Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside (CHEM031487)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:41:18 UTC
Update Date2016-11-09 01:19:16 UTC
Accession NumberCHEM031487
Identification
Common NamePeonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside
ClassSmall Molecule
DescriptionConstituent of fruits of Capsicum annuum. Capsianoside II is found in many foods, some of which are italian sweet red pepper, pepper (c. annuum), herbs and spices, and green bell pepper.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Capsianside IIHMDB
3,4',5,7-Tetrahydroxy-3'-methoxyflavylium(1+)HMDB
3-O-[4-Hydroxycinnamoyl-(->6)-b-D-glucopyranoside], 5-O-b-D-glucopyranosideHMDB
Peonidin 3-(6''-P-coumarylglucoside)-5-glucosideHMDB
Chemical FormulaC38H41O17
Average Molecular Mass769.722 g/mol
Monoisotopic Mass769.234 g/mol
CAS Registry Number51939-65-2
IUPAC Name5-{[(2S,4R,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-methyloxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
Traditional Name5-{[(2S,4R,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-methyloxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
SMILESCOC1=C(O)C=CC(=C1)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O)C(O[C@@H]1OC(CO)[C@@H](O)[C@H](O)C1C)=CC(O)=C2
InChI IdentifierInChI=1S/C38H40O17/c1-17-31(44)32(45)28(15-39)54-37(17)52-25-13-21(41)12-24-22(25)14-27(36(51-24)19-6-9-23(42)26(11-19)49-2)53-38-35(48)34(47)33(46)29(55-38)16-50-30(43)10-5-18-3-7-20(40)8-4-18/h3-14,17,28-29,31-35,37-39,44-48H,15-16H2,1-2H3,(H2-,40,41,42,43)/p+1/t17?,28?,29-,31-,32-,33-,34+,35-,37-,38-/m1/s1
InChI KeyUYFNRLODXGXIBD-VEMHFVEPSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentDiterpene glycosides
Alternative Parents
Substituents
  • Diterpene glycoside
  • Oligosaccharide
  • Diterpenoid
  • Fatty acyl glycoside
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty acyl
  • Oxane
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.071 g/LALOGPS
logP2.77ALOGPS
logP2.49ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)6.66ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area267.66 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity197.55 m³·mol⁻¹ChemAxon
Polarizability76.99 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_9) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0100000900-d6b8f85ed96ef6451c9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-1200000900-5e3797d874b3616e3214Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03du-7900000300-fc49e15b8ea9112d682dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0100000900-4e4d3f5cdcf8e2851cd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9100000200-d3588396098a799f6f4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9100001000-e629a85bb74b8cc72df0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0500901500-d10548f9cdaf11384321Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-0402903400-65b90ce62285af605cd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0910112100-69e30e3a53de979fdebcSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031892
FooDB IDFDB008577
Phenol Explorer IDNot Available
KNApSAcK IDC00029907
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131751202
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM