Showing Compound cis-p-Coumaric acid 4-glucoside (FDB021351)

Record Information

Version

1.0

Creation date

2010-04-08 22:15:38 UTC

Update date

2019-11-26 03:20:16 UTC

Primary ID

FDB021351

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

cis-p-Coumaric acid 4-glucoside

Description

Trans-p-coumaric acid 4-glucoside, also known as 4-O-beta-D-glucosyl-4-coumaric acid or 4-O-beta-D-glucosyl-4-hydroxycinnamate, is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides 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. Trans-p-coumaric acid 4-glucoside is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Trans-p-coumaric acid 4-glucoside can be found in loquat, which makes trans-p-coumaric acid 4-glucoside a potential biomarker for the consumption of this food product.

CAS Number

117405-48-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2E)-3-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate	Generator
(Z)-3-(4-Hydroxyphenyl)-2-propenoic acid 4-O-b-D-glucopyranoside	manual
(Z)-3-(4-Hydroxyphenyl)-2-propenoic acid O-b-D-glucopyranoside	manual
3-(4-(beta-D-Glucopyranosyloxy)phenyl)-2-propenoic acid	HMDB
3-[4-(beta-D-Glucopyranosyloxy)phenyl]acrylic acid	HMDB
3-[4-(beta-D-Glucopyranosyloxy)phenyl]prop-2-enoic acid	HMDB
4-O-[4-(2-Carboxyvinyl)phenyl]-beta-D-glucopyranose	HMDB
4-O-beta-D-Glucosyl-4-coumaric acid	HMDB
4-O-beta-D-Glucosyl-4-hydroxycinnamate	HMDB
4-O-beta-Glucopyranosyl-cis-p-coumaric acid	biospider

Showing 1 to 10 of 15 entries

Predicted Properties

Property	Value	Source
Water Solubility	5.08 g/L	ALOGPS
logP	-0.35	ALOGPS
logP	-0.44	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.72	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	31.85 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

Chemical Formula

C15H18O8

IUPAC name

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

InChI Identifier

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

InChI Key

LJFYQZQUAULRDF-ZZXKWVIFSA-N

Isomeric SMILES

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

Average Molecular Weight

326.2986

Monoisotopic Molecular Weight

326.100167552

Classification

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 55.21%; H 5.56%; O 39.23%	DFC
Melting Point	Mp 133-140°	DFC
Optical Rotation	[a]25D -60 (c, 0.2 in MeOH)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	xi-p-Coumaric acid 4-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0zfr-5943000000-c492ad4cea7748c10d1d	Spectrum
Predicted GC-MS	xi-p-Coumaric acid 4-glucoside, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-1020229000-cd5e122c29a7c414bbb3	Spectrum
Predicted GC-MS	xi-p-Coumaric acid 4-glucoside, 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	splash10-0691-0935000000-c974f539415af8bc2656	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0910000000-2b9e08298c82be733463	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kb-1900000000-301e2a0a8e986454b07e	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01t9-1928000000-664ca3f5aa531f156b9f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1911000000-33266a1715378857682a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03xs-3900000000-6a847d57baead9a24cf2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00or-0906000000-ff40c38471b820f5cd46	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02t9-2920000000-9836ca930b3e9ff1b7ef	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-8cc86ba16bb3961ac899	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0906000000-b01d52f59a8d17a35095	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0694000000-5fd94da869aa357b76dc	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-2910000000-f71f5d773ce8ae94144e	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

36090

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CMP73-U:NRL77-E

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00031477

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound cis-p-Coumaric acid 4-glucoside (FDB021351)

Structure for FDB021351 (cis-p-Coumaric acid 4-glucoside)