientific Literature