Glycyrin
Basic information
- CAS
66056-18-6- Standard SMILES
COc1cc2oc(=O)c(-c3ccc(O)cc3O)cc2c(OC)c1CC=C(C)C- InChIKey
FWWGXZYUURXJLK-UHFFFAOYSA-N- Molecular formula
- C22H22O6
- Average molar mass
- 382.4 g/mol
- Monoisotopic mass
- 382.14163842
Overview
Glycyrin is a member of the class of coumarins that is coumarin substituted by methoxy groups at positions 5 and 7, a prenyl group at position 6 and a 2,4-dihydroxyphenyl group at position 3. Isolated from Glycyrrhiza uralensis, it exhibits antibacterial activity. It has a role as a metabolite, an antibacterial agent and a plant metabolite. It is a member of coumarins, an aromatic ether and a member of hydroxyisoflavans.
Names & identifiers
- Preferred name
- Glycyrin
- IUPAC
- 3-(2,4-dihydroxyphenyl)-5,7-dimethoxy-6-(3-methylbut-2-enyl)chromen-2-one
- English name
- Glucyrin
- Molecular formula
- C22H22O6
- Molecular weight
- 382.41
Names & synonyms
Glycyrin66056-18-63-(2,4-dihydroxyphenyl)-5,7-dimethoxy-6-(3-methylbut-2-enyl)chromen-2-one3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-prenylcoumarin994BQ9M3AVCHEBI:69086RefChem:37944Glucyrin3-(2,4-Dihydroxy-phenyl)-5,7-dimethoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-2-oneUNII-994BQ9M3AV3-(2,4-dihydroxyphenyl)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-2h-chromen-2-oneCHEMBL132535
Show more names
3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one3-(2,4-Dihydroxyphenyl)-5,7-dimethoxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-2-one2H-1-Benzopyran-2-one, 3-(2,4-dihydroxyphenyl)-5,7-dimethoxy-6-(3-methyl-2-buten-1-yl)-3-(2,4-Dihydroxyphenyl)-5-methoxy-6-(3-methyl-2-butenyl)-7-methoxy-2H-1-benzopyran-2-one
orb1684565SCHEMBL5327472SCHEMBL29388094DTXSID50216255HY-N3960RCA05618LMPK12160017TN1703
Properties
Computed structural properties
- XLogP
- 4.7
- Topological polar surface area
- 85.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 5
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 623
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Other Flavonoids [PK1216]
Melting Point209 - 211 °C
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 614.1 · 614.1±55.0 °C(Predicted)
- Density
- 1.275 · 1.275±0.06 g/cm3(Predicted)
- pka
- 8.89 · 8.89±0.40(Predicted)
- FDA UNII
- 994 BQ9M3AV · 994BQ9M3AV
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
UsesGlycyrin can be used to treat COVID-19 based on network pharmacology and molecular docking. It can also be used to explore multi-component synergy mechanism of Banxia Xiexin, a prescription used to regulate spleen and stomach, decoction on Irritable Bowel Syndrome.
Additional notes
DefinitionChEBI: A member of the class of coumarins that is coumarin substituted by methoxy groups at positions 5 and 7, a prenyl group at position 6 and a 2,4-dihydroxyphenyl group at position 3. Isolated from Glycyrrhiza uralensis, it exhibits antibacterial ctivity.
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