Showing Compound Cyanidin 3-glucoside (FDB002603)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:26 UTC

Update date

2025-11-18 22:38:38 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
Cyanidin 3-O-glucoside	ChEBI
Cyanidin 3-O-beta-D-glucoside	Kegg
Cyanidin 3-O-b-D-glucoside	Generator
Cyanidin 3-O-β-D-glucoside	Generator
Chrysontemin	HMDB
Cyanidin 3-monoglucoside	HMDB
Cyanidol 3-glucoside	HMDB
Glucocyanidin	HMDB
Kuromamine	HMDB
Cyanidin 3-O-glucopyranoside	MeSH
Cyanidin 3-O-beta-D-glucopyranoside	MeSH
2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyrylium	HMDB
2-(3,4-Dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyrylium	HMDB
3-(beta-D-Glucopyranosyloxy)-3',4',5,7-tetrahydroxyflavylium chloride	HMDB
3-(β-D-Glucopyranosyloxy)-3',4',5,7-tetrahydroxyflavylium chloride	HMDB
3-(β-D-Glucopyranosyloxy)-3’,4’,5,7-tetrahydroxyflavylium chloride	HMDB
3-O-(beta-D-Glucopyranosyl)cyanidin	HMDB
3-O-(β-D-Glucopyranosyl)cyanidin	HMDB
Asterin	HMDB
Chrysanthemin	HMDB
Chrysanthenin	HMDB
Cyanidin 3-O-beta-glucopyranoside	HMDB
Cyanidin 3-O-beta-glucoside	HMDB
Cyanidin 3-O-glucoside chloride	HMDB
Cyanidin 3-O-β-D-glucopyranoside	HMDB
Cyanidin 3-O-β-glucopyranoside	HMDB
Cyanidin 3-O-β-glucoside	HMDB
Cyanidin 3-beta-D-O-glucoside	HMDB
Cyanidin 3-beta-D-glucopyranoside	HMDB
Cyanidin 3-beta-O-glucoside	HMDB
Cyanidin 3-beta-glucopyranoside	HMDB
Cyanidin 3-beta-glucoside	HMDB
Cyanidin 3-beta-glucoside cation	HMDB
Cyanidin 3-glucoside	HMDB
Cyanidin 3-glucoside chloride	HMDB
Cyanidin 3-β-D-O-glucoside	HMDB
Cyanidin 3-β-D-glucopyranoside	HMDB
Cyanidin 3-β-O-glucoside	HMDB
Cyanidin 3-β-glucopyranoside	HMDB
Cyanidin 3-β-glucoside	HMDB
Cyanidin 3-β-glucoside cation	HMDB
Kuromanin	HMDB
Kuromanine	HMDB
Asterin?	db_source

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

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

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

Chrysanthemin

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	An agent that regulates blood sugar levels, enhancing insulin sensitivity or secretion. Therapeutically, it's used to manage diabetes, reducing symptoms and complications, and commonly prescribed to treat type 1 and 2 diabetes, as well as gestational diabetes.	DUKE
Anti hyperglycemic		An agent that lowers elevated blood glucose levels, playing a crucial biological role in regulating glucose metabolism. Therapeutically, it is used to manage hyperglycemia, with key medical applications in treating diabetes mellitus, reducing the risk of complications, and improving glycemic control.	DUKE
Anti hyperinsulinemic		An agent that lowers elevated blood insulin levels, reducing insulin resistance and hyperinsulinemia. It plays a biological role in regulating glucose metabolism and has therapeutic applications in managing type 2 diabetes, polycystic ovary syndrome (PCOS), and metabolic syndrome. Key medical uses include improving insulin sensitivity and reducing the risk of cardiovascular disease.	DUKE
Anti hyperleptinemic		An agent that reduces leptin levels in the bloodstream, regulating energy balance and metabolism. It has therapeutic applications in managing obesity, metabolic syndrome, and related disorders, and is used to treat conditions associated with high leptin levels, such as insulin resistance and type 2 diabetes.	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-obesity	52217	An agent that reduces body weight, commonly used in managing obesity and related disorders, by regulating appetite, metabolism, and fat storage, with therapeutic applications in preventing chronic diseases such as diabetes and cardiovascular disease.	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
Anti radicular		An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Cyclooxygenase-1 inhibitor	50630	An agent that blocks the activity of cyclooxygenase-1 (COX-1), reducing inflammation and pain. Therapeutically, it is used to manage conditions like arthritis, and as a nonsteroidal anti-inflammatory drug (NSAID) to relieve pain, fever, and inflammation, while minimizing gastrointestinal side effects.	DUKE
Cyclooxygenase-2 inhibitor	50629	An agent that blocks the activity of cyclooxygenase-2 (COX-2), reducing inflammation and pain. Therapeutically, it is used to manage conditions such as arthritis, menstrual cramps, and other inflammatory disorders, providing relief from symptoms with reduced gastrointestinal side effects compared to non-selective NSAIDs.	DUKE
Insulinogenic		An agent that stimulates insulin production and release by the pancreas, used therapeutically to manage diabetes and impaired glucose tolerance, and medically to treat conditions like hypoglycemia and insulin resistance.	DUKE
Larvistat		An insect growth regulator that inhibits larval development, used to control mosquito populations and prevent disease transmission, with key applications in public health and vector control.	DUKE
Lipolytic		An agent that stimulates hydrolysis of fats into fatty acids and glycerol, playing a key biological role in fat metabolism. Therapeutically, lipolytics have applications in managing obesity and hypertriglyceridemia, with medical uses including weight loss and improving lipid profiles.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	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
Secretogogue		A substance that stimulates secretion, playing a biological role in regulating hormone and enzyme release. Therapeutically, it has applications in treating conditions like hyposecretion and is used to manage digestive issues, respiratory problems, and endocrine disorders, promoting healthy secretion in various bodily systems.	DUKE