Record Information
Version1.0
Creation date2010-04-08 22:12:34 UTC
Update date2019-11-26 03:13:35 UTC
Primary IDFDB016667
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameKaempferol 3-rutinoside
DescriptionBiorobin, also known as kaempferol 3-robinobioside, is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Biorobin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Biorobin can be found in herbs and spices and pulses, which makes biorobin a potential biomarker for the consumption of these food products.
CAS Number17650-84-9
Structure
Thumb
Synonyms
SynonymSource
Kaempferol 3-robinobiosideHMDB
Kaempferol-3-O-rutinosideMeSH, HMDB
Kaempferol 3-O-beta-D-rutinosidebiospider
Kaempferol 3-rutinosidedb_source
Kaempferol-3-rutinosidebiospider
Nicotiflorindb_source
Nicotiflorosidedb_source
Nictoflorin (incorr.)db_source
Predicted Properties
PropertyValueSource
Water Solubility3.07 g/LALOGPS
logP0.07ALOGPS
logP-0.57ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area245.29 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity138.16 m³·mol⁻¹ChemAxon
Polarizability56.89 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H30O15
IUPAC name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-4-one
InChI IdentifierInChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3
InChI KeyRTATXGUCZHCSNG-UHFFFAOYSA-N
Isomeric SMILESCC1OC(OCC2OC(OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC=C(O)C=C3)C(O)C(O)C2O)C(O)C(O)C1O
Average Molecular Weight594.5181
Monoisotopic Molecular Weight594.15847029
Classification
Description Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-3-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Oxane
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.55%; H 5.09%; O 40.37%DFC
Melting PointMp 190-192°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -52 (c, 1 in Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSKaempferol 3-robinobioside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056r-7581190000-1db708a48c07e5637984Spectrum
Predicted GC-MSKaempferol 3-robinobioside, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-9625108000-1e3b732a8f92be43f074Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0190170000-b90efd1b6ecce3f8a53d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190100000-10b192f39eaf18eda6d82015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1590000000-40e8403c5aa772e194522015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0190170000-b90efd1b6ecce3f8a53d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190100000-10b192f39eaf18eda6d82015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1590000000-40e8403c5aa772e194522015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0190170000-b90efd1b6ecce3f8a53d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190100000-10b192f39eaf18eda6d82015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1590000000-40e8403c5aa772e194522015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0190170000-b90efd1b6ecce3f8a53d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190100000-10b192f39eaf18eda6d82015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1590000000-40e8403c5aa772e194522015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0190170000-b90efd1b6ecce3f8a53d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190100000-10b192f39eaf18eda6d82015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1590000000-40e8403c5aa772e194522015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-3480390000-8523e2f778c6f46a1c902015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2490010000-f22c1567c9d1647abb822015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2490000000-4514129aceb63ecf768b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-3480390000-8523e2f778c6f46a1c902015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2490010000-f22c1567c9d1647abb822015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2490000000-4514129aceb63ecf768b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-3480390000-8523e2f778c6f46a1c902015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2490010000-f22c1567c9d1647abb822015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2490000000-4514129aceb63ecf768b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-3480390000-8523e2f778c6f46a1c902015-04-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5318767
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID320
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFG98-E:KSH83-J
EAFUS IDNot Available
Dr. Duke IDKAEMPFEROL-3-O-RUTINOSIDE|KAEMPFEROL-3-0-RUTINOSIDE|KAEMPFEROL-3-O-BETA-D-RUTINOSIDE|KAEMPFEROL-3-O-BETA-D-RUTOSIDE|KAEMPFEROL-3-O-BETA-RUTINOSIDE|NICOTIFLORIN
BIGG IDNot Available
KNApSAcK IDC00005169
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 IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
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.