(+)-Alantolactone
Basic information
- CAS
1407-14-3- Standard SMILES
C=C1C(=O)O[C@@H]2C[C@@]3(C)CCC[C@H](C)C3=C[C@H]12- InChIKey
PXOYOCNNSUAQNS-AGNJHWRGSA-N- Molecular formula
- C15H20O2
- Average molar mass
- 232.32 g/mol
- Monoisotopic mass
- 232.14632988
Overview
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.
Names & identifiers
- Preferred name
- (+)-Alantolactone
- IUPAC
- (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
Names & synonyms
Alantolactone546-43-0EupatalAlant camphorInula camphorElecampane camphorDTXSID90877864M7GSN5Q1M6CHEBI:2540NSC-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)-oneNSC-333843
Show more names
(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-oneRefChem:110486DTXCID701015930208-899-3(+)-Alantolactonehelenine
Database identifiers
- CAS
1407-14-3、546-43-0- PubChem CID
- 72724
- DTXSID
DTXSID90877864- ChEMBL
CHEMBL136356- ChEBI
CHEBI:2540- UNII
- M7GSN5Q1M6
- EC Number
- 208-899-3、215-803-3
- Nikkaji
- J13.573I
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 421
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]
LogP3.38
Collision Cross Section
153.87 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
149.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Sens. 1 (100%)
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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