Record Information |
---|
Version | 1.0 |
---|
Created at | 2020-11-23 19:43:22 UTC |
---|
Updated at | 2021-08-12 19:52:29 UTC |
---|
NP-MRD ID | NP0002908 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | Phenyl beta-D-glucoside |
---|
Provided By | BMRB![BMRB logo](/attributions/logo_bmrb.svg) |
---|
Description | Phenyl 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 | OC[C@H]1O[C@@H](OC2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O 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 |
---|
Synonyms | Value | Source |
---|
Phenylglucoside | Kegg | Phenyl b-D-glucopyranoside | Generator | Phenyl β-D-glucopyranoside | Generator | Phenyl-beta-glucoside | MeSH | Phenylglucoside, (alpha-(D))-isomer | MeSH | Phenylglucoside, (alpha-(L))-isomer | MeSH |
|
---|
Chemical Formula | C12H16O6 |
---|
Average Mass | 256.2540 Da |
---|
Monoisotopic Mass | 256.09469 Da |
---|
IUPAC Name | (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol |
---|
Traditional Name | phenyl β-D-glucoside |
---|
CAS Registry Number | Not 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 Key | NEZJDVYDSZTRFS-RMPHRYRLSA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 500 MHz, methanol, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, methanol, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, methanol, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, methanol, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic oxygen compounds |
---|
Class | Organooxygen compounds |
---|
Sub Class | Carbohydrates and carbohydrate conjugates |
---|
Direct Parent | Phenolic glycosides |
---|
Alternative Parents | Not Available |
---|
Substituents | Not Available |
---|
Molecular Framework | Aromatic heteromonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
|
---|