CHEBI:5635 - helenalin

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ChEBI Name helenalin
ChEBI ID CHEBI:5635
Definition A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C15H18O4
Net Charge 0
Average Mass 262.30100
Monoisotopic Mass 262.121
InChI InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1
InChIKey ZVLOPMNVFLSSAA-XEPQRQSNSA-N
SMILES C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2[C@H](O)[C@@]2(C)[C@H]1C=CC2=O
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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing helenalin (CHEBI:5635) has role anti-inflammatory agent (CHEBI:67079)
helenalin (CHEBI:5635) has role antineoplastic agent (CHEBI:35610)
helenalin (CHEBI:5635) has role metabolite (CHEBI:25212)
helenalin (CHEBI:5635) has role plant metabolite (CHEBI:76924)
helenalin (CHEBI:5635) is a γ-lactone (CHEBI:37581)
helenalin (CHEBI:5635) is a cyclic ketone (CHEBI:3992)
helenalin (CHEBI:5635) is a organic heterotricyclic compound (CHEBI:26979)
helenalin (CHEBI:5635) is a secondary alcohol (CHEBI:35681)
helenalin (CHEBI:5635) is a sesquiterpene lactone (CHEBI:37667)
IUPAC Name
(3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
Synonyms Sources
(3aS)-3,3aα,4α,4a,7aα,8,9,9aα-octahydro-4-hydroxy-4aβ,8α-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione ChemIDplus
6α,8β-dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone ChemIDplus
Helenalin A ChemIDplus
Manual Xrefs Databases
C00003298 KNApSAcK
C09473 KEGG COMPOUND
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Registry Numbers Types Sources
28081 Reaxys Registry Number Reaxys
6754-13-8 CAS Registry Number KEGG COMPOUND
6754-13-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
20175984 PubMed citation Europe PMC
21669190 PubMed citation Europe PMC
22784363 PubMed citation Europe PMC
23123298 PubMed citation Europe PMC
23727063 PubMed citation Europe PMC
24044884 PubMed citation Europe PMC
Last Modified
28 July 2014