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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:22:45 UTC
Update Date2022-03-07 02:55:37 UTC
HMDB IDHMDB0038095
Secondary Accession Numbers
  • HMDB38095
Metabolite Identification
Common NamePetanin
DescriptionPetanin belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. Based on a literature review a significant number of articles have been published on Petanin.
Structure
Data?1563863139
Synonyms
ValueSource
Petunidin 3-O-[6-O-(4-O-(e)-P-coumaroyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranosideHMDB
Chemical FormulaC43H49O23
Average Molecular Weight933.8354
Monoisotopic Molecular Weight933.266462874
IUPAC Name2-(3,4-dihydroxy-5-methoxyphenyl)-3-[(6-{[(3,4-dihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-6-methyloxan-2-yl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-7-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
Traditional Name2-(3,4-dihydroxy-5-methoxyphenyl)-3-[(6-{[(3,4-dihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-6-methyloxan-2-yl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-7-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
CAS Registry Number69915-09-9
SMILES
COC1=CC(=CC(O)=C1O)C1=C(OC2OC(COC3OC(C)C(OC(=O)\C=C\C4=CC=C(O)C=C4)C(O)C3O)C(O)C(O)C2O)C=C2C(OC3OC(CO)C(O)C(O)C3O)=CC(O)=CC2=[O+]1
InChI Identifier
InChI=1S/C43H48O23/c1-16-39(66-29(48)8-5-17-3-6-19(45)7-4-17)35(54)38(57)41(60-16)59-15-28-32(51)34(53)37(56)43(65-28)63-26-13-21-23(61-40(26)18-9-22(47)30(49)25(10-18)58-2)11-20(46)12-24(21)62-42-36(55)33(52)31(50)27(14-44)64-42/h3-13,16,27-28,31-39,41-44,50-57H,14-15H2,1-2H3,(H3-,45,46,47,48,49)/p+1
InChI KeyBXEZTCOKOLHMKY-UHFFFAOYSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin-5-O-glycosides
Alternative Parents
Substituents
  • Anthocyanidin-3-o-glycoside
  • Anthocyanidin-5-o-glycoside
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Coumaric acid ester
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Hydroxycinnamic acid or derivatives
  • Glycosyl compound
  • Disaccharide
  • O-glycosyl compound
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Catechol
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Styrene
  • Fatty acid ester
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Oxane
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Primary alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP1.58ALOGPS
logP-0.15ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.66ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area367.04 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity227.28 m³·mol⁻¹ChemAxon
Polarizability91.6 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+286.83230932474
DeepCCS[M-H]-284.93730932474
DeepCCS[M-2H]-318.84730932474
DeepCCS[M+Na]+292.86530932474
AllCCS[M+H]+278.832859911
AllCCS[M+H-H2O]+279.332859911
AllCCS[M+NH4]+278.332859911
AllCCS[M+Na]+278.232859911
AllCCS[M-H]-268.432859911
AllCCS[M+Na-2H]-273.732859911
AllCCS[M+HCOO]-279.532859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Petanin , positive-QTOFsplash10-014i-0009100101-f7ee26b8ed2dc09a731e2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petanin 10V, Positive-QTOFsplash10-001i-0100000009-0fbca2e34c4559ea57632016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petanin 20V, Positive-QTOFsplash10-006x-0200000009-b15590ccd5b0b85a1e162016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petanin 40V, Positive-QTOFsplash10-03dm-5900000103-24591fb1146076b706dc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petanin 10V, Negative-QTOFsplash10-001i-1100000009-4deb4f6bd88761add72f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petanin 20V, Negative-QTOFsplash10-001r-4500000009-783f3dd758dabf1bd7be2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petanin 40V, Negative-QTOFsplash10-0596-9100100000-9bc045bdc215ebad7c1a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petanin 10V, Positive-QTOFsplash10-00lr-0000101109-f2923b044ce9efdd50842021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petanin 20V, Positive-QTOFsplash10-00ec-0400309204-ada9d1952dd55e4493de2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petanin 40V, Positive-QTOFsplash10-02ta-0900201000-4c2d8216e77395612cf82021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FooDB IDNot Available
KNApSAcK IDC00006900
Chemspider ID24842409
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44256967
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .