Showing Compound Cyanidin 3-galactoside (FDB017159)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:52 UTC

Update date

2019-11-26 03:14:19 UTC

Primary ID

FDB017159

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Cyanidin 3-galactoside

Description

Cyanidin 3-galactoside, also known as ideain or cy3-gal, 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. Thus, cyanidin 3-galactoside is considered to be a flavonoid. Cyanidin 3-galactoside is found, on average, in the highest concentration within a few different foods, such as black chokeberries (Photinia melanocarpa), lingonberries (Vaccinium vitis-idaea), and bilberries (Vaccinium myrtillus) and in a lower concentration in gooseberries (Ribes uva-crispa), apples (Malus pumila), and highbush blueberries (Vaccinium corymbosum). Cyanidin 3-galactoside has also been detected, but not quantified in, several different foods, such as sparkleberries (Vaccinium arboreum), oats (Avena sativa), carrots (Daucus carota ssp. sativus), strawberries (Fragaria X ananassa), and black tea. This could make cyanidin 3-galactoside a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cyanidin 3-galactoside.

CAS Number

27661-36-5

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Cyanidin 3-O-galactoside	ChEBI
Cyanidin 3-O-beta-D-galactoside	Kegg
Ideain	Kegg
Cyanidin 3-O-b-D-galactoside	Generator
Cyanidin 3-O-β-D-galactoside	Generator
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-chromeniumyl beta-D-galactopyranoside chloride	MeSH
Cy3-gal	MeSH
Cyanidin 3-O-beta-D-galactopyranoside	HMDB
Idaein	HMDB
Idein	HMDB
Cyanidin 3-galactoside	MeSH

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	10	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	43.04 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,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-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-WVXKDWSHSA-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

monosaccharide derivative (CHEBI:27475 )
anthocyanin cation (CHEBI:27475 )
beta-D-galactoside (CHEBI:27475 )
Anthocyanidins (C08647 )
Anthocyanidins and anthocyanins (C08647 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

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-galactoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001r-9613500000-4ecd805029dccd975fed	Spectrum
Predicted GC-MS	Cyanidin 3-galactoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-6620019000-8d5ae8efad054c2ab4aa	Spectrum
Predicted GC-MS	Cyanidin 3-galactoside, TMS_3_50, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cyanidin 3-galactoside, TMS_4_64, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cyanidin 3-galactoside, TMS_4_66, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cyanidin 3-galactoside, TMS_5_55, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cyanidin 3-galactoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cyanidin 3-galactoside, "Cyanidin 3-galactoside,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	splash10-001j-0190300000-066e4efe2ad20a1bf618	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0170-0982400000-096c82f5e6fc50eb3a1f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0090000000-a98c476e0842377a0be6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014m-0950000000-b95724097dd0841523e6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001j-0090300000-4118b3f51610a89ec6bd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0090100000-34fecd8af8ace7f092c0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0090000000-fc644549112cedb4265f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0090100000-0407b88d0009c9229fdf	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0100900000-66702edb3ac17b9bcd2f	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1300900000-733c7273cc2b516ea7fd	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ot-6910000000-5dad4cb81406b2f0a241	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-2300900000-5d1238580ea9280c8190	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-6800900000-f91084c3d800ee4ef894	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9300000000-1ee778ebb732d2be0d87	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-0061900000-b3d22fc8233274bb4ac2	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0091200000-218723bb02667d2114f5	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-009i-2091100000-e8b2df5780fffa75ac4a	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

27475

Phenol-Explorer ID

DrugBank ID

Not Available

HMDB ID

HMDB37977

CRC / DFC (Dictionary of Food Compounds) ID

ODW39-O:KWM68-J

EAFUS ID

Not Available

Dr. Duke ID

CYANIDIN-3-O-GALACTOSIDE|CYANIDIN-3-O-BETA-GALACTOSIDE|3-BETA-D-GALACTOSIDYL-CYANIDIN|CYANIDIN-3-GALACTOSIDE|IDAEIN

BIGG ID

Not Available

KNApSAcK ID

C00006652

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

Not Available

Old DFC IDS

CMQ73-Z:KWM68-J

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti capillary-fragility		An agent that strengthens capillary walls to prevent rupture, reducing bruising and bleeding. It plays a biological role in maintaining vascular integrity, and has therapeutic applications in treating conditions like purpura and hemorrhoids, with key medical uses in preventing and managing microvascular damage.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Pigment	26130	A biological coloring agent, playing a role in skin and eye protection. Therapeutically, pigments are used in photodynamic therapy and skin camouflage. Medically, they are used to treat conditions like vitiligo, albinism, and skin discoloration, as well as in diagnostic imaging and wound healing applications.	DUKE