Compound: Alantolactone
SMILES: O=C1O[C@@H]2C[C@]3(CCC[C@@H](C3=C[C@@H]2C1=C)C)C
InChIKey: PXOYOCNNSUAQNS-AGNJHWRGSA-N
Synonyms: Alantolactone, 546-43-0, Eupatal, Alant camphor, Inula camphor, Elecampane camphor, M7GSN5Q1M6, CHEBI:2540, DTXSID90877864, NSC-93131, (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one, NSC-333843, (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one, (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-3a,5,6,7,8,8a,9,9a-octahydronaphtho(2,3-b)furan-2(3H)-one, (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo(f)(1)benzofuran-2-one, RefChem:110486, DTXCID701015930, 208-899-3, (+)-Alantolactone, helenine, helenin, (3aR,5S,8aR,9aR)-5,8a-Dimethyl-3-methylene-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one, AI3-31147, NSC93131, CHEMBL136356, Naphtho[2,3-b]furan-2(3H)-one,3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-,(3aR,5S,8aR,9aR)-, (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f]benzofuran-2-one, MFCD00274568, EINECS 208-899-3, NSC 93131, UNII-M7GSN5Q1M6, NSC 302289, PXOYOCNNSUAQNS-AGNJHWRGSA-N, Spectrum_000297, (+)-Alantolactone; Alant camphor; Inula camphor, Alantolactone (Standard), Spectrum2_000297, Spectrum3_001358, Spectrum4_001772, Spectrum5_000383, ALANTOLACTONE [MI], Epitope ID:119691, BSPBio_003175, KBioGR_002284, KBioSS_000777, SPECTRUM310010, SCHEMBL155169, SPBio_000234, orb1304877, orb3140705, HY-N0038R, KBio2_000777, KBio2_003345, KBio2_005913, KBio3_002395, Alantolactone, >=98% (HPLC), GLXC-02854, HY-N0038, BDBM50096873, CCG-39639, s8318, 4alphaH-Eudesma-5,11(13)-dien-12-oic acid, 8beta-hydroxy-, gamma-lactone, AKOS015906135, CS-3595, EBC-465079, FA65639, LMPR0103190013, SDCCGMLS-0066583.P001, NCGC00178225-01, NCGC00178225-02, NCGC00178225-05, (3aR,5S,8aR,9aR)-3a,5,6,7,8,8a,9,9a-Octahydro-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one, (3AR,5S,8AR,9AR)-5,8A-DIMETHYL-3-METHYLIDENE-2H,3H,3AH,5H,6H,7H,8H,8AH,9H,9AH-NAPHTHO[2,3-B]FURAN-2-ONE, (3AR-(3aalpha,5beta,8abeta,9aalpha))-3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylenenaphtho(2,3-b)furan-2(3H)-one, AC-31414, BS-17042, Naphtho(2,3-b)furan-2(3H)-one, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, (3aR-(3a alpha,5beta,8a beta,9a alpha))-, NCI60_042073, C09289, Q21099633, 4.alpha.H-Eudesma-5, 8.beta.-hydroxy-, .gamma.-lactone, 8.BETA.-HYDROXY-4.ALPHA.H-EUDESM-5-EN-12-OIC ACID .GAMMA.-LACTONE, [3aR-(3a alpha,5 beta,8a beta,9a alpha)]-3a,5,6,7,8,8a,9,9a-Octahydro-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one, Naphtho[2, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, [3aR-(3a.alpha.,5.beta.,8a.beta.,9a.alpha.)]-, Naphtho[2,3-b]furan-2(3H)-one, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, (3aR,5S,8aR,9aR)-
Theoretical properties:
molecular_formula: C15H20O2
molecular_weight: 232.32 g/mol
exact_mass: 232.146329876 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 17
topological_polar_surface_area: 26.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Alantolactone is a sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3. It has a role as an antineoplastic agent, an apoptosis inducer and a plant metabolite. It is a sesquiterpene lactone, a naphthofuran and an olefinic compound.
chebi: A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-<em>b</em>]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3.
chembl: HELENINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Helenin is a phytochemical mixture found in many plant species, including the Inula helenium (elecampane) of the family Asteraceae.  It is a mixture of two isomeric sesquiterpene lactones, alantolactone and isoalantolactone.
In 1895 the German scientists Julius Bredt and Wilhelm Posh extracted helenin from Inula helenium and determined its physical and chemical properties.