Showing Compound Menthoside (FDB016372)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:24 UTC

Update date

2019-11-26 03:13:08 UTC

Primary ID

FDB016372

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Menthoside

Description

Menthoside belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Menthoside has been detected, but not quantified in, herbs and spices and peppermints (Mentha X piperita). This could make menthoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Menthoside.

CAS Number

14637-28-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
4-{5-hydroxy-4-oxo-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-2-yl}phenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator
Apigenin 7-O-rutinoside 4'-O-caffeate	HMDB
Apigenin 7-rutinoside-4'-trans-caffeate	HMDB
Menthoside	db_source

Showing 1 to 4 of 4 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	1.91	ALOGPS
logP	1.61	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	271.59 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	179.46 m³·mol⁻¹	ChemAxon
Polarizability	74.26 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C36H36O17

IUPAC name

4-{5-hydroxy-4-oxo-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-2-yl}phenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

InChI Identifier

InChI=1S/C36H36O17/c1-15-29(42)31(44)33(46)35(49-15)48-14-26-30(43)32(45)34(47)36(53-26)51-19-11-22(39)28-23(40)13-24(52-25(28)12-19)17-4-6-18(7-5-17)50-27(41)9-3-16-2-8-20(37)21(38)10-16/h2-13,15,26,29-39,42-47H,14H2,1H3/b9-3+

InChI Key

VFFCBWDFYBEZAX-YCRREMRBSA-N

Isomeric SMILES

CC1OC(OCC2OC(OC3=CC(O)=C4C(=O)C=C(OC4=C3)C3=CC=C(OC(=O)\C=C\C4=CC(O)=C(O)C=C4)C=C3)C(O)C(O)C2O)C(O)C(O)C1O

Average Molecular Weight

740.6608

Monoisotopic Molecular Weight

740.195249726

Classification

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
5-hydroxyflavonoid
Hydroxyflavonoid
Flavone
Phenolic glycoside
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Disaccharide
Glycosyl compound
O-glycosyl compound
Chromone
Benzopyran
Phenol ester
1-benzopyran
Styrene
Catechol
Phenoxy compound
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Pyranone
Pyran
Oxane
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Enoate ester
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

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 58.38%; H 4.90%; O 36.72%	DFC
Melting Point	Mp 271-273°	DFC
Optical Rotation	[a]18D -89 (c, 0.1 in DMF)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Menthoside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Menthoside, TMS_2_16, 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	splash10-01x0-0500940700-5bd9390a6f3cab716c5c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02ai-0620920000-55c4c228b405bb65162f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-097i-1950600000-d00471ce67dede53f54f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01q0-3611850900-2beacb44ba86d5829d93	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-3910820200-b51862e8f157962100d1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03e9-4763900000-100686db993eb99e0232	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001l-0000900400-43cc45a936d286ada093	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001k-0000990100-58f9f169e3b1c8beee8c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0000900000-18feaf40eb6b2fbcb077	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000010900-049915d994380c78e006	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001c-0000570900-1947d2ccdf068114884e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0000900100-0d71e40e54ac117b7172	2021-09-22	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

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB37350

CRC / DFC (Dictionary of Food Compounds) ID

KQW27-E:KQW49-M

EAFUS ID

Not Available

Dr. Duke ID

MENTHOSIDE

BIGG ID

Not Available

KNApSAcK ID

C00004193

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

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound Menthoside (FDB016372)

Structure for FDB016372 (Menthoside)