AFCDB: Delphinidin 3-glucoside (FDB017191)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:56 UTC

Update date

2020-09-17 15:41:08 UTC

Primary ID

FDB017191

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Delphinidin 3-glucoside

Description

Delphinidin 3-glucoside, also known as myrtillin, belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. Delphinidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Delphinidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as bilberries, blackcurrants, and summer grapes and in a lower concentration in common beans, lowbush blueberries, and red raspberries. Delphinidin 3-glucoside has also been detected, but not quantified in, several different foods, such as eggplants, fruits, rubus (blackberry, raspberry), sweet cherries, and black chokeberries. This could make delphinidin 3-glucoside a potential biomarker for the consumption of these foods. An anthocyanin cation consisting of delphinidin having a beta-D-glucosyl residue attached at the 3-hydroxy position.

CAS Number

6906-38-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.85 g/L	ALOGPS
logP	0.93	ALOGPS
logP	0.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	213.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.24 m³·mol⁻¹	ChemAxon
Polarizability	43.8 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

C21H21O12

IUPAC name

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

InChI Identifier

InChI=1S/C21H20O12/c22-6-15-17(28)18(29)19(30)21(33-15)32-14-5-9-10(24)3-8(23)4-13(9)31-20(14)7-1-11(25)16(27)12(26)2-7/h1-5,15,17-19,21-22,28-30H,6H2,(H4-,23,24,25,26,27)/p+1/t15-,17-,18+,19-,21-/m1/s1

InChI Key

XENHPQQLDPAYIJ-PEVLUNPASA-O

Isomeric SMILES

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

Average Molecular Weight

465.3842

Monoisotopic Molecular Weight

465.103301136

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

Oligosaccharide
Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
O-glycosyl compound
Glycosyl compound
1-benzopyran
Benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxane
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

Not Available

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

Red wine

Fruits and vegetables:

Fruits:

Berries

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 54.20%; H 4.55%; O 41.25%	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	Delphinidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0feb-9602600000-45aed3fc2911f95c79eb	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-5510009000-d60ac3b75f44a32e605b	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_3_54, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_4_71, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_4_81, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_4_87, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_4_88, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_5_76, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_5_82, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_5_83, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_5_87, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_5_88, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_5_91, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_6_58, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_6_59, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_6_62, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, TMS_6_63, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-glucoside, "Delphinidin 3-glucoside,3TMS,#54" 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	splash10-0w29-0139400000-820d95dd9b931186bf3c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009100000-900e146ee03a33c5e31c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0091300000-9658b19c1d3c3ad88775	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0100900000-78712e7fc63bf2f6c41c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-1300900000-174d36b448e52a2ab4a1	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-7902100000-1c91ff38e96e02e42e96	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2300900000-0ea3c4becf795cde3fa2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-6800900000-cf4c9c44468a09663848	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9300000000-05d37d94d7cc9ad734d7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0aos-0006900000-ff93644803a0dd8e09fa	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0039400000-bcb4b7e5729a0597c0af	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k9i-5398200000-c60c5f9ebfd4dff713d0	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

10716855

ChEMBL ID

Not Available

KEGG Compound ID

C12138

Pubchem Compound ID

13915667

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

DrugBank ID

Not Available

HMDB ID

HMDB37997

CRC / DFC (Dictionary of Food Compounds) ID

OJK30-N:KWN26-A

EAFUS ID

Not Available

Dr. Duke ID

BIGG ID

Not Available

KNApSAcK ID

C00006697

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: 25244882

Old DFC IDS

CMR96-N:KWN26-A

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
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
hypoglycemic	35526	A drug which lowers the blood glucose level.	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

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

Delphinidin 3-glucoside (FDB017191)

Structure for FDB017191 (Delphinidin 3-glucoside)