Compound: HELENALIN
SMILES: O=C1O[C@@H]2C[C@H]([C@@H]3C=CC([C@]3([C@H]([C@@H]2C1=C)O)C)=O)C
InChIKey: ZVLOPMNVFLSSAA-XEPQRQSNSA-N
Synonyms: HELENALIN, 6754-13-8, Helenalin A, PF 56, 4GUY9L896T, NSC-85236, 6alpha,8beta-Dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone, CHEBI:5635, (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione, DTXSID50217868, Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone, (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione, Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-, (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno(6,7-b)furan-2,8-dione, (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno(6,7-b)furan-2,8-dione, RefChem:145455, DTXCID00140359, HSDB 3490, NSC85236, NSC 85236, MLS000728512, Ambrosa-2,11(13)-dien-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone, SMR000445626, (3aR,5R,5aR,8aR,9S,9aS)-9-Hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[7,6-d]furan-2,8-dione, (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, MLS002701927, BRN 0028081, UNII-4GUY9L896T, NF-kappaB inhibitor, HELENALIN [MI], HELENALIN [HSDB], (-)-HELENALIN, BSPBio_001312, (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-Octahydro-4-hydroxy-4abeta,8 alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione, 4-18-00-01434 (Beilstein Handbook Reference), cid_23205, SCHEMBL161593, CHEMBL338474, orb1707223, BDBM43484, HMS1791B14, HMS1989B14, HMS2236C04, EX-A10269, HB3927, MFCD01674580, AKOS040741831, Ambrosa-2,11(13)-dien-12-oic acid, 6.alpha.,8.beta.-dihydroxy-4-oxo-, 12,8-lactone, NCGC00163416-01, NCGC00163416-02, Azuleno[6,5-b]furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, [3aS-(3a.alpha.,4.alpha.,4a.beta.,7a.alpha.,8.alpha.,9a.alpha.)]-, FH177939, MS-23694, NCI60_041870, HY-119970, CS-0078850, NS00094722, C09473, G13013, Q387505, WLN: T C575 DYVO MV KUTJ A1 BQ DU1 I1, BRD-K26302255-001-02-3, Ambrosa-2, 6.alpha.,8.beta.-dihydroxy-4-oxo-, 12,8-lactone, 6.ALPHA.,8.BETA.-DIHYDROXY-4-OXOAMBROSA-2,11(13)-DIEN-12-OIC ACID 12,8-LACTONE, (3aR,5R,5aR,8aR,9S,9aS)-5,8a-dimethyl-1-methylidene-9-oxidanyl-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione, (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-quinone, (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-octahydro-4-hydroxy-4abeta,8alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione, (3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione, (3AS-(3A.ALPHA.,4.ALPHA.,4A.BETA.,7A.ALPHA.,8.ALPHA.,9A.ALPHA.))-3,3A,4,4A,7A,8,9,9A-OCTAHYDRO-4-HYDROXY-4A,8-DIMETHYL-3-METHYLENEAZULENO(6,5-B)FURAN-2,5-DIONE, 4-Hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione, Azuleno[6,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, [3aS-(3a.alpha.,4.alpha.,4a.beta.,7a.alpha.,8.alpha.,9a.alpha.)]-
Theoretical properties:
molecular_formula: C15H18O4
molecular_weight: 262.30 g/mol
exact_mass: 262.12050905 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 19
topological_polar_surface_area: 63.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: STERNUTATIVE CRYSTALS FROM BENZENE
color: STERNUTATIVE CRYSTALS FROM BENZENE
melting_point: 167-168 °C
solubility: SLIGHTLY SOL IN WATER; SOL IN ALCOHOL, CHLOROFORM, HOT BENZENE
Descriptions:
pubchem: Helenalin is 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). It has a role as a metabolite, an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is an organic heterotricyclic compound, a secondary alcohol, a gamma-lactone, a sesquiterpene lactone and a cyclic ketone.
chebi: A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-<em>b</em>]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 3a<i>S</i>,4<i>S</i>,4a<i>R</i>,7a<i>R</i>,8<i>R</i>,9a<i>R</i> stereoisomer).
chembl: HELENALIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Helenalin, or (-)-4-Hydroxy-4a,8-dimethyl-3,3a,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione, is a toxic sesquiterpene lactone which can be found in several plants such as Arnica montana and Arnica chamissonis Helenalin is responsible for the toxicity of the Arnica spp. 
Although toxic, helenalin possesses some in vitro anti-inflammatory and anti-neoplastic effects. Helenalin can inhibit certain enzymes, such as 5-lipoxygenase and leukotriene C4 synthase. For this reason the compound or its derivatives may have potential medical applications.