Showing Compound Pelargonidin (FDB012426)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:10 UTC

Update date

2020-09-17 15:39:10 UTC

Primary ID

FDB012426

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pelargonidin

Description

Pelargonidin 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, pelargonidin is considered to be a flavonoid. Pelargonidin is found, on average, in the highest concentration within a few different foods, such as radishes (Raphanus sativus), black raspberries (Rubus occidentalis), and strawberries (Fragaria X ananassa) and in a lower concentration in elderberries (Sambucus), sour cherries (Prunus cerasus), and red raspberries (Rubus idaeus). Pelargonidin has also been detected, but not quantified in, several different foods, such as cereals and cereal products, giant butterburs (Petasites japonicus), goji, cherry tomatoes (Solanum lycopersicum var. cerasiforme), and corn salads (Valerianella locusta). This could make pelargonidin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Pelargonidin.

CAS Number

134-04-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium	ChEBI
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)benzopyrylium chloride	Kegg
3,4',5,7-Tetrahydroxyflavylium chloride	Kegg
Pelargonidin chloride	Kegg
Pelargonidol chloride	Kegg
Pelargonidine	MeSH
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride	MeSH
Pelargonidin	HMDB
Pelarogonidin	HMDB
1-Benzopyrylium, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-	biospider
3,4',5,7-Tetrahydroxy-flavylium	HMDB
3,4',5,7-Tetrahydroxyflavylium	HMDB
3,5,7-trihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium	biospider
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium(1+), 9CI	db_source
3,5,7-trihydroxy-2-(4-hydroxyphenyl)chromenylium	biospider
Pelargonidol	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	0.031 g/L	ALOGPS
logP	2.94	ALOGPS
logP	-0.5	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	6.51	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	94.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.18 m³·mol⁻¹	ChemAxon
Polarizability	27.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H11O5

IUPAC name

3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2H-chromen-2-ylium

InChI Identifier

InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-7H,(H3-,16,17,18,19)/p+1

InChI Key

XVFMGWDSJLBXDZ-UHFFFAOYSA-O

Isomeric SMILES

OC1=CC=C(C=C1)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O

Average Molecular Weight

271.2448

Monoisotopic Molecular Weight

271.060648462

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
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
1-benzopyran
Benzopyran
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:25863 )
Anthocyanidins (C05904 )
Anthocyanidins and anthocyanins (C05904 )
Anthocyanidins (LMPK12010003 )

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 66.42%; H 4.09%; O 29.49%	DFC
Melting Point	Mp 350° (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	[acid] lmax 530 (e 32000) (MeOH/HCl) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Pelargonidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-0590000000-433152a67ceebfb4760d	Spectrum
Predicted GC-MS	Pelargonidin, TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0076-3311940000-27f659d1235c6ca0641a	Spectrum
Predicted GC-MS	Pelargonidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - QTOF 6V, negative	splash10-014i-0090000000-ea3de9aeb3c6302fbfd6	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 8V, negative	splash10-014i-0190000000-e528f22236457f7bb1f9	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 10V, negative	splash10-014i-0290000000-32ea61b58eda57ea7d49	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 12V, negative	splash10-014i-0490000000-a6727c20673446687f98	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 15V, negative	splash10-014j-0790000000-56b7795234182d226541	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 2V, negative	splash10-014i-0090000000-9e3ce437f443fde49fd9	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 18V, negative	splash10-002f-0490000000-04d40c2efd76af71ca38	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 27V, positive	splash10-00xr-0190000000-c645c45f57c1bcfb43a4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-00di-0090000000-68cd52d520111f5f4bd4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 6V, positive	splash10-00di-0940000000-f04426014dc542ea58b4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 8V, positive	splash10-00di-0930000000-3bdc8c841ce0c6332685	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-00di-0910000000-a635fef1540d29a4b786	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 12V, positive	splash10-00di-0910000000-06fcbbe5e27cc9a2bf8a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-00di-0900000000-ae6ce276f7d55aa3e29d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 18V, positive	splash10-00di-0090000000-db8d9742becb27ed1c15	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-00di-0090000000-cf39a7e66f947a39bc78	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 22V, positive	splash10-00di-0090000000-e18063391fa2bcaffcd1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-00di-0190000000-8f1ff0a9e88a790097c3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-00di-0290000000-a33b9fec7b5573ee50c5	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-05c26eb7b1cc94c37edf	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0090000000-524aa4c208e3983d03d5	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0j6r-1950000000-41c9c82ef0314d300395	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-1d1e62d6b2ab0749d0a3	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-e4330de55139f36af845	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-005c-5950000000-ff425361fabac33a2ed4	2017-06-28	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

25863

Phenol-Explorer ID

DrugBank ID

Not Available

HMDB ID

HMDB03263

CRC / DFC (Dictionary of Food Compounds) ID

HGV59-L:HGV59-L

EAFUS ID

Not Available

Dr. Duke ID

PELARGONIDIN

BIGG ID

Not Available

KNApSAcK ID

C00007232

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

Pelargonidin

Phenol-Explorer Metabolite ID

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
Anti-herpetic	22587	An agent that inhibits the replication of herpes viruses, reducing symptoms and severity of infections. Therapeutically, it is used to treat herpes simplex (HSV-1 and HSV-2) and varicella-zoster virus (VZV) infections, commonly used in managing genital herpes, cold sores, and shingles.	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-viral	22587	An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.	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
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