(3aS,5aR,9R,9aS,9bS)-Decahydro-9-hydroxy-5a,9-dimethyl-3-methylenenaphtho(1,2-b)furan-2(3H)-one
Basic information
- CAS
27652-22-8- Standard SMILES
C=C1C(=O)O[C@@H]2[C@@H]3[C@](C)(CCC[C@@]3(C)O)CC[C@@H]12- InChIKey
BVRDNJZFYKHRJQ-CWFCOSEVSA-N- Molecular formula
- C15H22O3
- Average molar mass
- 250.33 g/mol
- Monoisotopic mass
- 250.15689456
Overview
Arbusculin A is a sesquiterpene lactone isolated from Saussureae Radix and has been shown to exhibit inhibitory activity against melanogenesis. It has a role as a metabolite and a melanin synthesis inhibitor. It is a tertiary alcohol, an organic heterotricyclic compound and a sesquiterpene lactone.
Names & identifiers
- Preferred name
- (3aS,5aR,9R,9aS,9bS)-Decahydro-9-hydroxy-5a,9-dimethyl-3-methylenenaphtho(1,2-b)furan-2(3H)-one
- IUPAC
- (3aS,5aR,9R,9aS,9bS)-9-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
- English name
- arbusculin A
- Molecular formula
- C15H22O3
- Molecular weight
- 250.33
Names & synonyms
Arbusculin A27652-22-85ML8H8S9IS(3as,5ar,9r,9as,9bs)-9-hydroxy-5a,9-dimethyl-3-methylidenedecahydronaphtho[1,2-b]furan-2(3h)-oneCHEBI:2805(3aS,5aR,9R,9aS,9bS)-9-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-oneNaphtho(1,2-b)furan-2(3H)-one, decahydro-9-hydroxy-5a,9-dimethyl-3-methylene-, (3aS-(3aalpha,5abeta,9alpha,9aalpha,9bbeta))-(3aS,5aR,9R,9aS,9bS)-9-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo(g)(1)benzofuran-2-one(3aS,5aR,9R,9aS,9bS)-9-hydroxy-5a,9-dimethyl-3-methylidenedecahydronaphtho(1,2-b)furan-2(3H)-oneRefChem:905969(3aS,5aR,9R,9aS,9bS)-Decahydro-9-hydroxy-5a,9-dimethyl-3-methylenenaphtho(1,2-b)furan-2(3H)-one4-epiarbusculin A
Show more names
ARBUSCULINNaphtho[1,2-b]furan-2(3H)-one, decahydro-9-hydroxy-5a,9-dimethyl-3-methylene-, (3aS,5aR,9R,9aS,9bS)-(3aS)-9β-Hydroxy-3-methylene-5aα,9-dimethyl-3aβ,4,5,5a,6,7,8,9,9aβ,9bα-decahydronaphtho[1,2-b]furan-2(3H)-one(3aS,9aβ,9bα)-3aβ,4,5,5a,6,7,8,9,9a,9b-Decahydro-9β-hydroxy-5aα,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2(3H)-one
UNII-5ML8H8S9ISARBUSCULIN-A(+)-ARBUSCULIN ACHEMBL446602DTXSID50950304C09295Q271058234.ALPHA.H-EUDESM-11(13)-EN-12-OIC ACID, 4,6.ALPHA.-DIHYDROXY-, .GAMMA.-LACTONE
Database identifiers
- CAS
27652-22-8- PubChem CID
- 160153
- DTXSID
DTXSID50950304- ChEMBL
CHEMBL446602- ChEBI
CHEBI:2805- UNII
- 5ML8H8S9IS
- Nikkaji
- J20.240A
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 416
Physicochemical properties
- FDA UNII
- 5 ML8H8S9IS · 5ML8H8S9IS
Chemistry & industry
Additional notes
DefinitionChEBI: A sesquiterpene lactone isolated from Saussureae Radix and has been shown to exhibit inhibitory activity against melanogenesis.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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