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Record Information
Version5.0
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 Molecular Properties
PropertyValueReference
Melting Point> 350 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available163.45831661259
DarkChem[M-H]-PredictedNot Available164.17831661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Pelargonidin,1TMS,#13014.5667https://arxiv.org/abs/1905.12712
Pelargonidin,1TMS,#23004.645https://arxiv.org/abs/1905.12712
Pelargonidin,1TMS,#32983.749https://arxiv.org/abs/1905.12712
Pelargonidin,1TMS,#42992.452https://arxiv.org/abs/1905.12712
Pelargonidin,2TMS,#12940.0342https://arxiv.org/abs/1905.12712
Pelargonidin,2TMS,#22945.2954https://arxiv.org/abs/1905.12712
Pelargonidin,2TMS,#33028.7844https://arxiv.org/abs/1905.12712
Pelargonidin,2TMS,#42974.8118https://arxiv.org/abs/1905.12712
Pelargonidin,2TMS,#53011.2417https://arxiv.org/abs/1905.12712
Pelargonidin,2TMS,#62997.301https://arxiv.org/abs/1905.12712
Pelargonidin,3TMS,#12864.3198https://arxiv.org/abs/1905.12712
Pelargonidin,3TMS,#22891.3137https://arxiv.org/abs/1905.12712
Pelargonidin,3TMS,#32890.5374https://arxiv.org/abs/1905.12712
Pelargonidin,3TMS,#42928.571https://arxiv.org/abs/1905.12712
Pelargonidin,4TMS,#12925.708https://arxiv.org/abs/1905.12712
Pelargonidin,1TBDMS,#13293.2983https://arxiv.org/abs/1905.12712
Pelargonidin,1TBDMS,#23279.6033https://arxiv.org/abs/1905.12712
Pelargonidin,1TBDMS,#33254.7476https://arxiv.org/abs/1905.12712
Pelargonidin,1TBDMS,#43289.3113https://arxiv.org/abs/1905.12712
Pelargonidin,2TBDMS,#13531.4688https://arxiv.org/abs/1905.12712
Pelargonidin,2TBDMS,#23539.8618https://arxiv.org/abs/1905.12712
Pelargonidin,2TBDMS,#33596.5916https://arxiv.org/abs/1905.12712
Pelargonidin,2TBDMS,#43548.1047https://arxiv.org/abs/1905.12712
Pelargonidin,2TBDMS,#53593.6904https://arxiv.org/abs/1905.12712
Pelargonidin,2TBDMS,#63587.1152https://arxiv.org/abs/1905.12712
Pelargonidin,3TBDMS,#13681.4128https://arxiv.org/abs/1905.12712
Pelargonidin,3TBDMS,#23716.8354https://arxiv.org/abs/1905.12712
Pelargonidin,3TBDMS,#33709.4688https://arxiv.org/abs/1905.12712
Pelargonidin,3TBDMS,#43709.0688https://arxiv.org/abs/1905.12712
Pelargonidin,4TBDMS,#13843.551https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-0590000000-433152a67ceebfb4760d2017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ( TMS) - 70eV, Positivesplash10-0076-3311940000-27f659d1235c6ca0641a2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - QTOF 6V, negativesplash10-014i-0090000000-ea3de9aeb3c6302fbfd62020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 8V, negativesplash10-014i-0190000000-e528f22236457f7bb1f92020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, negativesplash10-014i-0290000000-32ea61b58eda57ea7d492020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 12V, negativesplash10-014i-0490000000-a6727c20673446687f982020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, negativesplash10-014j-0790000000-56b7795234182d2265412020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 2V, negativesplash10-014i-0090000000-9e3ce437f443fde49fd92020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, negativesplash10-002f-0490000000-04d40c2efd76af71ca382020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-00xr-0190000000-c645c45f57c1bcfb43a42020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-00di-0090000000-68cd52d520111f5f4bd42020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 6V, positivesplash10-00di-0940000000-f04426014dc542ea58b42020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 8V, positivesplash10-00di-0930000000-3bdc8c841ce0c63326852020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-00di-0910000000-a635fef1540d29a4b7862020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 12V, positivesplash10-00di-0910000000-06fcbbe5e27cc9a2bf8a2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-00di-0900000000-ae6ce276f7d55aa3e29d2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 18V, positivesplash10-00di-0090000000-db8d9742becb27ed1c152020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-00di-0090000000-cf39a7e66f947a39bc782020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 22V, positivesplash10-00di-0090000000-e18063391fa2bcaffcd12020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-00di-0190000000-8f1ff0a9e88a790097c32020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-00di-0290000000-a33b9fec7b5573ee50c52020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-05c26eb7b1cc94c37edf2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-524aa4c208e3983d03d52017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j6r-1950000000-41c9c82ef0314d3003952017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-1d1e62d6b2ab0749d0a32017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-e4330de55139f36af8452017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005c-5950000000-ff425361fabac33a2ed42017-06-28View Spectrum
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
      Not Available
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
MarkerDB 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