Showing Compound Card for Isovitexin-7-o-rhamnoglucoside (CDB000339)

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Record Information
Version1.0
Created at2020-03-19 00:31:46 UTC
Updated at2020-11-18 16:35:04 UTC
CannabisDB IDCDB000339
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameIsovitexin-7-o-rhamnoglucoside
DescriptionIsovitexin-7-O-rhamnoglucoside belongs to the class of organic compounds known as flavonoid O-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2- or 7-position of the phenylchromen-4-one flavonoid backbone. Thus, Isovitexin-7-O-glucoside consists of the apigenin flavanoid with a 1,5-anhydro-D-glucitol group at the C-6 position of apigenin linked to rhamnose at the O-7 position of apigenin. Isovitexin-7-O-rhamnoglucoside is a derivative of isovitexin. Isovitexin is a C-glycosylated polyphenol that can be found in the passionflower, Cannabis, and the açaí palm. Isovitexin can have a number of sugar moieties attached to it, including glucose (leading to Isovitexin 7-O-glucoside, Isovitexin 7,2"-di-O-glucoside, Isovitexin C-glucoside) and rhamnose (leading to Isovitexin 7-rhamnoglucoside). Isovitexin-7-O-rhamnoglucoside is one of everal 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 FormulaC33H40O19
Average Molecular Weight740.66
Monoisotopic Molecular Weight740.2164
IUPAC Name7-{[(2R,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
Traditional Name7-{[(2R,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
CAS Registry NumberNot Available
SMILES
C[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)C=C(O3)C3=CC=C(O)C=C3)C(O)=C2[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C33H40O19/c1-10-21(38)25(42)29(46)32(47-10)52-31-27(44)23(40)18(9-35)51-33(31)50-16-7-15-19(13(37)6-14(48-15)11-2-4-12(36)5-3-11)24(41)20(16)30-28(45)26(43)22(39)17(8-34)49-30/h2-7,10,17-18,21-23,25-36,38-46H,8-9H2,1H3/t10-,17-,18+,21-,22-,23+,25-,26+,27+,28+,29+,30+,31+,32-,33+/m1/s1
InChI KeyPSNRLITVALDHGL-CWJBGNNISA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Not Available
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-0.71ALOGPS
logP-3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)6.87ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area315.21 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity169.05 m³·mol⁻¹ChemAxon
Polarizability71.7 ųChemAxon
Number of Rings6ChemAxon
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 ]