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

ID: ALA561165

Chembl Id: CHEMBL561165

PubChem CID: 1805059

Max Phase: Preclinical

Molecular Formula: C25H18ClN3O6S

Molecular Weight: 523.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(/C=C2/C(=O)NC(=S)N(c3cccc(Cl)c3)C2=O)c(C)n1-c1cc(C(=O)O)cc(C(=O)O)c1

Standard InChI:  InChI=1S/C25H18ClN3O6S/c1-12-6-14(13(2)28(12)19-8-15(23(32)33)7-16(9-19)24(34)35)10-20-21(30)27-25(36)29(22(20)31)18-5-3-4-17(26)11-18/h3-11H,1-2H3,(H,32,33)(H,34,35)(H,27,30,36)/b20-10-

Standard InChI Key:  JICUQZNLMIVTEY-JMIUGGIZSA-N

Alternative Forms

1. Parent:

   

   ALA561165

   5-(3-{(Z)-[1-(3-chlorophenyl)-4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene]methyl}-2,5-dimethyl-1H-pyrrol-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: 523.95

Molecular Weight (Monoisotopic): 523.0605

AlogP: 3.98

#Rotatable Bonds: 5

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: 4.83

CX LogD: -1.98

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.26

Np Likeness Score: -1.66

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