Record Information
Version1.0
Creation date2010-04-08 22:09:49 UTC
Update date2019-11-26 03:05:24 UTC
Primary IDFDB011782
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePelargonidin 3-sophoroside
DescriptionPelargonidin 3-sophoroside belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. Pelargonidin 3-sophoroside is found, on average, in the highest concentration within red raspberries (Rubus idaeus). Pelargonidin 3-sophoroside has also been detected, but not quantified in, scarlet beans (Phaseolus coccineus). This could make pelargonidin 3-sophoroside a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Pelargonidin 3-sophoroside.
CAS Number54542-60-8
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.6 g/LALOGPS
logP0.7ALOGPS
logP-0.12ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.4ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area232.13 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity149.8 m³·mol⁻¹ChemAxon
Polarizability58.59 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H33O14
IUPAC name3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C28H32O14/c1-11-21(34)22(35)19(9-29)40-27(11)42-26-24(37)23(36)20(10-30)41-28(26)39-18-8-15-16(33)6-14(32)7-17(15)38-25(18)12-2-4-13(31)5-3-12/h2-8,11,19-24,26-30,34-37H,9-10H2,1H3,(H2-,31,32,33)/p+1/t11-,19-,20-,21-,22-,23-,24+,26-,27+,28-/m1/s1
InChI KeyMJCMQFQZXCYZOU-ZKUUPHCGSA-O
Isomeric SMILESC[C@H]1[C@H](O[C@H]2[C@H](OC3=CC4=C(C=C(O)C=C4O)[O+]=C3C3=CC=C(O)C=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O
Average Molecular Weight593.5532
Monoisotopic Molecular Weight593.187030764
Classification
Description Belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin-3-O-glycosides
Alternative Parents
Substituents
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPelargonidin 3-sophoroside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01si-7110190000-f250106d93f6878443e8Spectrum
Predicted GC-MSPelargonidin 3-sophoroside, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-8110019000-93c0a5bd8d08d3de3941Spectrum
Predicted GC-MSPelargonidin 3-sophoroside, "Pelargonidin 3-sophoroside,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPelargonidin 3-sophoroside, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0300090000-0fc3f97a77536bb93d902016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-1301090000-da7df3c68445b2b4db1d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p6-6911010000-b334901fe3d82704f79b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1512090000-c1476741c3185c56e3af2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9500010000-3d57f7e1924c7f52a6702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-5900000000-f9910051071fce96ae0a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0000090000-f8ac9ff0efba151dca132021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0310190000-f7422cf14ac81b7402182021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvl-5691200000-a64659fd0c6a9959de292021-09-23View Spectrum
NMRNot Available
ChemSpider ID30777026
ChEMBL IDNot Available
KEGG Compound IDC16305
Pubchem Compound ID23724704
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID22
DrugBank IDNot Available
HMDB IDHMDB33679
CRC / DFC (Dictionary of Food Compounds) IDHGV59-L:GZF66-B
EAFUS IDNot Available
Dr. Duke IDPELARGONIDIN-3-SOPHOROSIDE
BIGG IDNot Available
KNApSAcK IDC00006636
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID22
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.