Cannabis Compound Database: Showing Compound Card for cis-Melilotoside (CDB005057)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Created at

2020-04-17 19:04:59 UTC

Updated at

2020-11-18 16:39:15 UTC

CannabisDB ID

CDB005057

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

cis-Melilotoside

Description

cis-beta-D-Glucosyl-2-hydroxycinnamate, also known as beta-D-glucosyl-2-coumarinic acid or cis-coumarinic acid-beta-D-glucoside, 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. cis-beta-D-Glucosyl-2-hydroxycinnamate is an extremely weak basic (essentially neutral) compound (based on its pKa). cis-beta-D-Glucosyl-2-hydroxycinnamate exists in all living organisms, ranging from bacteria to humans. Outside of the human body, cis-beta-D-Glucosyl-2-hydroxycinnamate has been detected, but not quantified in, several different foods, such as chinese broccoli, european cranberries, black chokeberries, grapefruit/pummelo hybrids, and cardoons. This could make cis-beta-D-glucosyl-2-hydroxycinnamate a potential biomarker for the consumption of these foods. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. cis-Melilotoside is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2Z)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]acrylic acid	ChEBI
beta-D-Glucosyl-2-coumarinate	ChEBI
beta-D-Glucosyl-2-coumarinic acid	ChEBI
cis-beta-D-Glucosyl-2-hydroxycinnamic acid	ChEBI
cis-Coumarinic acid-beta-D-glucoside	ChEBI
cis-Melilotoside	ChEBI
(2Z)-3-[2-(b-D-Glucopyranosyloxy)phenyl]acrylate	Generator
(2Z)-3-[2-(b-D-Glucopyranosyloxy)phenyl]acrylic acid	Generator
(2Z)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]acrylate	Generator
(2Z)-3-[2-(β-D-Glucopyranosyloxy)phenyl]acrylate	Generator
(2Z)-3-[2-(β-D-Glucopyranosyloxy)phenyl]acrylic acid	Generator
cis-Coumarinate-β-D-glucoside	Generator
b-D-Glucosyl-2-coumarinate	Generator
b-D-Glucosyl-2-coumarinic acid	Generator
β-D-Glucosyl-2-coumarinate	Generator
β-D-Glucosyl-2-coumarinic acid	Generator
cis-b-D-Glucosyl-2-hydroxycinnamate	Generator
cis-b-D-Glucosyl-2-hydroxycinnamic acid	Generator
cis-beta-D-Glucosyl-2-hydroxycinnamate	Generator
cis-β-D-Glucosyl-2-hydroxycinnamate	Generator
cis-β-D-Glucosyl-2-hydroxycinnamic acid	Generator
cis-Coumarinate-b-D-glucoside	Generator
cis-Coumarinate-beta-D-glucoside	Generator
cis-Coumarinic acid-b-D-glucoside	Generator
cis-Coumarinic acid-β-D-glucoside	Generator
(2Z)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
(2Z)-3-[2-(β-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
2'-(beta-D-Glucopyranosyloxy)cinnamic acid	HMDB
2'-(β-D-Glucopyranosyloxy)cinnamic acid	HMDB
2’-(β-D-Glucopyranosyloxy)cinnamic acid	HMDB
3-[2-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
3-[2-(β-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
Coumarin glucoside	HMDB
Coumarinate glucoside	HMDB
Coumarinic acid glucoside	HMDB
beta-D-Glucosyl-2-coumarate	HMDB
beta-D-Glucosyl-2-coumaric acid	HMDB
cis-o-Hydroxycinnamic acid glucoside	HMDB
o-(Glucosyloxy)cinnamic acid	HMDB
o-Coumaroyl beta-D-glucopyranoside	HMDB
o-Coumaroyl β-D-glucopyranoside	HMDB
β-D-Glucosyl-2-coumarate	HMDB
β-D-Glucosyl-2-coumaric acid	HMDB

Chemical Formula

C₁₅H₁₈O₈

Average Molecular Weight

326.3

Monoisotopic Molecular Weight

326.1002

IUPAC Name

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

Traditional Name

cis-melilotoside

CAS Registry Number

2446-60-8

SMILES

OC[C@H]1O[C@@H](OC2=C(\C=C/C(O)=O)C=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

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-/t10-,12-,13+,14-,15-/m1/s1

InChI Key

GVRIYIMNJGULCZ-QLFWQTQQSA-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

beta-D-glucoside (CHEBI:62251 )
Monolignols (C05839 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.7	ALOGPS
logP	-0.44	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.2	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	31.48 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	cis-Melilotoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0zfr-5943000000-c492ad4cea7748c10d1d	Spectrum
Predicted GC-MS	cis-Melilotoside, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-1020229000-cd5e122c29a7c414bbb3	Spectrum
Predicted GC-MS	cis-Melilotoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	cis-Melilotoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0aos-0937000000-443e87b5dc30d11c2254	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0900000000-efd45bdfdb0cc42c2cb9	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-2900000000-be6e64ff24e527eb6506	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01t9-0829000000-6df80077de9156a07096	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1911000000-4ab9ec4cd0e2b2cb4feb	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0295-2900000000-78489653a0fdafbd5401	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00mk-0904000000-3dd34e382ba43fc1764f	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0arr-0596000000-829180a1d0df8715f61c	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-2900000000-e9a87fed398fa7e220c1	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-07f0-0598000000-7c06dab5e1ee09a3e269	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0j4i-1931000000-be23d1fceb38e06a6c84	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3900000000-c4aef0c58740bba64b21	2021-10-12	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cytosolic beta-glucosidase	GBA3		Q9H227	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0060077

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030731

KNApSAcK ID

Not Available

Chemspider ID

22912899

KEGG Compound ID

C05839

BioCyc ID

CPD-7417

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316113

PDB ID

Not Available

ChEBI ID

62251

References

General References

Not Available

Enzymes

Enzyme Details

1. Cytosolic beta-glucosidase

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:: GBA3
Uniprot ID:: Q9H227
Molecular weight:: Not Available

Showing Compound Card for cis-Melilotoside (CDB005057)

Structure for CDB005057 (cis-Melilotoside)

Enzymes