3,3-dimethyl-6-(2-methylpyrimidin-5-yl)-1-(1H-pyrrolo[2,3-c]pyridin-4-yl)indolin-2-one

ID: ALA4212469

PubChem CID: 129104202

Max Phase: Preclinical

Molecular Formula: C22H19N5O

Molecular Weight: 369.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ncc(-c2ccc3c(c2)N(c2cncc4[nH]ccc24)C(=O)C3(C)C)cn1

Standard InChI:  InChI=1S/C22H19N5O/c1-13-25-9-15(10-26-13)14-4-5-17-19(8-14)27(21(28)22(17,2)3)20-12-23-11-18-16(20)6-7-24-18/h4-12,24H,1-3H3

Standard InChI Key:  GXJMSBHSODGFPG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.4137   -2.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1194   -1.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2207   -2.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2196   -3.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9276   -3.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9258   -1.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5135   -3.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8058   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0982   -3.6305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972   -4.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8095   -4.8575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5141   -4.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6345   -2.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6393   -3.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4237   -3.4755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9037   -2.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7209   -2.8015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4086   -4.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6918   -4.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6765   -5.5040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3771   -5.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897   -4.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1065   -4.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0904   -5.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8562   -5.7878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3457   -5.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8822   -4.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
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  6 15  2  0
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  7  4  1  0
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  5  8  1  0
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  2 14  1  0
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 16 19  1  0
 11 23  1  0
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 25 26  1  0
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 27 28  2  0
 28 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4212469

   ---

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: 369.43

Molecular Weight (Monoisotopic): 369.1590

AlogP: 4.28

#Rotatable Bonds: 2

Polar Surface Area: 74.77

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.66

CX Basic pKa: 4.77

CX LogP: 2.88

CX LogD: 2.88

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: -0.32

References

1. Rosse G..  (2017)  Indolinone Inhibitors of ENT1 for the Treatment of Schizophrenia.,  8  (10): [PMID:29057039] [10.1021/acsmedchemlett.7b00378]

Source

Source(1):

• Scientific Literature