4-(5-Cyclopentyloxycarbonylamino-1-methyl-1H-indol-3-ylmethyl)-3-methoxy-benzoic acid

ID: ALA298727

Chembl Id: CHEMBL298727

Cas Number: 107754-20-1

PubChem CID: 11293119

Max Phase: Preclinical

Molecular Formula: C24H26N2O5

Molecular Weight: 422.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)O)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12

Standard InChI:  InChI=1S/C24H26N2O5/c1-26-14-17(11-15-7-8-16(23(27)28)12-22(15)30-2)20-13-18(9-10-21(20)26)25-24(29)31-19-5-3-4-6-19/h7-10,12-14,19H,3-6,11H2,1-2H3,(H,25,29)(H,27,28)

Standard InChI Key:  KFQBKNCZRCRBOU-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA298727

   4-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic 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: 422.48

Molecular Weight (Monoisotopic): 422.1842

AlogP: 4.97

#Rotatable Bonds: 6

Polar Surface Area: 89.79

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.98

CX Basic pKa: ┄

CX LogP: 5.10

CX LogD: 1.93

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.59

Np Likeness Score: -0.47

References

1. Matassa VG, Maduskuie TP, Shapiro HS, Hesp B, Snyder DW, Aharony D, Krell RD, Keith RA..  (1990)  Evolution of a series of peptidoleukotriene antagonists: synthesis and structure/activity relationships of 1,3,5-substituted indoles and indazoles.,  33  (6): [PMID:2342072] [10.1021/jm00168a037]

2. Brown FJ, Cronk LA, Aharony D, Snyder DW..  (1992)  1,3,6-trisubstituted indoles as peptidoleukotriene antagonists: benefits of a second, polar, pyrrole substituent.,  35  (13): [PMID:1320123] [10.1021/jm00091a010]

3. 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