ChemFOnt: Showing chemical card for Melilotoside (CFc000014665)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:03:29 UTC

Chemfont ID

CFc000014665

Molecule Identification

Common Name

Melilotoside

Definition

Melilotoside, also known as trans-beta-D-glucosyl-2-hydroxycinnamic acid or beta-D-glucosyl-2-coumarate, 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. Melilotoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Melilotoside is found in herbs and spices. Melilotoside has been isolated from Melilotus alba (white melilot), Melilotus altissimus (tall yellow sweet clover), and other plants.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-3-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate	Generator
Melilotoside	HMDB
trans-O-Coumarate 2-glucoside	Generator
cis-O-Coumarate 2-glucoside	Generator

Chemical Formula

C₁₅H₁₈O₈

Average Molecular Weight

326.2986

Monoisotopic Molecular Weight

326.100167552

IUPAC Name

(2E)-3-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

Traditional Name

melilotoside

CAS Registry Number

618-67-7

SMILES

OCC1OC(OC2=C(\C=C\C(O)=O)C=CC=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-2-1-3-8(9)5-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-5+

InChI Key

GVRIYIMNJGULCZ-AATRIKPKSA-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
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid
Coumaric acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Styrene
Phenol ether
Phenoxy compound
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Secondary alcohol
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Primary alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033581)
Cytoplasm (HMDB: HMDB0033581)

Source

Exogenous

Exogenous (HMDB: HMDB0033581)

Food

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.6 g/L	ALOGPS
logP	-0.7	ALOGPS
logP	-0.44	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.7	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.19 m³·mol⁻¹	ChemAxon
Polarizability	31.19 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

HMDB0303353

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016244

KNApSAcK ID

Not Available

Chemspider ID

10468576

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6275271

PDB ID

Not Available

ChEBI ID

172552

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Melilotoside (CFc000014665)

MOL for CFc000014665 (Melilotoside)

3D MOL for CFc000014665 (Melilotoside)

3D SDF for CFc000014665 (Melilotoside)

3D-SDF for CFc000014665 (Melilotoside)

PDB for CFc000014665 (Melilotoside)

3D PDB for CFc000014665 (Melilotoside)

SMILES for CFc000014665 (Melilotoside)

INCHI for CFc000014665 (Melilotoside)

Structure for CFc000014665 (Melilotoside)

3D Structure for CFc000014665 (Melilotoside)