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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 04:09:20 UTC
Update Date2021-09-23 04:09:21 UTC
HMDB IDHMDB0301980
Secondary Accession NumbersNone
Metabolite Identification
Common NameVitexin 6''-O-malonyl 2''-O-xyloside
DescriptionVitexin, also known as apigenin 8-C-glucoside or 8-glycosylapigenin, belongs to the class of organic compounds known as flavonoid 8-C-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vitexin is also described as an apigenin flavone glucoside. Vitexin has been found in passion flower, chasteberry, bamboo leaves, millet and Hawthorn. Vitexin has shown a wide range of pharmacological effects, such as antioxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects (PMID: 27693342 ). Vitexin has also been shown to directly inhibit thyroid peroxidase and potentially contributes to goiter (PMID: 1696490 ). It is sometimes called a goitrogen.
Structure
Thumb
Synonyms
Chemical FormulaC21H20O10
Average Molecular Weight432.3775
Monoisotopic Molecular Weight432.10564686
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
Traditional Namevitexin
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1
InChI KeySGEWCQFRYRRZDC-VPRICQMDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • C-glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Monosaccharide
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001706
KNApSAcK IDC00001110
Chemspider ID4444098
KEGG Compound IDC01460
BioCyc IDVITEXIN
BiGG IDNot Available
Wikipedia LinkVitexin
METLIN IDNot Available
PubChem Compound5280441
PDB IDNot Available
ChEBI ID16954
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1667761
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. He M, Min JW, Kong WL, He XH, Li JX, Peng BW: A review on the pharmacological effects of vitexin and isovitexin. Fitoterapia. 2016 Dec;115:74-85. doi: 10.1016/j.fitote.2016.09.011. Epub 2016 Sep 28. [PubMed:27693342 ]
  2. Gaitan E: Goitrogens in food and water. Annu Rev Nutr. 1990;10:21-39. doi: 10.1146/annurev.nu.10.070190.000321. [PubMed:1696490 ]