Showing Compound Card for 2"-o-Glucopyranosylorientin (CDB000790)

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Record Information
Version1.0
Created at2020-03-19 00:57:08 UTC
Updated at2020-12-07 19:07:45 UTC
CannabisDB IDCDB000790
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2"-o-Glucopyranosylorientin
Description2"-O-Glucopyranosylorientin, belongs to the class of organic compounds known as flavonoid 8-O-glycosides. Flavonoid 8-O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to a specific position of a 2-phenylchromen-4-one flavonoid backbone. 2"-O-glucopyranosylorientin is a glucopyranose derivative of the flavonoid known as orientin. Orientin is the 8-C glucoside of luteolin and is found in passion flower, bamboo, the Açaí palm, buckwheat sprouts, and in millets. 2"-O-Glucopyranosylorientin was first identified in cannabis in the 1970s (PMID: 6991645 ). Orientin and its derivatives are known to have antioxidant, anti-aging, antiviral, antibacterial, anti-inflammatory, neuroprotective, antiadipogenic, vasodilatory and cardioprotective effects (PMID: 27298620 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC27H30O16
Average Molecular Weight610.52
Monoisotopic Molecular Weight610.1534
IUPAC Name8-[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
Traditional Name8-[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
CAS Registry NumberNot Available
SMILES
OC[C@@H]1O[C@H](O[C@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]2C2=C(O)C=C(O)C3=C2OC(=CC3=O)C2=CC=C(O)C(O)=C2)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C27H30O16/c28-6-15-20(36)22(38)26(43-27-23(39)21(37)19(35)16(7-29)42-27)25(41-15)18-12(33)4-11(32)17-13(34)5-14(40-24(17)18)8-1-2-9(30)10(31)3-8/h1-5,15-16,19-23,25-33,35-39H,6-7H2/t15-,16+,19-,20-,21-,22+,23+,25-,26+,27-/m1/s1
InChI KeyQQBFHNKJGBCSLG-HXTZOUIPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • Hydroxyflavonoid
  • Flavone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Phenolic glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Chromone
  • C-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Dialkyl ether
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.63ALOGPS
logP-2.1ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)6.17ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area276.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity140.43 m³·mol⁻¹ChemAxon
Polarizability56.71 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Lam KY, Ling AP, Koh RY, Wong YP, Say YH: A Review on Medicinal Properties of Orientin. Adv Pharmacol Sci. 2016;2016:4104595. doi: 10.1155/2016/4104595. Epub 2016 May 19. [PubMed:27298620 ]