Showing chemical card for O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate (CFc000013121)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:01:24 UTC

Chemfont ID

CFc000013121

Molecule Identification

Common Name

O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate

Definition

O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate is a fully acetylated thiocarbamate glycoside. It has been isolated from the leaves of Moringa oleifera (horseradish tree). It is found in fats and oils, herbs and spices, and green vegetables. The trans and cis rotamers differ in the orientation of the NH group with respect to sulfur.

Structure

MOL SDF PDB SMILES InChI

MOL for CFc000013121 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate)

Download

3D MOL for CFc000013121 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate)

Download

3D SDF for CFc000013121 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate)

Download

3D-SDF for CFc000013121 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate)

Download

PDB for CFc000013121 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate)

Download

3D PDB for CFc000013121 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate)

Download

SMILES for CFc000013121 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate)

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

Download

INCHI for CFc000013121 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate)

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

Download

Structure for CFc000013121 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate)

Download

3D Structure for CFc000013121 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate)

Synonyms

Value	Source
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-a-L-rhamnosyloxy)benzyl]thiocarbamate	Generator
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-a-L-rhamnosyloxy)benzyl]thiocarbamic acid	Generator
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamic acid	Generator
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamate	Generator
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamic acid	Generator
(2S,3R,4R,5S,6S)-4,5-Bis(acetyloxy)-2-[4-({[ethoxy(sulfanyl)methylidene]amino}methyl)phenoxy]-6-methyloxan-3-yl acetic acid	Generator, HMDB
(2S,3R,4R,5S,6S)-4,5-Bis(acetyloxy)-2-[4-({[ethoxy(sulphanyl)methylidene]amino}methyl)phenoxy]-6-methyloxan-3-yl acetate	Generator, HMDB
(2S,3R,4R,5S,6S)-4,5-Bis(acetyloxy)-2-[4-({[ethoxy(sulphanyl)methylidene]amino}methyl)phenoxy]-6-methyloxan-3-yl acetic acid	Generator, HMDB
(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]thiocarbamate	HMDB
(Z)-O-Ethyl 4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB
(Z)-O-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB
(Z)-O-Ethyl-4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB
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]thiocarbamate	HMDB
O-Ethyl 4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB
O-Ethyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB
O-Ethyl-4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]thiocarbamate	HMDB

Chemical Formula

C₂₂H₂₉NO₉S

Average Molecular Weight

483.532

Monoisotopic Molecular Weight

483.156302221

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 Number

147821-48-5

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 Key

WYFYRQBBNVSDHV-CDEOHPBMSA-N

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

Hexoses
O-glycosyl compounds
Tricarboxylic acids and derivatives
Phenoxy compounds
Phenol ethers
Oxanes
Thiocarbamic acid esters
Carboxylic acid esters
Oxacyclic compounds
Acetals
Organopnictogen compounds
Organonitrogen compounds
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031943)
Cell membrane (HMDB: HMDB0031943)

Source

Endogenous

Endogenous (HMDB: HMDB0031943)

Exogenous

Food

Food (HMDB: HMDB0031943)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0031943)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0078 g/L	ALOGPS
logP	3.3	ALOGPS
logP	2.58	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	118.62 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	118.37 m³·mol⁻¹	ChemAxon
Polarizability	49.7 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031946

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008637

KNApSAcK ID

Not Available

Chemspider ID

8498489

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10323025

PDB ID

Not Available

ChEBI ID

172709

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available