Apigenin 7-O-beta-D-rutinoside (CHEM026507)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:01:45 UTC
Update Date2016-11-09 01:18:17 UTC
Accession NumberCHEM026507
Identification
Common NameApigenin 7-O-beta-D-rutinoside
ClassSmall Molecule
DescriptionAn apigenin derivative having an alpha-(1->2)-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety attached to the 7-hydroxy group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-oneChEBI
Apigenin-7-O-rhamnoglucosideChEBI
RhoifolinChEBI
RhoifolosideChEBI
7-((2-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-oneGenerator
7-((2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-oneGenerator
Apigenin 7-O-b-D-rutinosideGenerator
Apigenin 7-O-β-D-rutinosideGenerator
Chemical FormulaC27H30O14
Average Molecular Mass578.519 g/mol
Monoisotopic Mass578.164 g/mol
CAS Registry NumberNot Available
IUPAC Name7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Namerhoifolin
SMILESC[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC3=C(C(O)=C2)C(=O)C=C(O3)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O
InChI IdentifierInChI=1S/C27H30O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-8,10,18,20-30,32-36H,9H2,1H3/t10-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
InChI KeyRPMNUQRUHXIGHK-PYXJVEIZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • Hydroxyflavonoid
  • Flavone
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Phenolic glycoside
  • Chromone
  • Glycosyl compound
  • Disaccharide
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility2.55 g/LALOGPS
logP0ALOGPS
logP-0.29ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)8.31ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area225.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity135.93 m³·mol⁻¹ChemAxon
Polarizability56.74 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-002r-0905000000-7987816fb8648b0eea18Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-002r-0905000000-7987816fb8648b0eea18Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-002r-0905000000-7987816fb8648b0eea18Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0000092000-fe08120bacfe47df17f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0000092000-fe08120bacfe47df17f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-004i-0000092000-fe08120bacfe47df17f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 40V, positivesplash10-001i-0000900000-0e57f1f59429661a74d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 40V, positivesplash10-00di-0090000000-99129ef4591876751de6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0290750000-55a6ae16cf519467ed4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0190300000-06d3ee053e5687568b07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1390100000-f2c461f6351166e6fd45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02vi-4482980000-bf876ac84a2dcad10a60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2591410000-6e87958379dbe1b68313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-6490000000-3ea18c33c05e3b5b5b90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-0090040000-5360a5a561c2a6bbb4a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00f0-0090910000-02c6a8c796e474e00fb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0090000000-60b322ff74af8a765580Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000190000-48e73583084c06ab4561Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00pi-0050790000-9b843f6502778be0c2e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0090010000-76c066300921436abb72Spectrum
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 IDHMDB0303149
FooDB IDFDB007976
Phenol Explorer IDNot Available
KNApSAcK IDC00004157
BiGG IDNot Available
BioCyc IDAPIGENIN-7-O-NEOHESPERIDOSIDE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRhoifolin
Chemspider ID4445347
ChEBI ID31227
PubChem Compound IDNot Available
Kegg Compound IDC12627
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15631081
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15974126
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19771866
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20222420