4-Oxo-8-[3-(4-pentyl-phenyl)-acryloylamino]-4H-chromene-2-carboxylic acid

ID: ALA174483

Chembl Id: CHEMBL174483

PubChem CID: 13997664

Max Phase: Preclinical

Molecular Formula: C24H23NO5

Molecular Weight: 405.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCc1ccc(/C=C/C(=O)Nc2cccc3c(=O)cc(C(=O)O)oc23)cc1

Standard InChI:  InChI=1S/C24H23NO5/c1-2-3-4-6-16-9-11-17(12-10-16)13-14-22(27)25-19-8-5-7-18-20(26)15-21(24(28)29)30-23(18)19/h5,7-15H,2-4,6H2,1H3,(H,25,27)(H,28,29)/b14-13+

Standard InChI Key:  HUNHHUAGWDAVDL-BUHFOSPRSA-N

Alternative Forms

1. Parent:

   

   ALA174483

   4-oxo-8-[[(E)-3-(4-pentylphenyl)prop-2-enoyl]amino]chromene-2-carboxylic 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: 405.45

Molecular Weight (Monoisotopic): 405.1576

AlogP: 4.88

#Rotatable Bonds: 8

Polar Surface Area: 96.61

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.04

CX Basic pKa: ┄

CX LogP: 5.19

CX LogD: 1.66

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.41

Np Likeness Score: -0.08

References

1. Nakai H, Konno M, Kosuge S, Sakuyama S, Toda M, Arai Y, Obata T, Katsube N, Miyamoto T, Okegawa T..  (1988)  New potent antagonists of leukotrienes C4 and D4. 1. Synthesis and structure-activity relationships.,  31  (1): [PMID:3336036] [10.1021/jm00396a013]

2. Proschak E, Heitel P, Kalinowsky L, Merk D..  (2017)  Opportunities and Challenges for Fatty Acid Mimetics in Drug Discovery.,  60  (13): [PMID:28252961] [10.1021/acs.jmedchem.6b01287]

Source

Source(1):

• Scientific Literature