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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:45 UTC
Update Date2020-07-07 18:02:59 UTC
HMDB IDHMDB0003263
Secondary Accession Numbers
  • HMDB0125089
  • HMDB03263
Metabolite Identification
Common NamePelargonidin
DescriptionPelargonidin, also known as pelargonidin chloride (CAS: 134-04-3) is an anthocyanin. Anthocyanins are water-soluble glycosides and acylglycosides of anthocyanidins, which are polyhydroxy and polymethoxyl derivatives of a 2-phenylbenzopyrylium (flavylium) cation. They are widely distributed in foods of plant origin, especially in fruits and vegetables with dark red and blue colours. Numerous epidemiologic and clinical trials show that fruits and vegetables, many of which are rich in anthocyanins, may be related to the decreased incidence of many chronic and degenerative diseases, including heart disease, cancer, and aging. Antioxidant mechanisms were suggested as potential means of disease prevention. Anthocyanins are strong antioxidants in vitro. In most cases, fruits and vegetables with high anthocyanin content were shown to have higher antioxidant capacity than other fruits and vegetables. Whether anthocyanins are effective antioxidants in vivo remains an open question primarily because of the relatively low apparent absorption of anthocyanins compared with other phenolic compounds (PMID: 15465754 ). BioTransformer predicts that pelargonidin is a product of 5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-3,7-dihydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium metabolism via a glycoside-hydrolysis reaction occurring in human gut microbiota and catalyzed by an EC.3.2.1.X enzyme (PMID: 30612223 ).
Structure
Data?1594144979
Synonyms
ValueSource
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1-benzopyryliumChEBI
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)benzopyrylium chlorideKegg
3,4',5,7-Tetrahydroxyflavylium chlorideKegg
Pelargonidin chlorideKegg
Pelargonidol chlorideKegg
PelargonidineMeSH
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chlorideMeSH
PelargonidinHMDB
PelarogonidinHMDB
Chemical FormulaC15H11O5
Average Molecular Weight271.2448
Monoisotopic Molecular Weight271.060648462
IUPAC Name3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2H-chromen-2-ylium
Traditional Name3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2H-chromen-2-ylium
CAS Registry Number7690-51-9
SMILES
OC1=CC=C(C=C1)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O
InChI Identifier
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-7H,(H3-,16,17,18,19)/p+1
InChI KeyXVFMGWDSJLBXDZ-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
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • 1-benzopyran
  • Benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • 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 Point> 350 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
logP2.94ALOGPS
logP-0.5ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)6.51ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area94.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.18 m³·mol⁻¹ChemAxon
Polarizability27.16 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-0590000000-433152a67ceebfb4760dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ( TMS) - 70eV, Positivesplash10-0076-3311940000-27f659d1235c6ca0641aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-05c26eb7b1cc94c37edfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-524aa4c208e3983d03d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j6r-1950000000-41c9c82ef0314d300395Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-1d1e62d6b2ab0749d0a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-e4330de55139f36af845Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005c-5950000000-ff425361fabac33a2ed4Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
    details
    UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 18 details
    UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 18 details
    UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 18 details
    UrineDetected and Quantified0.002 +/- 0.003 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
    UrineDetected and Quantified0.0005 +/- 0.0009 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 ID18
    FooDB IDFDB012426
    KNApSAcK IDC00007232
    Chemspider ID389676
    KEGG Compound IDC05904
    BioCyc IDPELARGONIDIN-CMPD
    BiGG IDNot Available
    Wikipedia LinkPelargonidin
    METLIN IDNot Available
    PubChem Compound440832
    PDB IDNot Available
    ChEBI ID25863
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceWillstatter, R.; Zechmeister, L. Syntheses of pelargonidin. Sitzb. kgl. preuss. Akad. (1914), 886-93. CAN 9:5222 AN 1915:5222
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Felgines C, Talavera S, Gonthier MP, Texier O, Scalbert A, Lamaison JL, Remesy C: Strawberry anthocyanins are recovered in urine as glucuro- and sulfoconjugates in humans. J Nutr. 2003 May;133(5):1296-301. [PubMed:12730413 ]
    2. Wu X, Pittman HE 3rd, Prior RL: Pelargonidin is absorbed and metabolized differently than cyanidin after marionberry consumption in pigs. J Nutr. 2004 Oct;134(10):2603-10. [PubMed:15465754 ]
    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 ]
    4. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

    Enzymes

    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
    Pelargonidin → (6-carboxy-3,4,5-trihydroxyoxan-2-yl)[4-(3,5,7-trihydroxy-2H-chromen-2-ylidene)cyclohexa-2,5-dien-1-ylidene]oxidaniumdetails
    Pelargonidin → 3-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-yliumdetails
    Pelargonidin → 7-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,5-dihydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-yliumdetails
    Pelargonidin → 5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,7-dihydroxy-2-(4-hydroxyphenyl)-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
    Pelargonidin → [dihydroxy(oxo)-λ⁶-sulfanylidene][4-(3,7-dihydroxy-5-oxo-5H-chromen-2-yl)phenyl]oxidaniumdetails