2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-5-(3-(4-sulfamoylphenethyl)thioureido)benzoic acid

ID: ALA1232755

Chembl Id: CHEMBL1232755

Max Phase: Preclinical

Molecular Formula: C29H23N3O7S2

Molecular Weight: 589.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(CCNC(=S)Nc2ccc(-c3c4ccc(=O)cc-4oc4cc(O)ccc34)c(C(=O)O)c2)cc1

Standard InChI:  InChI=1S/C29H23N3O7S2/c30-41(37,38)20-6-1-16(2-7-20)11-12-31-29(40)32-17-3-8-21(24(13-17)28(35)36)27-22-9-4-18(33)14-25(22)39-26-15-19(34)5-10-23(26)27/h1-10,13-15,33H,11-12H2,(H,35,36)(H2,30,37,38)(H2,31,32,40)

Standard InChI Key:  ZXJGFVGTIKDQMI-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1232755

   ---

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: 589.65

Molecular Weight (Monoisotopic): 589.0977

AlogP: 4.15

#Rotatable Bonds: 7

Polar Surface Area: 171.96

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.57

CX Basic pKa: 2.82

CX LogP: 3.25

CX LogD: -0.71

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.14

Np Likeness Score: -0.55

References

1. Sethi KK, Vullo D, Verma SM, Tanç M, Carta F, Supuran CT..  (2013)  Carbonic anhydrase inhibitors: synthesis and inhibition of the human carbonic anhydrase isoforms I, II, VII, IX and XII with benzene sulfonamides incorporating 4,5,6,7-tetrabromophthalimide moiety.,  21  (19): [PMID:23965175] [10.1016/j.bmc.2013.07.044]

2. De Luca L, Ferro S, Damiano FM, Supuran CT, Vullo D, Chimirri A, Gitto R..  (2014)  Structure-based screening for the discovery of new carbonic anhydrase VII inhibitors.,  71  [PMID:24287559] [10.1016/j.ejmech.2013.10.071]

3. Żołnowska B, Sławiński J, Pogorzelska A, Chojnacki J, Vullo D, Supuran CT..  (2014)  Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII.,  71  [PMID:24291567] [10.1016/j.ejmech.2013.10.081]

4. Sethi KK, Verma SM, Tanç M, Purper G, Calafato G, Carta F, Supuran CT..  (2014)  Carbonic anhydrase inhibitors: synthesis and inhibition of the human carbonic anhydrase isoforms I, II, IX and XII with benzene sulfonamides incorporating 4- and 3-nitrophthalimide moieties.,  22  (5): [PMID:24513184] [10.1016/j.bmc.2014.01.031]

5. Carta F, Ferraroni M, Scozzafava A, Supuran CT..  (2016)  Fluorescent sulfonamide carbonic anhydrase inhibitors incorporating 1,2,3-triazole moieties: Kinetic and X-ray crystallographic studies.,  24  (2): [PMID:26682703] [10.1016/j.bmc.2015.11.031]

Source

Source(1):

• Scientific Literature