Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2020-11-23 19:43:22 UTC
Updated at2021-08-12 19:52:29 UTC
NP-MRD IDNP0002908
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhenyl beta-D-glucoside
Provided ByBMRBBMRB logo
DescriptionPhenyl beta-D-glucopyranoside, also known as phenylglucoside, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Phenyl beta-D-glucoside is found in Gymnadenia conopsea. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on Phenyl beta-D-glucopyranoside (PMID: 34162137) (PMID: 33843220) (PMID: 33477839) (PMID: 32950870).
Structure
Thumb
Synonyms
ValueSource
PhenylglucosideKegg
Phenyl b-D-glucopyranosideGenerator
Phenyl β-D-glucopyranosideGenerator
Phenyl-beta-glucosideMeSH
Phenylglucoside, (alpha-(D))-isomerMeSH
Phenylglucoside, (alpha-(L))-isomerMeSH
Chemical FormulaC12H16O6
Average Mass256.2540 Da
Monoisotopic Mass256.09469 Da
IUPAC Name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol
Traditional Namephenyl β-D-glucoside
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OC2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C12H16O6/c13-6-8-9(14)10(15)11(16)12(18-8)17-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9-,10+,11-,12-/m1/s1
InChI KeyNEZJDVYDSZTRFS-RMPHRYRLSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, methanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, methanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, methanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, methanol, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Gymnadenia conopseaLOTUS Database
Gymnadenia conopsea R.BR.KNApSAcK Database
Triticum aestivumKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic 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
logP-0.64ALOGPS
logP-0.6ChemAxon
logS-0.73ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.18 m³·mol⁻¹ChemAxon
Polarizability24.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00030988
Chemspider ID58590
KEGG Compound IDC11611
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Liu FY, Wen J, Hou J, Zhang SQ, Sun CB, Zhou LC, Yin W, Pang WL, Wang C, Ying Y, Han SS, Yan JY, Li CX, Yuan JL, Xing HJ, Yang ZS: Gastrodia remodels intestinal microflora to suppress inflammation in mice with early atherosclerosis. Int Immunopharmacol. 2021 Jul;96:107758. doi: 10.1016/j.intimp.2021.107758. Epub 2021 May 24. [PubMed:34162137 ]
  3. Chen X, Fedrizzi B, Kilmartin PA, Quek SY: Free and Glycosidic Volatiles in Tamarillo (Solanum betaceum Cav. syn. Cyphomandra betacea Sendt.) Juices Prepared from Three Cultivars Grown in New Zealand. J Agric Food Chem. 2021 Apr 21;69(15):4518-4532. doi: 10.1021/acs.jafc.1c00837. Epub 2021 Apr 11. [PubMed:33843220 ]
  4. Cebrian-Tarancon C, Oliva J, Camara MA, Alonso GL, Salinas MR: Analysis of Intact Glycosidic Aroma Precursors in Grapes by High-Performance Liquid Chromatography with a Diode Array Detector. Foods. 2021 Jan 19;10(1). pii: foods10010191. doi: 10.3390/foods10010191. [PubMed:33477839 ]
  5. Voelker AL, Felten C, Taylor LS, Mauer LJ: Effects of polyphenols on crystallization of amorphous sucrose lyophiles. Food Chem. 2021 Feb 15;338:128061. doi: 10.1016/j.foodchem.2020.128061. Epub 2020 Sep 14. [PubMed:32950870 ]