Showing Compound Card for Orientin-7-o-glucoside (CDB000341)

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Record Information
Version1.0
Created at2020-03-19 00:31:53 UTC
Updated at2020-12-07 19:07:22 UTC
CannabisDB IDCDB000341
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameOrientin-7-o-glucoside
DescriptionOrientin-7-O-glucoside or Orientin-7-glucoside is a derivative of the flavone known as Orientin. It 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. Thus, orientin 7-O-glucoside consists of a luteolin flavonoid backbone with a glucose ring attached at the 8-C position and glucose attached at the O-7 position. Orientin-7-O-glucoside is quite water soluble due to the attachment of several sugar moieties. Orientin-7-O-glucoside Orientin is a water-soluble flavonoid C-glycoside found in calcium tree and black bamboo. Orientin has been detected, but not quantified in, several different foods, such as spelts, triticales, red rices, hard wheats, and flaxseeds. Orientin is also found in the passionflower, the Açaí palm, buckwheat sprouts, and in millets. Orientin exhibits antioxidant, antiaging, antiviral, antibacterial, anti-inflammation, vasodilatation and cardioprotective, radiation protective, neuroprotective, antidepressant-like, antiadipogenesis, and antinociceptive activities ( Ref:DOI ). Orientin can have a number of sugar moieties attached to it, including rhamnose (leading to Orientin-7-O-rhamnoglucoside) and glucose (leading to Orientin-7-O-glucoside). Orientin-7-O-glucoside is one of several dozen flavonoid glycosides that are known in cannabis plants. It was first isolated and identified as a cannabis constituent in 1973 (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC27H30O16
Average Molecular Weight610.52
Monoisotopic Molecular Weight610.1534
IUPAC Name2-(3,4-dihydroxyphenyl)-5-hydroxy-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Name2-(3,4-dihydroxyphenyl)-5-hydroxy-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C27H30O16/c28-6-15-19(34)21(36)23(38)26(41-15)18-14(42-27-24(39)22(37)20(35)16(7-29)43-27)5-12(33)17-11(32)4-13(40-25(17)18)8-1-2-9(30)10(31)3-8/h1-5,15-16,19-24,26-31,33-39H,6-7H2/t15-,16+,19+,20+,21-,22-,23+,24+,26-,27+/m0/s1
InChI KeySPAHGZOYBCREJA-XJHXITLBSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Role

Industrial application:

Biological role:

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-0.99ALOGPS
logP-2.6ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)7.24ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area276.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity140.16 m³·mol⁻¹ChemAxon
Polarizability58.18 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 ]