Showing Compound Card for Vitexin (CDB000738)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:54:08 UTC
Updated at2020-12-07 19:07:44 UTC
CannabisDB IDCDB000738
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameVitexin
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 is an active component in many traditional Chinese medicines and it is also one of 23 flavonoids that have been identified in cannabis plants (PMID: 6991645 ). It has also 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
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Apigenin 8-C-glucosideChEBI
8-Glycosyl-apigeninMeSH
8-GlycosylapigeninMeSH
8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-onePhytoBank
8-β-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-onePhytoBank
5,7,4'-Trihydroxyflavone 8-C-beta-D-glucopyranosidePhytoBank
5,7,4'-Trihydroxyflavone 8-C-β-D-glucopyranosidePhytoBank
5,7,4’-Trihydroxyflavone 8-C-β-D-glucopyranosidePhytoBank
8-C-GlucosylapigeninPhytoBank
8-C-beta-D-GlucopyranosylapigeninPhytoBank
8-C-β-D-GlucopyranosylapigeninPhytoBank
Apigenin 8-C-beta-D-glucosidePhytoBank
Apigenin 8-C-β-D-glucosidePhytoBank
Apigenin 8-C-beta-glucopyranosidePhytoBank
Apigenin 8-C-β-glucopyranosidePhytoBank
Apigenin-8-C-beta-D-glucopyranosidePhytoBank
Apigenin-8-C-β-D-glucopyranosidePhytoBank
OrientosidePhytoBank
VitexinaPhytoBank
VitexinePhytoBank
Chemical FormulaC21H20O10
Average Molecular Weight432.38
Monoisotopic Molecular Weight432.1056
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 Number521-33-5
SMILES
OC[C@H]1OC([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)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
Role

Indirect biological role:

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point203 to 204 °CWikipedia
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.36ALOGPS
logP-0.051ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.17ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity106.03 m³·mol⁻¹ChemAxon
Polarizability41.52 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-00lr-0980000000-a7106606775ccbb5f8772017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 70V, Negativesplash10-014i-0920000000-ff12e5d6160ba32672092017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0920000000-ff12e5d6160ba32672092017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0920000000-ff12e5d6160ba32672092017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-01q9-0096000000-5352d14a270cef7d05732017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-001i-0190000000-33aab7c5c534e3bd93d22017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, positivesplash10-001i-0189600000-fd0b1e9721d23e12d4c62020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-001i-0048900000-f581534a320bf875bc5f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-02ai-0029400000-1abc6ec4a624fc7ffdbf2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-03yj-0019400000-f245a00fa402ce62fbeb2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-001i-0047900000-74b4b570ebb03db5e2d42020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-03e9-0049000000-d0c10f5af6fd40c34bbf2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-053r-0490000000-4f55f96dd316c01bf6b42020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-015a-0019700000-0c79eae7767fc558a3182020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-03yj-0029200000-b9b5015bff3ee345cfae2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-03e9-0049000000-c5394c9b574d285346682020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-01q9-0098000000-6af859afe0807d2c57382020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-01q9-0095000000-70a6a6fd27047ca2c6662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 30V, positivesplash10-014i-0009700000-98479ff8e0b88ae1ab792020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0001900000-958c99e5dd8f93cb7d842016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-4324900000-09b1bdaa3f1336b36f0a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-5194000000-bca39f308b9ddf54a00b2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1011900000-a6689e1e349d5b719f2d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-045c-9256700000-24a4b43d1cb46da46b7d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mp-9262000000-72d91a652228e0bd5d482016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Thyroid peroxidaseTPO2p25P07202 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Thyroid peroxidaseTPO2p25P07202 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0301980
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. 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 ]
  3. Gaitan E: Goitrogens in food and water. Annu Rev Nutr. 1990;10:21-39. doi: 10.1146/annurev.nu.10.070190.000321. [PubMed:1696490 ]

Enzymes

Enzyme Details
1. Thyroid peroxidase
General function:
Involved in calcium ion binding
Specific function:
Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name:
TPO
Uniprot ID:
P07202
Molecular weight:
102961.63