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stemphyloxin II

Go to external page http://purl.obolibrary.org/obo/CHEBI_145066

A carbotricyclic compound that is betaenone A in which the butan-2-yl side-chain has been hydroxylated at position 1. A phytotoxin isolated from the endophytic fungus Stemphylium botryosum, it shows high affinity for ferric (but not ferrous) ions.

Term info

Label

stemphyloxin II

Synonyms
  • (1S,2S,4R,6R,7S,8R,10Z,11S,12R)-1,4,11-trihydroxy-12-[(2R)-1-hydroxybutan-2-yl]-10-(hydroxymethylene)-4,6,8,11-tetramethyltricyclo[6.2.2.0(2,7)]dodecan-9-one
database cross reference
Subsets

3_STAR

IUPAC NAME
(1S,2S,4R,6R,7S,8R,10Z,11S,12R)-1,4,11-trihydroxy-12-[(2R)-1-hydroxybutan-2-yl]-10-(hydroxymethylene)-4,6,8,11-tetramethyltricyclo[6.2.2.0(2,7)]dodecan-9-one [ IUPAC ]

charge

0

formula

C21H34O6

has obo namespace

chebi_ontology

has related synonym

(1R,3Z,4S,4aS,6R,8R,8aS,9S,10R)-4,6,9-trihydroxy-10-[(2R)-1-hydroxybutan-2-yl]-3-(hydroxymethylidene)-1,6,8,9-tetramethyloctahydro-1,4-ethanonaphthalen-2(1H)-one

id

CHEBI:145066

inchi

InChI=1S/C21H34O6/c1-6-12(9-22)16-19(4)15-11(2)7-18(3,25)8-13(15)21(27,20(16,5)26)14(10-23)17(19)24/h10-13,15-16,22-23,25-27H,6-9H2,1-5H3/b14-10+/t11-,12+,13+,15+,16-,18-,19-,20+,21+/m1/s1

inchikey

JTFGPTHCAAUOQL-RNPLJHCFSA-N

mass

382.497

monoisotopicmass

382.23554

smiles

[C@]12(C(/C(/[C@]([C@@]3([C@@]1([C@@](C[C@](C3)(O)C)(C)[H])[H])[H])(O)[C@@]([C@@]2([C@@H](CC)CO)[H])(C)O)=C\O)=O)C