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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:05 UTC
Update Date2022-03-07 02:49:16 UTC
HMDB IDHMDB0002708
Secondary Accession Numbers
  • HMDB0125127
  • HMDB02708
Metabolite Identification
Common NameCyanidin
DescriptionCyanidin, also known as cyanidin chloride (CAS: 528-58-5), 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. Thus, cyanidin is considered to be a flavonoid lipid molecule. Cyanidin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Cyanidin (and its glycosides) is the most commonly occurring of the anthocyanins, a widespread group of pigments responsible for the red-blue colour of many fruits and vegetables (PMID: 14711454 ). BioTransformer predicts that cyanidin is a product of cyanidin 3-​glucoside metabolism via a glycoside-hydrolysis reaction occurring in human gut microbiota and catalyzed by the EC.3.2.1.X enzyme (PMID: 30612223 ).
Structure
Data?1587575307
Synonyms
Chemical FormulaC15H11O6
Average Molecular Weight287.2442
Monoisotopic Molecular Weight287.055563084
IUPAC Name2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2H-chromen-2-ylium
Traditional Name2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2H-chromen-2-ylium
CAS Registry Number13306-05-3
SMILES
OC1=CC(O)=C2C=C(O)C(=[O+]C2=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
Description 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
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point> 300 °CNot 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 Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Fibroblasts
  • Kidney
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.02 (0.03 +/- 0.01) uMAdult (>18 years old)Not SpecifiedNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 19 details
UrineDetected and Quantified1.04 +/- 0.26 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002602
KNApSAcK IDC00006614
Chemspider ID114193
KEGG Compound IDC05905
BioCyc IDCPD-591
BiGG IDNot Available
Wikipedia LinkCyanidin
METLIN IDNot Available
PubChem Compound128861
PDB IDNot Available
ChEBI ID27843
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSaito, Norio; Yokoi, Masato; Yamaji, Minako; Honda, Toshio. Cyanidin 3-p-coumaroylglucoside in Camellia species and cultivars. Phytochemistry (1987), 26(10), 2761-2.
Material Safety Data Sheet (MSDS)Download (PDF)
General References

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
Cyanidin → 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
Cyanidin → 3-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-yliumdetails
Cyanidin → 2-{4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3-hydroxyphenyl}-3,5,7-trihydroxy-1λ⁴-chromen-1-yliumdetails
Cyanidin → 2-{3-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-4-hydroxyphenyl}-3,5,7-trihydroxy-1λ⁴-chromen-1-yliumdetails
Cyanidin → 5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-1λ⁴-chromen-1-yliumdetails
Cyanidin → (6-carboxy-3,4,5-trihydroxyoxan-2-yl)[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7H-chromen-7-ylidene]oxidaniumdetails