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

ID: ALA1800992

Chembl Id: CHEMBL1800992

PubChem CID: 49851262

Max Phase: Preclinical

Molecular Formula: C32H41NO5

Molecular Weight: 519.68

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C32H41NO5/c1-3-5-7-8-9-11-12-24-14-17-27(18-15-24)38-23-26(34)21-33-22-29(31(35)13-10-6-4-2)28-20-25(32(36)37)16-19-30(28)33/h14-20,22H,3-13,21,23H2,1-2H3,(H,36,37)

Standard InChI Key:  XCMKIPBGIUPMSH-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1800992

   3-Hexanoyl-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: 519.68

Molecular Weight (Monoisotopic): 519.2985

AlogP: 7.65

#Rotatable Bonds: 18

Polar Surface Area: 85.60

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.63

CX Basic pKa: ┄

CX LogP: 8.50

CX LogD: 5.16

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.14

Np Likeness Score: -0.35

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