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Record Information
Version2.0
Created at2022-09-12 14:14:16 UTC
Updated at2022-09-12 14:14:16 UTC
NP-MRD IDNP0329653
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3r,4s,5s,6r)-2-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-6-({[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol
DescriptionGeranyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside, also known as GXPGP, belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (2r,3r,4s,5s,6r)-2-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-6-({[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol is found in Camellia sinensis. (2r,3r,4s,5s,6r)-2-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-6-({[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol was first documented in 1993 (PMID: 7763947). Based on a literature review very few articles have been published on Geranyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside (PMID: 11833622).
Structure
Thumb
Synonyms
ValueSource
Geranyl 6-O-b-D-xylopyranosyl-b-D-glucopyranosideGenerator
Geranyl 6-O-β-D-xylopyranosyl-β-D-glucopyranosideGenerator
GXPGPMeSH
Geranyl 6-O-xylopyranosyl-glucopyranosideMeSH
Chemical FormulaC21H36O10
Average Mass448.5090 Da
Monoisotopic Mass448.23085 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CC(C)=CCC\C(C)=C\CO[C@@H]1O[C@H](CO[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C21H36O10/c1-11(2)5-4-6-12(3)7-8-28-21-19(27)17(25)16(24)14(31-21)10-30-20-18(26)15(23)13(22)9-29-20/h5,7,13-27H,4,6,8-10H2,1-3H3/b12-7+/t13-,14-,15+,16-,17+,18-,19-,20+,21-/m1/s1
InChI KeyIEGFOTASSBZIBZ-QLPUMLPOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Camellia sinensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTerpene glycosides
Alternative Parents
Substituents
  • Terpene glycoside
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Fatty acyl
  • Oxane
  • Secondary alcohol
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00060053
Chemspider ID4947659
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6443689
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sekiwa Y, Kobayashi A, Kubota K, Takenaka M: First isolation of geranyl disaccharides from ginger and their relations to aroma formation. Nat Prod Lett. 2001;15(4):267-74. doi: 10.1080/10575630108041291. [PubMed:11833622 ]
  2. Guo W, Sakata K, Watanabe N, Nakajima R, Yagi A, Ina K, Luo S: Geranyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside isolated as an aroma precursor from tea leaves for oolong tea. Phytochemistry. 1993 Aug;33(6):1373-5. doi: 10.1016/0031-9422(93)85093-7. [PubMed:7763947 ]
  3. LOTUS database [Link]