(1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol (CHEBI:66168)

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ChEBI Name	(1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol

ChEBI ID	CHEBI:66168

ChEBI ASCII Name	(1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol

Definition	A germacrane sesquiterpenoid that is 4,5-epoxygermacra-9Z-ene substituted by hydroxy groups at positions 1, 2 and 6. Isolated from Santolina insularis, it exhibits cytotoxicity against human colon carcinoma cell line.

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

Supplier Information

Download	Molfile XML SDF

Formula

C15H26O4

Net Charge

Average Mass

270.36450

Monoisotopic Mass

270.18311

InChI

InChI=1S/C15H26O4/c1-8(2)10-6-5-9(3)12(17)11(16)7-15(4)14(19-15)13(10)18/h5,8,10-14,16-18H,6-7H2,1-4H3/b9-5-/t10-,11+,12+,13+,14-,15-/m0/s1

InChIKey

UOUMJKKOPWRYPB-QBCLFKMJSA-N

SMILES

[H][C@@]12O[C@@]1(C)C[C@@H](O)[C@H](O)\C(C)=C/C[C@@H](C(C)C)[C@H]2O

Metabolite of Species	Details
Santolina insularis (NCBI:txid765941)	Found in aerial part (BTO:0001658). See: PubMed

Roles Classification
Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	(1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol (CHEBI:66168) has role antineoplastic agent (CHEBI:35610) (1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol (CHEBI:66168) has role metabolite (CHEBI:25212) (1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol (CHEBI:66168) is a epoxide (CHEBI:32955) (1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol (CHEBI:66168) is a germacrane sesquiterpenoid (CHEBI:68588) (1R,2R,4S,5S,6R,7S)4,5-epoxygermacra-9Z-en-1,2,6-triol (CHEBI:66168) is a triol (CHEBI:27136)

IUPAC Name

(1S,2R,3S,5Z,7R,8R,10S)-6,10-dimethyl-3-(propan-2-yl)-11-oxabicyclo[8.1.0]undec-5-ene-2,7,8-triol

Registry Number	Type	Source
15769284	Reaxys Registry Number	Reaxys

Citation	Type	Source
15974607	PubMed citation	Europe PMC

Last Modified

25 September 2013