5-(3-((3-(2-ethylphenyl)-4,6-dioxo-2-thioxo-tetrahydropyrimidin-5(6H)-ylidene)methyl)-2,5-dimethyl-1H-pyrrol-1-yl)isophthalic acid

ID: ALA561044

Chembl Id: CHEMBL561044

PubChem CID: 5938528

Max Phase: Preclinical

Molecular Formula: C27H23N3O6S

Molecular Weight: 517.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccccc1N1C(=O)/C(=C\c2cc(C)n(-c3cc(C(=O)O)cc(C(=O)O)c3)c2C)C(=O)NC1=S

Standard InChI:  InChI=1S/C27H23N3O6S/c1-4-16-7-5-6-8-22(16)30-24(32)21(23(31)28-27(30)37)13-17-9-14(2)29(15(17)3)20-11-18(25(33)34)10-19(12-20)26(35)36/h5-13H,4H2,1-3H3,(H,33,34)(H,35,36)(H,28,31,37)/b21-13-

Standard InChI Key:  MMQRSFFSKMGAMF-BKUYFWCQSA-N

Alternative Forms

1. Parent:

   

   ALA561044

   5-[3-[(Z)-[1-(2-ethylphenyl)-4,6-dioxo-2-sulfanylidene-1,3-diazinan-5-ylidene]methyl]-2,5-dimethylpyrrol-1-yl]benzene-1,3-dicarboxylic 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: 517.56

Molecular Weight (Monoisotopic): 517.1308

AlogP: 3.88

#Rotatable Bonds: 6

Polar Surface Area: 128.94

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.44

CX Basic pKa: ┄

CX LogP: 5.19

CX LogD: -1.62

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.26

Np Likeness Score: -1.41

References

1. Perdih A, Kovac A, Wolber G, Blanot D, Gobec S, Solmajer T..  (2009)  Discovery of novel benzene 1,3-dicarboxylic acid inhibitors of bacterial MurD and MurE ligases by structure-based virtual screening approach.,  19  (10): [PMID:19369074] [10.1016/j.bmcl.2009.03.141]

2. Perdih A, Hrast M, Barreteau H, Gobec S, Wolber G, Solmajer T..  (2014)  Benzene-1,3-dicarboxylic acid 2,5-dimethylpyrrole derivatives as multiple inhibitors of bacterial Mur ligases (MurC-MurF).,  22  (15): [PMID:24953950] [10.1016/j.bmc.2014.05.058]

Source

Source(1):

• Scientific Literature