pentalenolactone (CHEBI:70816)

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ChEBI Name	pentalenolactone

ChEBI ID	CHEBI:70816

Definition	A sesquiterpene lactone that is isolated from several Streptomyces species and exhibits antibiotic activity.

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

Supplier Information

Download	Molfile XML SDF

Formula

C15H16O5

Net Charge

Average Mass

276.28450

Monoisotopic Mass

276.09977

InChI

InChI=1S/C15H16O5/c1-7-4-14-10(8(7)2)3-9(12(16)17)11(14)5-19-13(18)15(14)6-20-15/h3-4,8,10-11H,5-6H2,1-2H3,(H,16,17)/t8-,10-,11+,14-,15-/m1/s1

InChIKey

NUPNVWUYFVEAIT-UJJBCWTCSA-N

SMILES

[H][C@@]12COC(=O)[C@]3(CO3)[C@@]11C=C(C)[C@@H](C)[C@@]1([H])C=C2C(O)=O

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):	antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. EC 1.2.1.12 [glyceraldehyde-3-phosphate dehydrogenase (phosphorylating)] inhibitor An EC 1.2.1.* (oxidoreductase acting on donor aldehyde/oxo group with NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of glyceraldehyde-3-phosphate dehydrogenase (EC 1.2.1.12). bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria.

ChEBI Ontology
Outgoing	pentalenolactone (CHEBI:70816) has role antimicrobial agent (CHEBI:33281) pentalenolactone (CHEBI:70816) has role bacterial metabolite (CHEBI:76969) pentalenolactone (CHEBI:70816) has role EC 1.2.1.12 [glyceraldehyde-3-phosphate dehydrogenase (phosphorylating)] inhibitor (CHEBI:70817) pentalenolactone (CHEBI:70816) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020) pentalenolactone (CHEBI:70816) is a organic heterotricyclic compound (CHEBI:26979) pentalenolactone (CHEBI:70816) is a sesquiterpene lactone (CHEBI:37667) pentalenolactone (CHEBI:70816) is a spiro-epoxide (CHEBI:133131) pentalenolactone (CHEBI:70816) is conjugate acid of pentalenolactone(1−) (CHEBI:70790)

Incoming	pentalenolactone(1−) (CHEBI:70790) is conjugate base of pentalenolactone (CHEBI:70816)

IUPAC Name

(2R,4a'S,7'S,7a'R,9a'R)-6',7'-dimethyl-3'-oxo-1',7',7a',9a'-tetrahydrospiro[oxirane-2,4'-pentaleno[1,6a-c]pyran]-9'-carboxylic acid

Last Modified

24 August 2016