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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:25 UTC
Update Date2019-07-23 06:08:48 UTC
HMDB IDHMDB0031458
Secondary Accession Numbers
  • HMDB31458
Metabolite Identification
Common NameCyanidin 3-rutinoside
DescriptionCyanidin 3-rutinoside, also known as keracyanin or sambucin, belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). Cyanidin 3-rutinoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cyanidin 3-rutinoside is found, on average, in the highest concentration within a few different foods, such as sweet cherries, olives, and black elderberries and in a lower concentration in rubus (blackberry, raspberry), cloudberries, and gooseberries. Cyanidin 3-rutinoside has also been detected, but not quantified in, several different foods, such as rose hips, peach (var.), nectarines, garden rhubarbs, and asparagus. This could make cyanidin 3-rutinoside a potential biomarker for the consumption of these foods. A rutinoside consisting of cyanidin having the rutinosyl group at the 3-position.
Structure
Data?1563862128
Synonyms
ValueSource
Cyanidin 3-O-rhamnosylglucosideChEBI
Cyanidin 3-rhamnoglucosideChEBI
KeracyaninKegg
AntirrhininHMDB
CeracyaninHMDB
CyaninosideHMDB
Keracyanin, innHMDB
MeralopHMDB
NoctiluxHMDB
NyctaluxHMDB
OleocyaninHMDB
PrunicyaninHMDB
SambucinHMDB
SambucineHMDB
Cyanidin 3-rutinosideMeSH
Cyanidin-3-rutinosideMeSH
Chemical FormulaC27H31O15
Average Molecular Weight595.526
Monoisotopic Molecular Weight595.166295322
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
Traditional Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
CAS Registry Number28338-59-2
SMILES
[H][C@@]1(C)O[C@@]([H])(OC[C@@]2([H])O[C@@]([H])(OC3=CC4=C(C=C(O)C=C4O)[O+]=C3C3=CC(O)=C(O)C=C3)[C@]([H])(O)[C@@]([H])(O)[C@]2([H])O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O
InChI Identifier
InChI=1S/C27H30O15/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31)/p+1/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+/m0/s1
InChI KeyUSNPULRDBDVJAO-FXCAAIILSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentTertiary alcohols
Alternative Parents
Substituents
  • Tertiary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.9 g/LALOGPS
logP0.66ALOGPS
logP-0.64ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area252.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity147.13 m³·mol⁻¹ChemAxon
Polarizability56.93 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00pi-7290080000-4e9e17157d81edbbc7b2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00kk-7270009000-a677df67be0186eddbe9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000x-0090070000-125bca6d3508badde83fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0090080000-6c6a0d2425f4a8ce2dd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002u-0690200000-d0f495f57a6a08951ae3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001r-0090000000-5d9be53d8851211d98b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000x-0090050000-edf1f099fb6afbd7bdd4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001r-0090000000-3fbc8f30a8f68e2b6b12Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-50fc7a85af67b684d655Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090030000-6c1cc95884382202267aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090020000-af027bb2664bb06e30d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0211090000-99bd764f2c2a7dca281eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002g-0711090000-878065c4a8c8fed57e8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rb-6911010000-4f517c2e03a1ff30becfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-4421090000-61295fb4e486fff583fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ow-5911020000-3e796461f98c10c1e95fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0c04-9520000000-9e3f42b0650d9235dca8Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 10 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 10 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 10 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 10 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID56
FooDB IDFDB007049
KNApSAcK IDC00002376
Chemspider ID390288
KEGG Compound IDC08620
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAntirrhinin
METLIN IDNot Available
PubChem Compound441674
PDB IDNot Available
ChEBI ID28064
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.. .