AFCDB: Cyanidin 3-glucoside (FDB002603)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:26 UTC

Update date

2020-09-17 15:41:08 UTC

Primary ID

FDB002603

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Cyanidin 3-glucoside

Description

Cyanidin 3-glucoside, also known as asterin? or chrysontemin, belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Cyanidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cyanidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as black elderberries, rubus (blackberry, raspberry), and bilberries and in a lower concentration in redcurrants, strawberries, and sweet oranges. Cyanidin 3-glucoside has also been detected, but not quantified in, several different foods, such as common pea, peachs, tartary buckwheats, soft-necked garlics, and fats and oils. This could make cyanidin 3-glucoside a potential biomarker for the consumption of these foods. An anthocyanin cation that is a cyanidin cation linked to a beta-D-glucosyl moiety at position 3.

CAS Number

7084-24-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.6 g/L	ALOGPS
logP	0.98	ALOGPS
logP	0.39	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	6.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	193.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.26 m³·mol⁻¹	ChemAxon
Polarizability	43.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H21O11

IUPAC name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

InChI Identifier

InChI=1S/C21H20O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26)/p+1/t16-,17-,18+,19-,21-/m1/s1

InChI Key

RKWHWFONKJEUEF-GQUPQBGVSA-O

Isomeric SMILES

OC[C@H]1O[C@@H](OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

Average Molecular Weight

449.3848

Monoisotopic Molecular Weight

449.108386514

Classification

Description

Belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-3-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
Anthocyanidin
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:28426 )
monosaccharide derivative (CHEBI:28426 )
anthocyanin cation (CHEBI:28426 )
Anthocyanidins (C08604 )
Anthocyanidins and anthocyanins (C08604 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biofluid and excreta:

Urine

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Red wine

Fruits and vegetables:

Fruits:

Berries

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 56.13%; H 4.71%; O 39.16%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Cyanidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001r-9613500000-4ecd805029dccd975fed	Spectrum
Predicted GC-MS	Cyanidin 3-glucoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-6620019000-8d5ae8efad054c2ab4aa	Spectrum
Predicted GC-MS	Cyanidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cyanidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cyanidin 3-glucoside, TMS_3_50, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cyanidin 3-glucoside, TMS_4_64, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cyanidin 3-glucoside, TMS_4_66, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cyanidin 3-glucoside, TMS_5_55, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cyanidin 3-glucoside, "Cyanidin 3-glucoside,3TMS,#50" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0012-0190300000-fa49c39b10bc818caf38	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0170-0982400000-bf6abe51e9ef29f65fe0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001r-0190000000-1d3575fd8a5bad57646c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0940000000-688e280b84a3b096281c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001s-0090200000-abde441c456e0554b97b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0090100000-d8c555166d10dec1fb48	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0090000000-0ee5168148d1f43f98b9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0090100000-1dc5f0ee658f46d936df	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 31V, positive	splash10-000i-0090000000-62b9d786642d93613772	2020-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT 31V, positive	splash10-000i-0090000000-503a1596bd2451e838d7	2020-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090200000-d45f62202546a09960c4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0190000000-86b08922db000308f1b5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-0890000000-f54a34d80fd4bb859a26	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-0061900000-b3d22fc8233274bb4ac2	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0091200000-218723bb02667d2114f5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-009i-2091100000-e8b2df5780fffa75ac4a	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

3679222

ChEMBL ID

Not Available

KEGG Compound ID

C08604

Pubchem Compound ID

4481259

Pubchem Substance ID

Not Available

ChEBI ID

28426

Phenol-Explorer ID

DrugBank ID

Not Available

HMDB ID

HMDB30684

CRC / DFC (Dictionary of Food Compounds) ID

ODW39-O:CMQ75-B

EAFUS ID

Not Available

Dr. Duke ID

CYANIDIN-3-O-GLUCOSIDE|CYANIDIN-3-O-BETA-D-GLUCOSIDE|CYANIDIN-3-MONOGLUCOSIDE|CYANIDIN-3-GLUCOSIDE|CHRYSANTHEMIN

BIGG ID

Not Available

KNApSAcK ID

C00002374

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

Duplicate IDS

Pubchem compound: 25244576

Old DFC IDS

CMQ73-Z:CMQ75-B

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hyperglycemic			DUKE
anti hyperinsulinemic			DUKE
anti hyperleptinemic			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti obesity	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti radicular			DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cyclooxygenase-1 inhibitor	50630	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.	DUKE
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	DUKE
insulinogenic			DUKE
larvistat			DUKE
lipolytic			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
pigment	26130	An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.	DUKE
secretogogue			DUKE

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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.

Cyanidin 3-glucoside (FDB002603)

Structure for FDB002603 (Cyanidin 3-glucoside)