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

ID: ALA205892

Chembl Id: CHEMBL205892

Cas Number: 741605-76-5

PubChem CID: 11690325

Max Phase: Preclinical

Molecular Formula: C26H31NO4

Molecular Weight: 421.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCc1ccc(OCC(=O)Cn2ccc3cc(C(=O)O)ccc32)cc1

Standard InChI:  InChI=1S/C26H31NO4/c1-2-3-4-5-6-7-8-20-9-12-24(13-10-20)31-19-23(28)18-27-16-15-21-17-22(26(29)30)11-14-25(21)27/h9-17H,2-8,18-19H2,1H3,(H,29,30)

Standard InChI Key:  QGRRJJFZKZREIR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA205892

   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: 421.54

Molecular Weight (Monoisotopic): 421.2253

AlogP: 5.89

#Rotatable Bonds: 13

Polar Surface Area: 68.53

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.63

CX Basic pKa: ┄

CX LogP: 6.90

CX LogD: 3.57

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: -0.44

References

1. Ludwig J, Bovens S, Brauch C, Elfringhoff AS, Lehr M..  (2006)  Design and synthesis of 1-indol-1-yl-propan-2-ones as inhibitors of human cytosolic phospholipase A2alpha.,  49  (8): [PMID:16610804] [10.1021/jm051243a]

2. Hess M, Schulze Elfringhoff A, Lehr M..  (2007)  1-(5-Carboxy- and 5-carbamoylindol-1-yl)propan-2-ones as inhibitors of human cytosolic phospholipase A2alpha: bioisosteric replacement of the carboxylic acid and carboxamide moiety.,  15  (8): [PMID:17320401] [10.1016/j.bmc.2007.02.016]

3. Fritsche A, Elfringhoff AS, Fabian J, Lehr M..  (2008)  1-(2-Carboxyindol-5-yloxy)propan-2-ones as inhibitors of human cytosolic phospholipase A2alpha: synthesis, biological activity, metabolic stability, and solubility.,  16  (7): [PMID:18321717] [10.1016/j.bmc.2008.02.019]

4. Bovens S, Kaptur M, Elfringhoff AS, Lehr M..  (2009)  1-(5-Carboxyindol-1-yl)propan-2-ones as inhibitors of human cytosolic phospholipase A2alpha: synthesis and properties of bioisosteric benzimidazole, benzotriazole and indazole analogues.,  19  (8): [PMID:19327988] [10.1016/j.bmcl.2009.03.019]

5. Forster L, Ludwig J, Kaptur M, Bovens S, Elfringhoff AS, Holtfrerich A, Lehr M..  (2010)  1-Indol-1-yl-propan-2-ones and related heterocyclic compounds as dual inhibitors of cytosolic phospholipase A(2)alpha and fatty acid amide hydrolase.,  18  (2): [PMID:20005725] [10.1016/j.bmc.2009.11.028]

6. Drews A, Bovens S, Roebrock K, Sunderkötter C, Reinhardt D, Schäfers M, van der Velde A, Schulze Elfringhoff A, Fabian J, Lehr M..  (2010)  1-(5-carboxyindol-1-yl)propan-2-one inhibitors of human cytosolic phospholipase A(2)alpha with reduced lipophilicity: synthesis, biological activity, metabolic stability, solubility, bioavailability, and topical in vivo activity.,  53  (14): [PMID:20583844] [10.1021/jm1001088]

7. Kaptur M, Elfringhoff AS, Lehr M..  (2011)  Structure-activity relationship studies on 1-(5-carboxyindol-1-yl)-propan-2-one inhibitors of human cytosolic phospholipase A2α: variation of the activated ketone moiety.,  21  (6): [PMID:21316224] [10.1016/j.bmcl.2011.01.085]

8. 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