5-Chloro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid

ID: ALA3717162

PubChem CID: 25161302

Max Phase: Preclinical

Molecular Formula: C22H22ClNO3

Molecular Weight: 383.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=Cc1c(C)cccc1C(=O)NC1(C(=O)O)Cc2ccc(Cl)cc2C1

Standard InChI:  InChI=1S/C22H22ClNO3/c1-13(2)9-19-14(3)5-4-6-18(19)20(25)24-22(21(26)27)11-15-7-8-17(23)10-16(15)12-22/h4-10H,11-12H2,1-3H3,(H,24,25)(H,26,27)

Standard InChI Key:  KVHVXSLWWFDHJQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    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
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8638   -6.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6020   -5.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8404   -3.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3404   -3.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5809   -2.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214   -1.2765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3809   -2.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3030    1.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6951    2.3582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5030    1.3331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638   -6.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022   -5.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7732   -7.5190    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
   -1.0028    1.5132    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
   -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
    1.1014   -5.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3647   -6.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8353   -6.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9758   -7.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3560    1.3452    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 18  1  0
 17  3  1  0
  1  3  1  0
 14  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7 15  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9  1  1  0
  1 11  1  0
 11 12  1  0
 11 13  2  0
 14 15  1  0
 14 16  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 15 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 20 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3717162

   5-Chloro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic 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: 383.88

Molecular Weight (Monoisotopic): 383.1288

AlogP: 4.42

#Rotatable Bonds: 4

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.85

CX Basic pKa: ┄

CX LogP: 5.35

CX LogD: 2.11

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -0.36

References

1.  (2010)  Substituted benzoylamino-indan-2-carboxylic acids and related compounds, 

Source

Source(1):

• Patent Bioactivity Data