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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:38 UTC
Update Date2020-06-15 17:04:52 UTC
HMDB IDHMDB0003173
Secondary Accession Numbers
  • HMDB0131422
  • HMDB03173
Metabolite Identification
Common NamePetunidin
DescriptionPetunidin, also known as petunidin chloride (CAS: 1429-30-7), belongs to the class of organic compounds known as 3'-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone. Petunidin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, petunidin has been detected, but not quantified in, several different foods, such as saffrons, french plantains, highbush blueberries, bilberries, and fruits. This could make petunidin a potential biomarker for the consumption of these foods. Petunidin is an anthocyanin. Anthocyanins are water-soluble pigments belonging to the flavonoids compound family that are widespread in nature and involved in numerous functions such as flower, fruit, and seed pigmentation to attract pollinators, seed dispersion, UV light protection, and plant defence against pathogen attack. Because anthocyanins impart much of the colour and flavour of fruits and vegetables, they are usually components of the human diet and are not only considered exclusively as food products but also as therapeutic agents. In fact, anthocyanins have been suggested to protect against oxidative stress, coronary heart diseases, certain cancers, and other age-related diseases. At least part of these presumed health-promoting features can be attributed to the antioxidant properties of these compounds whose chemical structure appears ideal for free radical scavenging (PMID: 16277406 ). BioTransformer predicts that petunidin is a product of peonidin metabolism via a hydroxylation-of-benzene-ortho-to-edg reaction catalyzed by the CYP1A2, CYP2C9, and CYP3A4 enzymes (PMID: 30612223 ).
Structure
Data?1583427196
Synonyms
ValueSource
2-(3,4-Dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-1-benzopyryliumChEBI
3,3',4',5,7-Pentahydroxy-5'-methoxyflavyliumChEBI
Petunidin chlorideChEBI
PetunidolChEBI
PtChEBI
PetunidinHMDB
Chemical FormulaC16H13O7
Average Molecular Weight317.2702
Monoisotopic Molecular Weight317.06612777
IUPAC Name2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-1lambda4-chromen-1-ylium
Traditional Name2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-1lambda4-chromen-1-ylium
CAS Registry Number13270-60-5
SMILES
COC1=C(O)C(O)=CC(=C1)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O
InChI Identifier
InChI=1S/C16H12O7/c1-22-14-3-7(2-11(19)15(14)21)16-12(20)6-9-10(18)4-8(17)5-13(9)23-16/h2-6H,1H3,(H4-,17,18,19,20,21)/p+1
InChI KeyAFOLOMGWVXKIQL-UHFFFAOYSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent3'-O-methylated flavonoids
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Catechol
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Polyol
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP2.43ALOGPS
logP2.8ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)5.99ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area123.52 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity90.58 m³·mol⁻¹ChemAxon
Polarizability31.1 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-0973000000-4aa62cd463c1b445c1f3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ( TMS) - 70eV, Positivesplash10-03di-2003009000-1a401589995291a7fec4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-aac32478694d938b8f28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009000000-cf6d3f5291cb238a6700Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1933000000-8f14a609c74ddf705ba1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-41a90980eabff65cb37bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1019000000-13116a2ded16699a0a96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-6951000000-8d3c069b6b4741674d5eSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 ID30
FooDB IDFDB002755
KNApSAcK IDNot Available
Chemspider ID390371
KEGG Compound IDC08727
BioCyc IDCPD-15003
BiGG IDNot Available
Wikipedia LinkPetunidin
METLIN IDNot Available
PubChem Compound441774
PDB IDNot Available
ChEBI ID75318
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Garcia-Alonso M, Rimbach G, Sasai M, Nakahara M, Matsugo S, Uchida Y, Rivas-Gonzalo JC, De Pascual-Teresa S: Electron spin resonance spectroscopy studies on the free radical scavenging activity of wine anthocyanins and pyranoanthocyanins. Mol Nutr Food Res. 2005 Dec;49(12):1112-9. [PubMed:16254886 ]
  2. Lo Piero AR, Puglisi I, Rapisarda P, Petrone G: Anthocyanins accumulation and related gene expression in red orange fruit induced by low temperature storage. J Agric Food Chem. 2005 Nov 16;53(23):9083-8. [PubMed:16277406 ]
  3. Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]

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
Petunidin → 3,5,7-trihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-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
Petunidin → 3-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-yliumdetails
Petunidin → (6-carboxy-3,4,5-trihydroxyoxan-2-yl)[2-(3,4-dihydroxy-5-methoxyphenyl)-3,5-dihydroxy-7H-chromen-7-ylidene]oxidaniumdetails
Petunidin → 5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-(3,4-dihydroxy-5-methoxyphenyl)-3,7-dihydroxy-1λ⁴-chromen-1-yliumdetails
Petunidin → 2-{4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3-hydroxy-5-methoxyphenyl}-3,5,7-trihydroxy-1λ⁴-chromen-1-yliumdetails
Petunidin → 2-{3-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-4-hydroxy-5-methoxyphenyl}-3,5,7-trihydroxy-1λ⁴-chromen-1-yliumdetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Petunidin → {3-hydroxy-2-[3-hydroxy-5-methoxy-4-(sulfooxy)phenyl]-5-oxo-5H-chromen-7-yl}oxidaniumdetails