Record Information
Version1.0
Creation date2010-04-08 22:12:52 UTC
Update date2020-09-17 15:41:09 UTC
Primary IDFDB017165
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3-sambubioside 5-glucoside
DescriptionCyanidin 3-sambubioside 5-glucoside, also known as cyanidin 5-glucoside 3-sambubioside, belongs to the class of organic compounds known as anthocyanidin-7-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C7-position. Cyanidin 3-sambubioside 5-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cyanidin 3-sambubioside 5-glucoside is found, on average, in the highest concentration within black elderberries. Cyanidin 3-sambubioside 5-glucoside has also been detected, but not quantified in, several different foods, such as common pea, gooseberries, redcurrants, black chokeberries, and blackcurrants. This could make cyanidin 3-sambubioside 5-glucoside a potential biomarker for the consumption of these foods.
CAS Number53925-33-0
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility3.17 g/LALOGPS
logP-0.56ALOGPS
logP-3.7ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.65ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area331.51 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity174.85 m³·mol⁻¹ChemAxon
Polarizability70.81 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC32H39O20
IUPAC name3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
InChI IdentifierInChI=1S/C32H38O20/c33-7-19-22(40)24(42)27(45)31(50-19)48-17-5-11(35)4-16-12(17)6-18(28(47-16)10-1-2-13(36)14(37)3-10)49-32-29(25(43)23(41)20(8-34)51-32)52-30-26(44)21(39)15(38)9-46-30/h1-6,15,19-27,29-34,38-45H,7-9H2,(H2-,35,36,37)/p+1
InChI KeyOLBLWNPOURNBCY-UHFFFAOYSA-O
Isomeric SMILESOCC1OC(OC2=C3C=C(OC4OC(CO)C(O)C(O)C4OC4OCC(O)C(O)C4O)C(=[O+]C3=CC(O)=C2)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O
Average Molecular Weight743.6401
Monoisotopic Molecular Weight743.203468688
Classification
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-5-o-glycoside
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • O-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • 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-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_1_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-sambubioside 5-glucoside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 6V, positivesplash10-000f-0070210900-169d83d42398b3dae64d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 6V, negativesplash10-0059-0040290200-dd2647ccf29b421e785c2020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0400000900-160c5c82baa93948681c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-0610000900-c941618c540b9904cdaa2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-5900001100-de89d3321edb9d8c2b012016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-2821000900-0e2ec84fa85144adf0b02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-2900000100-5dd52fe130f9d5bb1bbc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-6e57eddaf636a1e4e5fb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0000739300-d67a2b992240e84f4f8b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p5-0020596200-345c3d18f2da32009b032021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007k-2940860100-52def066532e8b27f7632021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID69
DrugBank IDNot Available
HMDB IDHMDB37980
CRC / DFC (Dictionary of Food Compounds) IDODW40-I:KWM78-M
EAFUS IDNot Available
Dr. Duke IDCYANIDIN-3-SAMBUBIOSIDE-5-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00006673
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 ID69
Duplicate IDSNot Available
Old DFC IDSCMQ73-Z:KWM78-M
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— 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.
— 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.