Licorisoflavan A
Basic information
- CAS
129314-37-0- Standard SMILES
COc1cc2c(c(OC)c1CC=C(C)C)C[C@H](c1ccc(O)c(CC=C(C)C)c1O)CO2- InChIKey
GDAAEAXMNLVRCZ-SFHVURJKSA-N- Molecular formula
- C27H34O5
- Average molar mass
- 438.6 g/mol
- Monoisotopic mass
- 438.24062418
Overview
Licorisoflavan A is a member of the class of hydroxyisoflavans that is the 7-O-methyl derivative of licoricidin. Isolated from Glycyrrhiza uralensis, it exhibits antibacterial activity. It has a role as an antibacterial agent and a plant metabolite. It is an aromatic ether, a member of hydroxyisoflavans and a methoxyisoflavan. It is functionally related to a licoricidin.
Names & identifiers
- Preferred name
- Licorisoflavan A
- IUPAC
- 4-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]-2-(3-methylbut-2-enyl)benzene-1,3-diol
- English name
- 5-O-methyllicoricidin
- Molecular formula
- C27H34O5
- Molecular weight
- 438.56
Names & synonyms
Licorisoflavan A129314-37-0JW8U2YD8JLCHEBI:69083RefChem:408954-(5,7-dimethoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl)-2-(3-methylbut-2-enyl)benzene-1,3-diol(+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan5-O-MethyllicoricidinLicoriisoflavan A7-O-Methyllicoricidin4-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]-2-(3-methylbut-2-enyl)benzene-1,3-diol7-O-METHYLLICORISOFLAVAN B
Show more names
1,3-Benzenediol, 4-[(3R)-3,4-dihydro-5,7-dimethoxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-3-yl]-2-(3-methyl-2-buten-1-yl)-
LicorisoflavanA7-methyllicoricidin(+)-7-O-METHYLLICORICIDINUNII-JW8U2YD8JLorb1682211CHEMBL4635007SCHEMBL26115163SCHEMBL30631316
Database identifiers
- CAS
129314-37-0
Properties
Computed structural properties
- XLogP
- 6.8
- Topological polar surface area
- 68.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 7
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 650
Physicochemical properties
- Boiling point
- 589.2 · 589.2±50.0 °C(Predicted)
- Density
- 1.13 · 1.130±0.06 g/cm3(Predicted)
- pka
- 10.15 · 10.15±0.45(Predicted)
- FDA UNII
- 8 U2YD8JL · JW8U2YD8JL
Chemistry & industry
Applications
UsesLicorisoflavan A (7-O-Methyllicorisoflavan B) is a isoflavan-quinone, that can be isolated from Glycyrrhiza uralensis[1].
Additional notes
DefinitionChEBI: A member of the class of hydroxyisoflavans that is the 7-O-methyl derivative of licoricidin. Isolated from Glycyrrhiza uralensis, it exhibits antibacterial activity.
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