Record Information |
---|
Version | 1.0 |
---|
Created at | 2024-05-11 04:36:15 UTC |
---|
Updated at | 2024-05-13 01:11:51 UTC |
---|
NP-MRD ID | NP0333121 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | Glucotropaeolin, potassium salt |
---|
Description | Glucotropeolin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Glucotropeolin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 2012 (PMID: 22305790). Based on a literature review a small amount of articles have been published on glucotropeolin (PMID: 24444907) (PMID: 27622707). |
---|
Structure | OC[C@H]1O[C@@H](S\C(CC2=CC=CC=C2)=N/OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C14H19NO9S2/c16-7-9-11(17)12(18)13(19)14(23-9)25-10(15-24-26(20,21)22)6-8-4-2-1-3-5-8/h1-5,9,11-14,16-19H,6-7H2,(H,20,21,22)/b15-10-/t9-,11-,12+,13-,14+/m1/s1 |
---|
Synonyms | Value | Source |
---|
Benzyl glucosinolate | ChEBI | Benzylglucosinolate | ChEBI | Glucotropaeolin | ChEBI | Benzyl glucosinolic acid | Generator | Benzylglucosinolic acid | Generator | Glucotropeolin, potassium salt | MeSH |
|
---|
Chemical Formula | C14H19NO9S2 |
---|
Average Mass | 409.4200 Da |
---|
Monoisotopic Mass | 409.05012 Da |
---|
IUPAC Name | {[(Z)-(2-phenyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene)amino]oxy}sulfonic acid |
---|
Traditional Name | glucotropeolin |
---|
CAS Registry Number | Not Available |
---|
SMILES | OC[C@H]1O[C@@H](S\C(CC2=CC=CC=C2)=N/OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O |
---|
InChI Identifier | InChI=1S/C14H19NO9S2/c16-7-9-11(17)12(18)13(19)14(23-9)25-10(15-24-26(20,21)22)6-8-4-2-1-3-5-8/h1-5,9,11-14,16-19H,6-7H2,(H,20,21,22)/b15-10-/t9-,11-,12+,13-,14+/m1/s1 |
---|
InChI Key | QQGLQYQXUKHWPX-RFEZBLSLSA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2024-05-11 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 300 MHz, D2O, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2024-05-11 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 300 MHz, D2O, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2024-05-11 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2024-05-11 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2024-05-11 | View Spectrum |
| Predicted Spectra |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 1H NMR Spectrum (1D, 300.13, D2O, simulated) | john.cort@pnnl.gov | Not Available | Not Available | 2024-05-11 | View Spectrum |
| Species |
---|
Species of Origin | Not Available |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic oxygen compounds |
---|
Class | Organooxygen compounds |
---|
Sub Class | Carbohydrates and carbohydrate conjugates |
---|
Direct Parent | Alkylglucosinolates |
---|
Alternative Parents | |
---|
Substituents | - Alkylglucosinolate
- Glycosyl compound
- S-glycosyl compound
- Monocyclic benzene moiety
- Oxane
- Benzenoid
- Monothioacetal
- Organic sulfuric acid or derivatives
- Secondary alcohol
- Sulfenyl compound
- Polyol
- Oxacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Primary alcohol
- Organic oxide
- Organosulfur compound
- Organonitrogen compound
- Alcohol
- Organopnictogen compound
- Organic nitrogen compound
- Aromatic heteromonocyclic compound
|
---|
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 | - Li ZY, Wang Y, Shen WT, Zhou P: Content determination of benzyl glucosinolate and anti-cancer activity of its hydrolysis product in Carica papaya L. Asian Pac J Trop Med. 2012 Mar;5(3):231-3. doi: 10.1016/S1995-7645(12)60030-3. [PubMed:22305790 ]
- Ares AM, Nozal MJ, Bernal JL, Bernal J: Optimized extraction, separation and quantification of twelve intact glucosinolates in broccoli leaves. Food Chem. 2014;152:66-74. doi: 10.1016/j.foodchem.2013.11.125. Epub 2013 Nov 28. [PubMed:24444907 ]
- Guzman-Perez V, Bumke-Vogt C, Schreiner M, Mewis I, Borchert A, Pfeiffer AF: Benzylglucosinolate Derived Isothiocyanate from Tropaeolum majus Reduces Gluconeogenic Gene and Protein Expression in Human Cells. PLoS One. 2016 Sep 13;11(9):e0162397. doi: 10.1371/journal.pone.0162397. eCollection 2016. [PubMed:27622707 ]
|
---|