| Common Name |
Liquiritin
| Description |
Liquiritin is found in herbs and spices. Liquiritin is isolated from Glycyrrhiza glabra (licorice) and Glycyrrhiza uralensis (Chinese licorice) Liquiritin has been shown to exhibit anti-depressant function (PMID 18289754 ).Liquiritin belongs to the family of Flavonoid O-Glycosides. These are compounds containing a carbohydrate moiety which is o-glycosidically linked to one of the flavonoid backbones (2-phenylchromen-4-one, 3-phenylchromen-4-one or 4-phenylcoumarin).
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29520 (Liquiritin)
| Synonyms |
| Value |
Source |
4',7-Dihydroxyflavanone 4'-(beta-D-glucopyranoside)HMDB
4',7-Dihydroxyflavanone 4'-(beta-D-glucoside)HMDB
7-Hydroxyflavanone 4'-O-glucosideHMDB
LikviritinHMDB
LiquiritosideHMDB
| Chemical Formlia |
C21H22O9
| Average Molecliar Weight |
418.394
| Monoisotopic Molecliar Weight |
418.126382302
| IUPAC Name |
7-hydroxy-2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2H-1-benzopyran-4-one
| Traditional Name |
7-hydroxy-2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzopyran-4-one
| CAS Registry Number |
551-15-5
| SMILES |
OCC1OC(OC2=CC=C(C=C2)C2CC(=O)C3=C(O2)C=C(O)C=C3)C(O)C(O)C1O
| InChI Identifier |
InChI=1S/C21H22O9/c22-9-17-18(25)19(26)20(27)21(30-17)28-12-4-1-10(2-5-12)15-8-14(24)13-6-3-11(23)7-16(13)29-15/h1-7,15,17-23,25-27H,8-9H2
| InChI Key |
DEMKZLAVQYISIA-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as flavonoid o-glycosides. These are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Phenylpropanoids and polyketides
| Sub Class |
Flavonoids
| Direct Parent |
Flavonoid O-glycosides
| Alternative Parents |
7-hydroxyflavonoids
Flavanones
Phenolic glycosides
Hexoses
Chromones
O-glycosyl compounds
Aryl alkyl ketones
Phenoxy compounds
Phenol ethers
1-hydroxy-2-unsubstituted benzenoids
Alkyl aryl ethers
Oxanes
Secondary alcohols
Acetals
Polyols
Oxacyclic compounds
Hydrocarbon derivatives
Primary alcohols
Organic oxides
| Substituents |
Flavonoid-4p-o-glycoside
Flavonoid o-glycoside
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Phenoxy compound
Aryl alkyl ketone
Aryl ketone
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Secondary alcohol
Ketone
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
anti-depressant
| Application |
Nutrient
| Cellliar locations |
Cytoplasm
Extracellliar
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point212 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.98 mg/mLALOGPS
logP0.43ALOGPS
logP0.22ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.8ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.45 m3·mol-1ChemAxon
Polarizability41.93 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-066r-0070900000-46ea92a0b30441b59a05View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-0a4i-0190000000-870077f4ca693ab1b14dView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-00kr-0900000000-fd307cf29d74444caaf6View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0a4i-0090000000-76cae76d04d47f2d9425View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0a4i-0290000000-c96f557fc203dc65a1b3View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000656
| KNApSAcK ID |
C00008193
| Chemspider ID |
3021864
| KEGG Compound ID |
C16989
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29520
| Metagene Link |
HMDB29520
| METLIN ID |
Not Available
| PubChem Compound |
3794292
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: alpha-Hederin
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Wang W, Hu X, Zhao Z, Liu P, Hu Y, Zhou J, Zhou D, Wang Z, Guo D, Guo H: Antidepressant-like effects of liquiritin and isoliquiritin from Glycyrrhiza uralensis in the forced swimming test and tail suspension test in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2008 Jul 1;32(5):1179-84. doi: 10.1016/j.pnpbp.2007.12.021. Epub 2008 Jan 18. [PubMed:18289754 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 18757362
