(3-Aminooxalyl-1-benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid

ID: ALA346196

Chembl Id: CHEMBL346196

PubChem CID: 9863966

Max Phase: Preclinical

Molecular Formula: C20H18N2O5

Molecular Weight: 366.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccccc1

Standard InChI:  InChI=1S/C20H18N2O5/c1-12-17(19(25)20(21)26)18-14(8-5-9-15(18)27-11-16(23)24)22(12)10-13-6-3-2-4-7-13/h2-9H,10-11H2,1H3,(H2,21,26)(H,23,24)

Standard InChI Key:  FBGWHCFPQBQYNU-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA346196

   ((3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetic 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: 366.37

Molecular Weight (Monoisotopic): 366.1216

AlogP: 2.13

#Rotatable Bonds: 7

Polar Surface Area: 111.62

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.56

CX Basic pKa: ┄

CX LogP: 2.25

CX LogD: -1.11

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: -0.78

References

1. Draheim SE, Bach NJ, Dillard RD, Berry DR, Carlson DG, Chirgadze NY, Clawson DK, Hartley LW, Johnson LM, Jones ND, McKinney ER, Mihelich ED, Olkowski JL, Schevitz RW, Smith AC, Snyder DW, Sommers CD, Wery JP..  (1996)  Indole inhibitors of human nonpancreatic secretory phospholipase A2. 3. Indole-3-glyoxamides.,  39  (26): [PMID:8978844] [10.1021/jm960487f]

2. Smart BP, Oslund RC, Walsh LA, Gelb MH..  (2006)  The first potent inhibitor of mammalian group X secreted phospholipase A2: elucidation of sites for enhanced binding.,  49  (10): [PMID:16686528] [10.1021/jm060136t]

3. Robello M, Barresi E, Baglini E, Salerno S, Taliani S, Settimo FD..  (2021)  The Alpha Keto Amide Moiety as a Privileged Motif in Medicinal Chemistry: Current Insights and Emerging Opportunities.,  64  (7.0): [PMID:33764065] [10.1021/acs.jmedchem.0c01808]

Source

Source(1):

• Scientific Literature