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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:46:45 UTC
Update Date2019-08-01 17:55:54 UTC
HMDB IDHMDB0031946
Secondary Accession Numbers
  • HMDB31946
Metabolite Identification
Common NameO-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate
Description(Z)-N-[(4-hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside), also known as (4-methoxybenzyl)thiocarbamic acid 4'-O-(tri-O-acetyl-alpha-L-rhamnopyranoside), 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 (Z)-N-[(4-hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside) is a moderately basic compound (based on its pKa). Outside of the human body, (Z)-N-[(4-hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside) has been detected, but not quantified in, a few different foods, such as fats and oils, green vegetables, and herbs and spices. This could make (Z)-N-[(4-hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside) a potential biomarker for the consumption of these foods.
Structure
Data?1564682154
Synonyms
ValueSource
(2S,3R,4R,5S,6S)-4,5-Bis(acetyloxy)-2-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-6-methyloxan-3-yl acetic acidGenerator
(2S,3R,4R,5S,6S)-4,5-Bis(acetyloxy)-2-[4-({[ethoxy(sulphanyl)methylidene]amino}methyl)phenoxy]-6-methyloxan-3-yl acetateGenerator
(2S,3R,4R,5S,6S)-4,5-Bis(acetyloxy)-2-[4-({[ethoxy(sulphanyl)methylidene]amino}methyl)phenoxy]-6-methyloxan-3-yl acetic acidGenerator
(Z)-N-[(4-Hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside)HMDB
(Z)-N-[(4-Hydroxyphenyl)methyl]ethoxycarbothioamide 4’-(tri-acetylrhamnoside)HMDB
(Z)-O-Ethyl 4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(Z)-O-Ethyl 4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(Z)-O-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
(Z)-O-Ethyl-4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
N-[(4-Hydroxyphenyl)methyl]ethoxycarbothioamide 4'-(tri-acetylrhamnoside)HMDB
N-[(4-Hydroxyphenyl)methyl]ethoxycarbothioamide 4’-(tri-acetylrhamnoside)HMDB
O-Ethyl 4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
O-Ethyl 4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
O-Ethyl-4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamateHMDB
Chemical FormulaC22H29NO9S
Average Molecular Weight483.532
Monoisotopic Molecular Weight483.156302221
IUPAC Name(2S,3S,4R,5R,6S)-4,5-bis(acetyloxy)-6-(4-{[(ethoxymethanethioyl)amino]methyl}phenoxy)-2-methyloxan-3-yl acetate
Traditional Name(2S,3S,4R,5R,6S)-4,5-bis(acetyloxy)-6-(4-{[(ethoxymethanethioyl)amino]methyl}phenoxy)-2-methyloxan-3-yl acetate
CAS Registry Number147821-50-9
SMILES
CCOC(=S)NCC1=CC=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]2OC(C)=O)C=C1
InChI Identifier
InChI=1S/C22H29NO9S/c1-6-27-22(33)23-11-16-7-9-17(10-8-16)32-21-20(31-15(5)26)19(30-14(4)25)18(12(2)28-21)29-13(3)24/h7-10,12,18-21H,6,11H2,1-5H3,(H,23,33)/t12-,18-,19+,20+,21-/m0/s1
InChI KeyWYFYRQBBNVSDHV-CDEOHPBMSA-N
Chemical Taxonomy
DescriptionThis compound 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 Parents
Substituents
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Phenoxy compound
  • Phenol ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Thiocarbamic acid ester
  • Carboxylic acid ester
  • Thiocarbamic acid derivative
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Acetal
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organosulfur compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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
Water Solubility0.0052 g/LALOGPS
logP3.3ALOGPS
logP2.58ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area118.62 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity118.37 m³·mol⁻¹ChemAxon
Polarizability49.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3221900000-d7626e05bfc544532d9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-2364900000-668a7d33526369d69a31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-097l-0933100000-ffa54f9c26c164c352b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cdi-1943000000-1304a42dedd1aa89295fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9112700000-7f018ed0d9f8b9125b76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0r00-7439200000-ff0a4e77443d35797cdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-9320000000-7af0b411df2249abe32bSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008637
KNApSAcK IDNot Available
Chemspider ID8498489
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10323025
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .