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

ID: ALA1084521

PubChem CID: 46866791

Max Phase: Preclinical

Molecular Formula: C23H15ClN2O6

Molecular Weight: 450.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cc(Cl)ccc1C(=O)O)c1ccc2c(c1)C(=O)N(c1ccc(CO)cc1)C2=O

Standard InChI:  InChI=1S/C23H15ClN2O6/c24-14-4-8-17(23(31)32)19(10-14)25-20(28)13-3-7-16-18(9-13)22(30)26(21(16)29)15-5-1-12(11-27)2-6-15/h1-10,27H,11H2,(H,25,28)(H,31,32)

Standard InChI Key:  SCXJOBPTOYBNRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   14.5099  -23.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2247  -23.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9412  -23.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9383  -22.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.6512  -21.9478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3672  -22.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0802  -21.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3704  -23.1826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7946  -22.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.2862  -20.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.5391  -20.0739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5944  -21.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0081  -22.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8323  -22.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2438  -21.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8251  -20.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0022  -20.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2245  -24.4319    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.2212  -21.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9345  -20.7149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5055  -20.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0688  -21.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4841  -22.2289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
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 14 15  2  0
 28 29  1  0
 28 30  2  0
  6 28  1  0
  1  2  2  0
 24 31  1  0
  5  7  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1084521

   4-Chloro-2-{[2-(4-hydroxymethylphenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-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: 450.83

Molecular Weight (Monoisotopic): 450.0619

AlogP: 3.58

#Rotatable Bonds: 5

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: 3.81

CX LogD: 0.45

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.51

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