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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-13 00:02:11 UTC
Update Date2019-02-12 12:35:02 UTC
HMDB IDHMDB0125127
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium
Description2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium. It is generated by EC.3.2.1.X enzyme via a glycoside-hydrolysis reaction. This glycoside-hydrolysis occurs in human gut microbiota.
Structure
Data?1549974902
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-1-benzopyrylium chlorideHMDB
3,3',4',5,7-Pentahydroxy-2-phenylbenzopyrylium chlorideHMDB
3,3',4',5,7-Pentahydroxyflavylium chlorideHMDB
Cyanidin chlorideHMDB
CyanidineHMDB
CyanidolHMDB
Cyanidol chlorideHMDB
IdB 1027HMDB
Chemical FormulaC15H11O6
Average Molecular Weight287.2442
Monoisotopic Molecular Weight287.055563084
IUPAC Name2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium chloride
Traditional Namecyanidin chloride
CAS Registry NumberNot Available
SMILES
OC1=CC2=[O+]C(=C(O)C=C2C(O)=C1)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C15H10O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-6H,(H4-,16,17,18,19,20)/p+1
InChI KeyVEVZSMAEJFVWIL-UHFFFAOYSA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassHydroxyflavonoids
Direct Parent7-hydroxyflavonoids
Alternative Parents
Substituents
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Anthocyanidin
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic zwitterion
  • Organic salt
  • Organic chloride salt
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.41ALOGPS
logP3.05ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)6.01ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area114.29 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity84.11 m³·mol⁻¹ChemAxon
Polarizability28.11 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-0981000000-b03145f35dffd7b73034JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-001i-2062095000-78127582ff2f81e09993JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-f9880830ba79067d96b6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-f9880830ba79067d96b6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0009000000-f9880830ba79067d96b6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-eee166fbbcec693fd35dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0009000000-eee166fbbcec693fd35dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0009000000-eee166fbbcec693fd35dJSpectraViewer | MoNA
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
FoodDB IDFDB002602
KNApSAcK IDC00006614
Chemspider ID61546
KEGG Compound IDC05905
BioCyc IDCPD-7632
BiGG IDNot Available
Wikipedia LinkCyanidin
METLIN ID3413
PubChem Compound68247
PDB IDNot Available
ChEBI ID604446
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium → 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1λ⁴-chromen-1-yliumdetails
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
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium → 3-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-yliumdetails
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium → 2-{4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3-hydroxyphenyl}-3,5,7-trihydroxy-1λ⁴-chromen-1-yliumdetails
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium → 2-{3-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-4-hydroxyphenyl}-3,5,7-trihydroxy-1λ⁴-chromen-1-yliumdetails
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium → 5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-1λ⁴-chromen-1-yliumdetails
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium → (6-carboxy-3,4,5-trihydroxyoxan-2-yl)[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7H-chromen-7-ylidene]oxidaniumdetails