ID: ALA332993

Max Phase: Preclinical

Molecular Formula: C27H24N2O5

Molecular Weight: 456.50

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccn2c1Cc1ccccc1-c1ccccc1

Standard InChI:  InChI=1S/C27H24N2O5/c1-2-19-21(15-18-11-6-7-12-20(18)17-9-4-3-5-10-17)29-14-8-13-22(34-16-23(30)31)25(29)24(19)26(32)27(28)33/h3-14H,2,15-16H2,1H3,(H2,28,33)(H,30,31)

Standard InChI Key:  UWYANTZRSJRLJO-UHFFFAOYSA-N

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

Properties

Molecular Weight: 456.50

Molecular Weight (Monoisotopic): 456.1685

AlogP: 3.89

#Rotatable Bonds: 9

Polar Surface Area: 111.10

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.59

CX Basic pKa:

CX LogP: 4.10

CX LogD: 0.75

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.29

Np Likeness Score: -0.44

References

1. Hagishita S, Yamada M, Shirahase K, Okada T, Murakami Y, Ito Y, Matsuura T, Wada M, Kato T, Ueno M, Chikazawa Y, Yamada K, Ono T, Teshirogi I, Ohtani M..  (1996)  Potent inhibitors of secretory phospholipase A2: synthesis and inhibitory activities of indolizine and indene derivatives.,  39  (19): [PMID:8809154] [10.1021/jm960395q]

2. Oslund RC, Cermak N, Gelb MH..  (2008)  Highly specific and broadly potent inhibitors of mammalian secreted phospholipases A2.,  51  (15): [PMID:18605714] [10.1021/jm800422v]

3. Robello M, Barresi E, Baglini E, Salerno S, Taliani S, Settimo FD..  (2021)  The Alpha Keto Amide Moiety as a Privileged Motif in Medicinal Chemistry: Current Insights and Emerging Opportunities.,  64  (7.0): [PMID:33764065] [10.1021/acs.jmedchem.0c01808]

Source

Source(1):

• Scientific Literature