3-(3-Carboxypropanoyl)-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-5-carboxylic acid

ID: ALA1801024

Chembl Id: CHEMBL1801024

PubChem CID: 25230917

Max Phase: Preclinical

Molecular Formula: C30H35NO7

Molecular Weight: 521.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCc1ccc(OCC(=O)Cn2cc(C(=O)CCC(=O)O)c3cc(C(=O)O)ccc32)cc1

Standard InChI:  InChI=1S/C30H35NO7/c1-2-3-4-5-6-7-8-21-9-12-24(13-10-21)38-20-23(32)18-31-19-26(28(33)15-16-29(34)35)25-17-22(30(36)37)11-14-27(25)31/h9-14,17,19H,2-8,15-16,18,20H2,1H3,(H,34,35)(H,36,37)

Standard InChI Key:  CILKLAAENJJNEQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1801024

   3-(3-Carboxypropanoyl)-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-5-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: 521.61

Molecular Weight (Monoisotopic): 521.2414

AlogP: 5.94

#Rotatable Bonds: 17

Polar Surface Area: 122.90

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.37

CX Basic pKa: ┄

CX LogP: 6.29

CX LogD: -0.15

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.17

Np Likeness Score: -0.37

References

1. Bovens S, Schulze Elfringhoff A, Kaptur M, Reinhardt D, Schäfers M, Lehr M..  (2010)  1-(5-Carboxyindol-1-yl)propan-2-one inhibitors of human cytosolic phospholipase A2α: effect of substituents in position 3 of the indole scaffold on inhibitory potency, metabolic stability, solubility, and bioavailability.,  53  (23): [PMID:21067218] [10.1021/jm101094p]

2. Arnsmann M, Hanekamp W, Elfringhoff AS, Lehr M..  (2017)  Structure-activity relationship studies on 1-(2-oxopropyl)indole-5-carboxylic acids acting as inhibitors of cytosolic phospholipase A2α: Effect of substituents at the indole 3-position on activity, solubility, and metabolic stability.,  125  [PMID:27810597] [10.1016/j.ejmech.2016.10.039]

Source

Source(1):

• Scientific Literature