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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:33 UTC
Update Date2022-03-07 02:52:39 UTC
HMDB IDHMDB0030708
Secondary Accession Numbers
  • HMDB30708
Metabolite Identification
Common NameVicenin 2
DescriptionVicenin 2, also known as vicenin II, 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. Vicenin 2 is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Vicenin 2 has also been detected, but not quantified in, several different foods, such as barleys (Hordeum vulgare), sweet basils (Ocimum basilicum), bulgur, quinoas (Chenopodium quinoa), and red rice (Oryza rufipogon). This could make vicenin 2 a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Vicenin 2.
Structure
Data?1563862025
Synonyms
ValueSource
Apigenin-6,8-di-C-glycopyranosideMeSH
Vicenin-2MeSH
Vicenin IIMeSH
5,7,4'-Trihydroxyflavone-6,8-di-C-glucosideHMDB
6,8-Di-b-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9ciHMDB
6,8-Di-C-glucopyranosylapigeninHMDB
6,8-Di-C-glucosyl-4',5,7-trihydroxyflavoneHMDB
6,8-Di-C-glucosylapigeninHMDB
Apigenin 6,8-di-C-glucosideHMDB
Vicenin-1MeSH
6-C-beta-D-Xylopyranosyl-8-C-beta-D-glucopyranosyl apigeninMeSH
ViceninMeSH
Chemical FormulaC27H30O15
Average Molecular Weight594.5181
Monoisotopic Molecular Weight594.15847029
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
Traditional Name5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
CAS Registry Number23666-13-9
SMILES
OCC1OC(C(O)C(O)C1O)C1=C(O)C(C2OC(CO)C(O)C(O)C2O)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2
InChI KeyFIAAVMJLAGNUKW-UHFFFAOYSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point233 - 236 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility605600 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB002630
KNApSAcK IDC00006229
Chemspider ID2341472
KEGG Compound IDC10195
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3084407
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1822101
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Vicenin 2 → ({6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)sulfonic aciddetails
Vicenin 2 → ({6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-6-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)sulfonic aciddetails
Vicenin 2 → {2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
Vicenin 2 → {2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-8-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxidanesulfonic aciddetails
Vicenin 2 → {6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-8-yl]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
Vicenin 2 → {6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-6-yl]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
Vicenin 2 → {2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-6-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxidanesulfonic aciddetails
Vicenin 2 → {2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Vicenin 2 → 6-(4-{5,7-dihydroxy-4-oxo-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-2-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Vicenin 2 → 3,4,5-trihydroxy-6-{[7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-5-yl]oxy}oxane-2-carboxylic aciddetails
Vicenin 2 → 3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-7-yl]oxy}oxane-2-carboxylic aciddetails