Lespeflorin A3
Basic information
- CAS
1108717-51-6- Standard SMILES
CC(C)=CCc1cc2c(c(CC=C(C)C)c1O)O[C@H](c1ccc3c(c1)C=CC(C)(C)O3)CC2=O- InChIKey
SAZBMMMZQLNWMN-MHZLTWQESA-N- Molecular formula
- C30H34O4
- Average molar mass
- 458.6 g/mol
- Monoisotopic mass
- 458.24570956
Overview
Lespeflorin A3 is a monohydroxyflavanone that is flavanone substituted with a hydroxy group at position 7, prenyl groups at positions 6 and 8 and a 6,6-dimethyl-3,6-dihydro-2H-pyran ring fused across positions 3' and 4'. Isolated from the roots of Lespedeza floribunda, it acts as a melanin synthesis inhibitor. It has a role as a metabolite and a melanin synthesis inhibitor.
Names & identifiers
- Preferred name
- Lespeflorin A3
- IUPAC
- (2S)-2-(2,2-dimethylchromen-6-yl)-7-hydroxy-6,8-bis(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Names & synonyms
Lespeflorin A3CHEBI:66560(2S)-7-hydroxy-2',2'-dimethyl-6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-2'H,4H-2,6'-bichromen-4-one(2S)-2-(2,2-dimethylchromen-6-yl)-7-hydroxy-6,8-bis(3-methylbut-2-enyl)-2,3-dihydrochromen-4-oneRefChem:1048369CHEMBL550552DTXSID4011170361108717-51-6Q27135172(2S)-7-Hydroxy-2',2'-dimethyl-6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-2'H,4H-[2,6'-bi-1-benzopyran]-4-one(2S)-7-Hydroxy-2a(2),2a(2)-dimethyl-6,8-bis(3-methyl-2-buten-1-yl)[2,6a(2)-bi-2H-1-benzopyran]-4(3H)-one
Database identifiers
- CAS
1108717-51-6- PubChem CID
- 25243166
- DTXSID
DTXSID401117036- ChEMBL
CHEMBL550552- ChEBI
CHEBI:66560- Nikkaji
- J2.699.697J
Properties
Computed structural properties
- XLogP
- 7.3
- Topological polar surface area
- 55.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 829
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