varespladib (CHEBI:189668)

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ChEBI Name	varespladib

ChEBI ID	CHEBI:189668

Definition	A member of the class of indoles that is 1H-indole substituted by benzyl, ethyl, oxamoyl, and carboxymethoxy groups at positions 1, 2, 3, and 4, respectively. It is an oral secretory phospholipase A₂ inhibitor and exhibits anti-inflammatory effects.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C21H20N2O5

Net Charge

Average Mass

380.400

Monoisotopic Mass

380.13722

InChI

InChI=1S/C21H20N2O5/c1-2-14-19(20(26)21(22)27)18-15(9-6-10-16(18)28-12-17(24)25)23(14)11-13-7-4-3-5-8-13/h3-10H,2,11-12H2,1H3,(H2,22,27)(H,24,25)

InChIKey

BHLXTPHDSZUFHR-UHFFFAOYSA-N

SMILES

CCC1=C(C(=O)C(N)=O)C2=C(OCC(O)=O)C=CC=C2N1CC1=CC=CC=C1

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	EC 3.1.1.4 (phospholipase A2) inhibitor An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of phospholipase A2 (EC 3.1.1.4).

Application(s):	anti-inflammatory drug A substance that reduces or suppresses inflammation. antidote Any protective agent counteracting or neutralizing the action of poisons.

ChEBI Ontology
Outgoing	varespladib (CHEBI:189668) has role anti-inflammatory drug (CHEBI:35472) varespladib (CHEBI:189668) has role antidote (CHEBI:50247) varespladib (CHEBI:189668) has role EC 3.1.1.4 (phospholipase A₂) inhibitor (CHEBI:50469) varespladib (CHEBI:189668) is a aromatic ether (CHEBI:35618) varespladib (CHEBI:189668) is a benzenes (CHEBI:22712) varespladib (CHEBI:189668) is a dicarboxylic acid monoamide (CHEBI:35735) varespladib (CHEBI:189668) is a indoles (CHEBI:24828) varespladib (CHEBI:189668) is a monocarboxylic acid (CHEBI:25384) varespladib (CHEBI:189668) is a primary carboxamide (CHEBI:140324) varespladib (CHEBI:189668) is conjugate acid of varespladib(1−) (CHEBI:189666)

Incoming	varespladib methyl (CHEBI:192805) has functional parent varespladib (CHEBI:189668) varespladib(1−) (CHEBI:189666) is conjugate base of varespladib (CHEBI:189668)

IUPAC Name

({3-[amino(oxo)acetyl]-1-benzyl-2-ethyl-1H-indol-4-yl}oxy)acetic acid

Synonyms	Sources
2-[2-ethyl-3-oxamoyl-1-(phenylmethyl)indol-4-yl]oxyethanoic acid	PDBeChem
2-[[3-(2-Amino-2-oxoacetyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid	ChEBI
A-001	ChEBI
LY 315920	ChEBI
LY-315920	ChEBI
LY315920	ChemIDplus
S 5920	ChemIDplus
S-5920	ChemIDplus

Registry Number	Type	Source
172732-68-2	CAS Registry Number	ChemIDplus

Last Modified

04 August 2022