4-Chloro-2-{[2-(2-hydroxyphenyl)-1,3-dioxo-2,3-dihydro-1Hisoindole-5-carbonyl]amino}benzoic Acid

ID: ALA1083969

PubChem CID: 46868655

Max Phase: Preclinical

Molecular Formula: C22H13ClN2O6

Molecular Weight: 436.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cc(Cl)ccc1C(=O)O)c1ccc2c(c1)C(=O)N(c1ccccc1O)C2=O

Standard InChI:  InChI=1S/C22H13ClN2O6/c23-12-6-8-14(22(30)31)16(10-12)24-19(27)11-5-7-13-15(9-11)21(29)25(20(13)28)17-3-1-2-4-18(17)26/h1-10,26H,(H,24,27)(H,30,31)

Standard InChI Key:  YZCGUQOGRSEYPK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   14.3777   -3.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3766   -3.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0914   -4.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8078   -3.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8050   -3.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0896   -2.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5179   -2.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2339   -3.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9468   -2.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2370   -3.9493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6612   -3.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6500   -1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9405   -1.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3710   -1.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3731   -2.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1562   -2.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6382   -2.2901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1528   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4130   -3.7410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4058   -0.8406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4611   -2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8748   -3.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6990   -3.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1105   -2.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6918   -1.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8689   -1.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0912   -5.1985    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.0879   -1.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8011   -1.4816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3722   -1.4859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4634   -3.7187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0
  3  4  2  0
  7  8  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
  8  9  1  0
 16 19  2  0
  4  5  1  0
 18 20  2  0
  8 10  2  0
  2  3  1  0
 21 22  2  0
  9 11  2  0
 22 23  1  0
 11 15  1  0
 23 24  2  0
  5  6  2  0
 24 25  1  0
 14 12  1  0
 25 26  2  0
 26 21  1  0
 17 21  1  0
  6  1  1  0
  3 27  1  0
 12 13  2  0
 13  9  1  0
 14 15  2  0
 28 29  1  0
 28 30  2  0
  6 28  1  0
  1  2  2  0
 22 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1083969

   4-Chloro-2-[[2-(2-hydroxyphenyl)-1,3-dioxoisoindole-5-carbonyl]amino]benzoic 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: 436.81

Molecular Weight (Monoisotopic): 436.0462

AlogP: 3.80

#Rotatable Bonds: 4

Polar Surface Area: 124.01

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.55

CX Basic pKa: ┄

CX LogP: 4.28

CX LogD: 0.86

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -1.13

References

1. Odell LR, Howan D, Gordon CP, Robertson MJ, Chau N, Mariana A, Whiting AE, Abagyan R, Daniel JA, Gorgani NN, Robinson PJ, McCluskey A..  (2010)  The pthaladyns: GTP competitive inhibitors of dynamin I and II GTPase derived from virtual screening.,  53  (14): [PMID:20575553] [10.1021/jm100442u]

Source

Source(1):

• Scientific Literature