CHEBI:46971 - premnaspirodiene

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ChEBI Name premnaspirodiene
ChEBI ID CHEBI:46971
Definition A spiro compound that is vetispirane that has been dehydrogenated to introduce a double bond position 6-7 and in which the isopropyl subsbstituent has been replaced by a prop-1-en-2-yl group (the 2R,5S,10R isomer).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:32294, CHEBI:27285
Supplier Information
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Formulae C15H24
C15H24
Net Charge 0
Average Mass 204.35110
Monoisotopic Mass 204.18780
InChI InChI=1S/C15H24/c1-11(2)14-8-9-15(10-14)12(3)6-5-7-13(15)4/h6,13-14H,1,5,7-10H2,2-4H3/t13-,14-,15-/m1/s1
InChIKey WEZDOYDDKIHCLM-RBSFLKMASA-N
SMILES C[C@@H]1CCC=C(C)[C@]11CC[C@H](C1)C(C)=C
Metabolite of Species Details
Vernonia cinerea (IPNI:1164899-2) See: South African Journal of Botany. 2014, 95, 129-130
Hyoscyamus muticus (NCBI:txid35626) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing premnaspirodiene (CHEBI:46971) has parent hydride vetispirane (CHEBI:36754)
premnaspirodiene (CHEBI:46971) has role plant metabolite (CHEBI:76924)
premnaspirodiene (CHEBI:46971) is a sesquiterpene (CHEBI:35189)
premnaspirodiene (CHEBI:46971) is a spiro compound (CHEBI:33599)
IUPAC Name
(2R,5S,10R)-6,10-dimethyl-2-(prop-1-en-2-yl)spiro[4.5]dec-6-ene
Synonyms Sources
(−)-premnaspirodiene ChEBI
(−)-vetispiradiene UniProt
(−)-vetispiradiene ChEBI
Manual Xrefs Databases
6BW PDBeChem
C00007637 KNApSAcK
C12142 KEGG COMPOUND
CPD-4703 MetaCyc
LMPR0103650003 LIPID MAPS
View more database links
Citations Waiting for Citations Types Sources
12504906 PubMed citation Europe PMC
16309622 PubMed citation Europe PMC
17715131 PubMed citation Europe PMC
25788404 PubMed citation Europe PMC
27328867 PubMed citation Europe PMC
7706281 PubMed citation Europe PMC
IND605414758 Agricola citation Europe PMC
Last Modified
12 April 2018
General Comment
2011-03-09 Vetispirodiene was initially thought to be the (2S,5S,10R)-diastereomer, but was subsequently found to be the same as premnaspirodiene, with (2R,5S,10R) stereochemistry. [PMID 12504906]