3-isobutyryl-1-(3-(4-octylphenoxy)-2-oxopropyl)-1H-indole-5-carboxylic acid

ID: ALA4097068

Chembl Id: CHEMBL4097068

PubChem CID: 49851263

Max Phase: Preclinical

Molecular Formula: C30H37NO5

Molecular Weight: 491.63

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C30H37NO5/c1-4-5-6-7-8-9-10-22-11-14-25(15-12-22)36-20-24(32)18-31-19-27(29(33)21(2)3)26-17-23(30(34)35)13-16-28(26)31/h11-17,19,21H,4-10,18,20H2,1-3H3,(H,34,35)

Standard InChI Key:  BFSRCVAMCRMHBI-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4097068

   3-(2-Methylpropanoyl)-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: 491.63

Molecular Weight (Monoisotopic): 491.2672

AlogP: 6.73

#Rotatable Bonds: 15

Polar Surface Area: 85.60

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.63

CX Basic pKa: ┄

CX LogP: 7.70

CX LogD: 4.37

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.19

Np Likeness Score: -0.29

References

1. 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]

2. Subeska A, Althaus J, Hake T, Hanekamp W, Bettenworth D, Mulac D, Langer K, Lehr M..  (2023)  Synthesis and pharmacokinetic properties of novel cPLA₂α inhibitors with 1-(carboxyalkylpyrrolyl)-3-aryloxypropan-2-one structure.,  77  [PMID:36495814] [10.1016/j.bmc.2022.117110]

Source

Source(1):

• Scientific Literature