Showing Compound Delphinidin (FDB002613)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:27 UTC

Update date

2020-02-24 19:11:07 UTC

Primary ID

FDB002613

Secondary Accession Numbers

FDB017197

Chemical Information

FooDB Name

Delphinidin

Description

Delphinidin, also known as delphinidol or ephdine, belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton. Thus, delphinidin is considered to be a flavonoid lipid molecule. Delphinidin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Delphinidin is found, on average, in the highest concentration within a few different foods, such as bilberries, cowpea, and blackcurrants and in a lower concentration in common beans, common pea, and wheats. Delphinidin has also been detected, but not quantified in, several different foods, such as brussel sprouts, fruits, horseradish tree, pepper (c. pubescens), and macadamia nuts. This could make delphinidin a potential biomarker for the consumption of these foods.

CAS Number

528-53-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3,3',4',5,5',7-Hexahydroxyflavylium	ChEBI
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)benzopyrylium chloride	Kegg
Chlorure de 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)benzopyrylium	Kegg
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)benzopyryliumchlorid	Kegg
3,3',4',5,5',7-Hexahydroxy-2-phenylbenzopyrylium chloride	Kegg
3,3',4',5,5',7-Hexahydroxyflavylium chloride	Kegg
Delfinidol chloride	Kegg
Delphinidin chloride	Kegg
Delphinidine	Kegg
Delphinidol	Kegg
Ephdine	Kegg
IdB 1056	Kegg
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-1-benzopyrylium	HMDB
Delphinidin	HMDB
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-1-benzopyrilium(1+), 9CI	db_source
Delfinidol	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	0.071 g/L	ALOGPS
logP	2.07	ALOGPS
logP	2.77	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	5.98	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	134.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.09 m³·mol⁻¹	ChemAxon
Polarizability	29.03 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H11O7

IUPAC name

3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

InChI Identifier

InChI=1S/C15H10O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-5H,(H5-,16,17,18,19,20,21)/p+1

InChI Key

JKHRCGUTYDNCLE-UHFFFAOYSA-O

Isomeric SMILES

OC1=CC2=[O+]C(=C(O)C=C2C(O)=C1)C1=CC(O)=C(O)C(O)=C1

Average Molecular Weight

303.2436

Monoisotopic Molecular Weight

303.050477706

Classification

Description

Belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Hydroxyflavonoids

Direct Parent

7-hydroxyflavonoids

Alternative Parents

Substituents

3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
1-benzopyran
Benzopyran
Pyrogallol derivative
Benzenetriol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin cation (CHEBI:28436 )
Anthocyanidins (C05908 )
Anthocyanidins (LMPK12010001 )

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 59.41%; H 3.66%; O 36.93%	DFC
Melting Point	Mp 250° (chloride)	DFC
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, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-0972000000-d3827cd3158efaa6fc24	Spectrum
Predicted GC-MS	Delphinidin, TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-4082096000-ded01bac47c04063f0e1	Spectrum
Predicted GC-MS	Delphinidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 21V, positive	splash10-0zfr-0095000000-6e45f8a95c608efdf182	2020-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT 21V, positive	splash10-0a4i-0192000000-a6ae187590233d353c26	2020-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-df99477be58e5b0ed77b	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0039000000-d472e2cb6445ef4551a4	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w4i-1942000000-bb797b6d15c7963247fe	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-042c509bd892a2c519b3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0019000000-671117d6be5a39765ce8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-5950000000-522c3856a135d6dc37d1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-a6daf5f2fb0ddb49acfd	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0049000000-a528ea784c6c42ef2afc	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgr-0290000000-66b40e51bf5b342e8b1f	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

Not Available

Phenol-Explorer ID

DrugBank ID

Not Available

HMDB ID

HMDB03074

CRC / DFC (Dictionary of Food Compounds) ID

CMR96-N:CMR96-N

EAFUS ID

Not Available

Dr. Duke ID

DELPHINIDIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

Delphinidin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Allelochemic		A chemical released by plants that interacts with other organisms, influencing their behavior or growth. Its biological role involves plant defense and communication. Therapeutically, allelochemics have anti-inflammatory, antimicrobial, and antioxidant properties, with applications in managing anxiety, pain, and infections, as well as potential anticancer uses.	DUKE
Allergenic	50904	A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.	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
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Copper chelator	38161	An agent that binds to copper, reducing its availability and activity. It plays a biological role in regulating copper levels, and has therapeutic applications in treating copper-related disorders, such as Wilson's disease and neurodegenerative diseases, by preventing copper toxicity and promoting metal homeostasis.	DUKE
Nitric-oxide inhibitor	35222	An agent that blocks the production of nitric oxide, reducing inflammation and vascular relaxation. Therapeutically, it's used to treat conditions like hypertension, angina, and septic shock, by constricting blood vessels and improving blood pressure. Key medical uses include cardiovascular and critical care applications.	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
Prooxidant		An agent that induces oxidative stress by generating reactive oxygen species (ROS) or inhibiting antioxidant systems, playing a role in cell damage and disease progression. Therapeutically, prooxidants have applications in cancer treatment, as they can selectively kill cancer cells. Key medical uses include cancer therapy and antimicrobial treatments.	DUKE