ChemFOnt: Showing chemical card for O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate (CFc000013126)

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

CFc000013126

Molecule Identification

Common Name

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

Definition

O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate is a fully acetylated carbamate 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 the carbonyl group.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
O-Methyl-4-[(2',3',4'-tri-O-acetyl-a-L-rhamnosyloxy)benzyl]carbamate	Generator
O-Methyl-4-[(2',3',4'-tri-O-acetyl-a-L-rhamnosyloxy)benzyl]carbamic acid	Generator
O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamic acid	Generator
O-Methyl-4-[(2',3',4'-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]carbamate	Generator
O-Methyl-4-[(2',3',4'-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]carbamic acid	Generator
N-[(4-{[(2S,3R,4R,5S,6S)-3,4,5-tris(acetyloxy)-6-methyloxan-2-yl]oxy}phenyl)methyl]methoxycarboximidate	HMDB
(e)-O-Methyl 4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate	HMDB
(e)-O-Methyl 4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]carbamate	HMDB
(e)-O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate	HMDB
(e)-O-Methyl-4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]carbamate	HMDB
(Z)-O-Methyl 4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate	HMDB
(Z)-O-Methyl 4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]carbamate	HMDB
(Z)-O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate	HMDB
(Z)-O-Methyl-4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]carbamate	HMDB
O-Methyl 4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate	HMDB
O-Methyl 4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]carbamate	HMDB
O-Methyl-4-[(2’,3’,4’-tri-O-acetyl-α-L-rhamnosyloxy)benzyl]carbamate	HMDB
O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate	HMDB

Chemical Formula

C₂₁H₂₇NO₁₀

Average Molecular Weight

453.444

Monoisotopic Molecular Weight

453.163496073

IUPAC Name

(2S,3S,4R,5R,6S)-4,5-bis(acetyloxy)-6-(4-{[(methoxycarbonyl)amino]methyl}phenoxy)-2-methyloxan-3-yl acetate

Traditional Name

(2S,3S,4R,5R,6S)-4,5-bis(acetyloxy)-6-(4-{[(methoxycarbonyl)amino]methyl}phenoxy)-2-methyloxan-3-yl acetate

CAS Registry Number

163812-18-8

SMILES

COC(=O)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/C21H27NO10/c1-11-17(29-12(2)23)18(30-13(3)24)19(31-14(4)25)20(28-11)32-16-8-6-15(7-9-16)10-22-21(26)27-5/h6-9,11,17-20H,10H2,1-5H3,(H,22,26)/t11-,17-,18+,19+,20-/m0/s1

InChI Key

LCQPFOZNYVLABG-FXCHBBSNSA-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

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Tricarboxylic acid or derivatives
Phenol ether
Phenoxy compound
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Methylcarbamate
Carbamic acid ester
Carboxylic acid ester
Carbonic acid derivative
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031948)
Cytoplasm (HMDB: HMDB0031948)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031948)

Source

Exogenous

Food

Food (HMDB: HMDB0031948)

Exogenous (HMDB: HMDB0031948)

Endogenous

Plant

Plant (HMDB: HMDB0031948)

Endogenous (HMDB: HMDB0031948)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.44 g/L	ALOGPS
logP	2.21	ALOGPS
logP	1.34	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.72	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	135.69 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	105.63 m³·mol⁻¹	ChemAxon
Polarizability	45.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031948

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031412

KNApSAcK ID

Not Available

Chemspider ID

103885349

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101919834

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate (CFc000013126)

MOL for CFc000013126 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate)

3D MOL for CFc000013126 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate)

3D SDF for CFc000013126 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate)

3D-SDF for CFc000013126 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate)

PDB for CFc000013126 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate)

3D PDB for CFc000013126 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate)

SMILES for CFc000013126 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate)

INCHI for CFc000013126 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate)

Structure for CFc000013126 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate)

3D Structure for CFc000013126 (O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate)