{3-[5-(2-Hydroxyphenyl)-3-phenylpyrazol-1-yl]-2-oxo-2,3-dihydroindol-1-yl}acetic Acid

ID: ALA2172759

PubChem CID: 136237413

Max Phase: Preclinical

Molecular Formula: C25H19N3O4

Molecular Weight: 425.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CN1C(=O)C(n2nc(-c3ccccc3)cc2-c2ccccc2O)c2ccccc21

Standard InChI:  InChI=1S/C25H19N3O4/c29-22-13-7-5-10-17(22)21-14-19(16-8-2-1-3-9-16)26-28(21)24-18-11-4-6-12-20(18)27(25(24)32)15-23(30)31/h1-14,24,29H,15H2,(H,30,31)

Standard InChI Key:  PASUAPSWILNSJS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    4.0779   -6.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6732   -5.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2749   -7.0252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2856   -5.9941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524   -5.9241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1298   -5.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7870   -5.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159   -6.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9135   -7.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4862   -8.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6614   -8.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638   -7.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6910   -6.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1469   -4.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5767   -5.7131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2340   -6.2118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9113   -5.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6727   -4.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8479   -4.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6905   -6.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8453   -6.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6244   -7.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2488   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0941   -5.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3149   -5.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3769   -4.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7280   -3.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2570   -2.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4349   -2.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0838   -3.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5548   -4.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5501   -3.4408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  5 13  1  0
  8 13  2  0
  6 14  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 15 19  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 17 20  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 26 31  2  0
 27 32  1  0
 19 26  1  0
  7 15  1  0
  2  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2172759

   ---

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: 425.44

Molecular Weight (Monoisotopic): 425.1376

AlogP: 3.94

#Rotatable Bonds: 5

Polar Surface Area: 95.66

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.70

CX Basic pKa: 2.05

CX LogP: 3.79

CX LogD: 0.60

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -0.68

References

1. Havrylyuk D, Zimenkovsky B, Vasylenko O, Gzella A, Lesyk R..  (2012)  Synthesis of new 4-thiazolidinone-, pyrazoline-, and isatin-based conjugates with promising antitumor activity.,  55  (20): [PMID:22992049] [10.1021/jm300789g]

Source

Source(1):

• Scientific Literature