ChemFOnt: Showing chemical card for 4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate (CFc000013905)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:02:25 UTC

Chemfont ID

CFc000013905

Molecule Identification

Common Name

4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate

Definition

4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate is a glucosinolate that has been isolated from the seeds and leaves of Moringa oleifera (horseradish tree) and the seeds of Moringa peregrina. It is also found in herbs and spices.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Hydroxybenzyl isothiocyanic acid 4''-acetylrhamnoside	Generator
4,5-Dihydroxy-6-[4-(isothiocyanatomethyl)phenoxy]-2-methyloxan-3-yl acetic acid	Generator

Chemical Formula

C₁₆H₁₉NO₆S

Average Molecular Weight

353.39

Monoisotopic Molecular Weight

353.093308035

IUPAC Name

4,5-dihydroxy-6-[4-(isothiocyanatomethyl)phenoxy]-2-methyloxan-3-yl acetate

Traditional Name

4,5-dihydroxy-6-[4-(isothiocyanatomethyl)phenoxy]-2-methyloxan-3-yl acetate

CAS Registry Number

73255-41-1

SMILES

CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O)C1OC(C)=O

InChI Identifier

InChI=1S/C16H19NO6S/c1-9-15(22-10(2)18)13(19)14(20)16(21-9)23-12-5-3-11(4-6-12)7-17-8-24/h3-6,9,13-16,19-20H,7H2,1-2H3

InChI Key

WVUZLAMBBZISKM-UHFFFAOYSA-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
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
1,2-diol
Carboxylic acid ester
Isothiocyanate
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organosulfur compound
Organic nitrogen 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: HMDB0032802)
Cytoplasm (HMDB: HMDB0032802)

Source

Exogenous

Exogenous (HMDB: HMDB0032802)

Food

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	2.37	ALOGPS
logP	1.71	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.26	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.58 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.67 m³·mol⁻¹	ChemAxon
Polarizability	36.17 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

HMDB0032802

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010774

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22718840

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate (CFc000013905)

MOL for CFc000013905 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

3D MOL for CFc000013905 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

3D SDF for CFc000013905 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

3D-SDF for CFc000013905 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

PDB for CFc000013905 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

3D PDB for CFc000013905 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

SMILES for CFc000013905 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

INCHI for CFc000013905 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

Structure for CFc000013905 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

3D Structure for CFc000013905 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)