(3Z)-N-[(1S)-2-Hydroxy-1-phenylethyl]-3-(1H-imidazol-2-ylmethylidene)-2-oxoindole-5-carboxamide

ID: ALA4096476

PubChem CID: 137654589

Max Phase: Preclinical

Molecular Formula: C21H18N4O3

Molecular Weight: 374.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Nc2ccc(C(=O)N[C@H](CO)c3ccccc3)cc2/C1=C/c1ncc[nH]1

Standard InChI:  InChI=1S/C21H18N4O3/c26-12-18(13-4-2-1-3-5-13)25-20(27)14-6-7-17-15(10-14)16(21(28)24-17)11-19-22-8-9-23-19/h1-11,18,26H,12H2,(H,22,23)(H,24,28)(H,25,27)/b16-11-/t18-/m1/s1

Standard InChI Key:  VRXITTRKTGPRLP-MUMAZLPKSA-N

Molfile:  

     RDKit          2D

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    6.9015   -2.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1929   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4867   -3.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4879   -2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7117   -2.3001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2307   -2.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6140   -4.5943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3198   -3.3674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3223   -5.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7279   -3.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0243   -3.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6565   -4.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0516   -4.0236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3433   -4.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121   -5.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3246   -5.3173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 27 28  1  0
 28 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096476

   ---

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: 374.40

Molecular Weight (Monoisotopic): 374.1379

AlogP: 2.37

#Rotatable Bonds: 5

Polar Surface Area: 107.11

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.88

CX Basic pKa: 6.33

CX LogP: 1.54

CX LogD: 1.51

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.51

Np Likeness Score: -0.78

References

1. Guo J, Zhu M, Wu T, Hao C, Wang K, Yan Z, Huang W, Wang J, Zhao D, Cheng M..  (2017)  Discovery of indolin-2-one derivatives as potent PAK4 inhibitors: Structure-activity relationship analysis, biological evaluation and molecular docking study.,  25  (13): [PMID:28502459] [10.1016/j.bmc.2017.04.047]

Source

Source(1):

• Scientific Literature