({2-methoxy-4-[2-({5-hydroxy-2-[(4-methoxybenzylamino)carbonyl]-4-oxo-4H-chromen-7-yl}oxy)ethyl]phenyl}amino)(oxo)acetic acid

ID: ALA242020

Chembl Id: CHEMBL242020

PubChem CID: 16756067

Max Phase: Preclinical

Molecular Formula: C29H26N2O10

Molecular Weight: 562.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CNC(=O)c2cc(=O)c3c(O)cc(OCCc4ccc(NC(=O)C(=O)O)c(OC)c4)cc3o2)cc1

Standard InChI:  InChI=1S/C29H26N2O10/c1-38-18-6-3-17(4-7-18)15-30-27(34)25-14-22(33)26-21(32)12-19(13-24(26)41-25)40-10-9-16-5-8-20(23(11-16)39-2)31-28(35)29(36)37/h3-8,11-14,32H,9-10,15H2,1-2H3,(H,30,34)(H,31,35)(H,36,37)

Standard InChI Key:  MLDHFNNJFGENAK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA242020

   [(4-{2-[(5-hydroxy-2-{[(4-methoxyphenyl)methyl]carbamoyl}-4-oxo-4H-chromen-7-yl)oxy]ethyl}-2-methoxyphenyl)carbamoyl]formic 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: 562.53

Molecular Weight (Monoisotopic): 562.1587

AlogP: 3.09

#Rotatable Bonds: 10

Polar Surface Area: 173.63

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.54

CX Basic pKa: ┄

CX LogP: 3.52

CX LogD: -0.31

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.21

Np Likeness Score: -0.41

References

1. Choi SR, Pradhan A, Hammond NL, Chittiboyina AG, Tekwani BL, Avery MA..  (2007)  Design, synthesis, and biological evaluation of Plasmodium falciparum lactate dehydrogenase inhibitors.,  50  (16): [PMID:17636950] [10.1021/jm070336k]

2. Dragovich PS, Fauber BP, Corson LB, Ding CZ, Eigenbrot C, Ge H, Giannetti AM, Hunsaker T, Labadie S, Liu Y, Malek S, Pan B, Peterson D, Pitts K, Purkey HE, Sideris S, Ultsch M, VanderPorten E, Wei B, Xu Q, Yen I, Yue Q, Zhang H, Zhang X..  (2013)  Identification of substituted 2-thio-6-oxo-1,6-dihydropyrimidines as inhibitors of human lactate dehydrogenase.,  23  (11): [PMID:23628333] [10.1016/j.bmcl.2013.04.001]

Source

Source(1):

• Scientific Literature