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

ID: ALA1084248

PubChem CID: 46868657

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(c1ccc(O)cc1)C2=O

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

Standard InChI Key:  SEVZMDZOXGHKNY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    4.0027   -7.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0016   -8.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7164   -8.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4328   -8.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4300   -7.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7146   -7.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1429   -7.3103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8589   -7.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5718   -7.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8620   -8.5451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2862   -7.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2750   -6.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5655   -6.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9960   -6.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9981   -7.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7812   -7.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2632   -6.8860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7778   -6.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0380   -8.3368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0308   -5.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0861   -6.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4998   -7.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3240   -7.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7355   -6.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3168   -6.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4939   -6.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7162   -9.7944    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.7129   -6.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4261   -6.0774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9972   -6.0817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5605   -6.8785    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
 24 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1084248

   4-Chloro-2-[[2-(4-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: 0.90

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -1.15

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