2-(3-hydroxy-5-methyl-1-(2-(phenylsulfonyl)benzyl)-1H-pyrazol-4-yl)acetic acid

ID: ALA2385114

PubChem CID: 67607141

Max Phase: Preclinical

Molecular Formula: C19H18N2O5S

Molecular Weight: 386.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CC(=O)O)c(=O)[nH]n1Cc1ccccc1S(=O)(=O)c1ccccc1

Standard InChI:  InChI=1S/C19H18N2O5S/c1-13-16(11-18(22)23)19(24)20-21(13)12-14-7-5-6-10-17(14)27(25,26)15-8-3-2-4-9-15/h2-10H,11-12H2,1H3,(H,20,24)(H,22,23)

Standard InChI Key:  VYGBUYKFDBCDJZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   23.8813  -32.0373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8855  -31.2123    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.1690  -31.6211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6683  -29.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2486  -29.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6550  -30.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4809  -30.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8987  -29.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4899  -29.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3854  -32.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2105  -32.0748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4671  -31.2908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7980  -30.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1323  -31.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4111  -30.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3975  -30.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1048  -29.6445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6761  -29.6680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7964  -29.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2901  -31.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7105  -31.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1211  -31.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9454  -31.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3587  -31.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9418  -30.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1189  -30.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8998  -32.7412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 13 19  1  0
 12 20  1  0
 20  6  1  0
  7  2  1  0
  2 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 10 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385114

   2-[2-[[2-(benzenesulfonyl)phenyl]methyl]-3-methyl-5-oxo-1H-pyrazol-4-yl]acetic acid

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: 386.43

Molecular Weight (Monoisotopic): 386.0936

AlogP: 1.99

#Rotatable Bonds: 6

Polar Surface Area: 109.23

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.35

CX Basic pKa: ┄

CX LogP: 1.54

CX LogD: -1.89

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -0.99

References

1. Andrés M, Bravo M, Buil MA, Calbet M, Castro J, Domènech T, Eichhorn P, Ferrer M, Gómez E, Lehner MD, Moreno I, Roberts RS, Sevilla S..  (2013)  2-(1H-Pyrazol-4-yl)acetic acids as CRTh2 antagonists.,  23  (11): [PMID:23601708] [10.1016/j.bmcl.2013.03.093]

Source

Source(1):

• Scientific Literature