AFCDB: Ellagic acid (FDB012575)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:15 UTC

Update date

2019-11-26 03:07:07 UTC

Primary ID

FDB012575

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Ellagic acid

Description

Widely distributed in higher plants especies dicotyledons. Intestinal astringent, dietary role disputed. Nutriceutical with anticancer and antioxidation props. Ellagic acid is a Polyphenol compound found in numerous fruits and vegetables, including, raspberries; Ellagic acid is a polyphenol antioxidant found in numerous fruits and vegetables including raspberries, strawberries, cranberries, walnuts, pecans, pomegranates and other plant foods. The antiproliferative and antioxidant properties of ellagic acid have spurred preliminary research into the potential health benefits of ellagic acid consumption.; and other plant foods. It is often regarded as an antioxidant. Ellagic Acid Clinical Tests on cultured human cells also show that Ellagic acid prevents the destruction of the p53 gene by cancer cells. Additional studies suggest that one of the mechanisms by which Ellagic acid inhibits mutagenesis and carcinogenesis is by forming adducts with DNA, thus masking binding sites to be occupied by the mutagen or carcinogen.; cranberries; pecans; pomegranates; strawberries; walnuts.

CAS Number

476-66-4

Structure

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

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	1.59	ALOGPS
logP	2.32	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	5.54	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.61 m³·mol⁻¹	ChemAxon
Polarizability	26.34 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C14H6O8

IUPAC name

6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

InChI Identifier

InChI=1S/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H

InChI Key

AFSDNFLWKVMVRB-UHFFFAOYSA-N

Isomeric SMILES

OC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C(=CC(O)=C1O)C(=O)O2

Average Molecular Weight

302.194

Monoisotopic Molecular Weight

302.006267153

Classification

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Ellagic_acid
7,8-dihydroxycoumarin
Coumarin
Isocoumarin
Benzopyran
2-benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Polyol
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:4775 )
organic heterotetracyclic compound (CHEBI:4775 )
catechols (CHEBI:4775 )
polyphenol (CHEBI:4775 )
lactone (CHEBI:4775 )
Ellagitannins (C10788 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Fibroblast

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 55.64%; H 2.00%; O 42.35%	DFC
Melting Point	Mp 360°	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	366 (e 8511) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Ellagic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uk9-0095000000-fbb3052375510a43a32e	Spectrum
Predicted GC-MS	Ellagic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0100-3000090000-98c2eaf6f099a674f556	Spectrum
Predicted GC-MS	Ellagic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0009000000-40fcade2aa63aa93a2ae	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0zi0-0192000000-778eac8f3ed58bcaac74	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0zi0-0093000000-8a6cc05fc65249815e82	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0zfr-1589000000-a4f6e3a25012f7426f7d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a6r-0192000000-39923f8b1dd96716ea79	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0090000000-a1f823c8fd710f0476d9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0039000000-911cfbddb0cc618af274	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0zfr-1589000000-a4f6e3a25012f7426f7d	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-67c5a949d6d186ed40d5	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0039000000-d2f61e8b5cdaa0f142ba	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0090000000-961daa97dff240069d92	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0029000000-246b5797e3aacdc8f2f2	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0059000000-cc29f1c85d471f50bb6b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-114i-0190000000-6c3c3d5d2c468609b612	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-9600b3c9d9dcbf3cca2a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0029000000-9f6b76087b40406d9ff3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0090000000-e7359efe114a8fa3c0e3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-49d4f264ad1b5c5b0fff	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0009000000-49d4f264ad1b5c5b0fff	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6s-0090000000-6cad49e11cb1c2a2c0ee	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

417

DrugBank ID

DB08846

HMDB ID

HMDB02899

CRC / DFC (Dictionary of Food Compounds) ID

HJC14-Y:HJC14-Y

EAFUS ID

Not Available

Dr. Duke ID

ELLAGIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00011153

HET ID

REF

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

417

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
abortifacient	50691	A chemical substance that interrupts pregnancy after implantation.	DUKE
angiotensin converting enzyme inhibitor	35457	An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).	DUKE
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
anti aflatoxin	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti anaphylactic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti cariogenic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cataract	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti gingivitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti glucose-tolerance-factor			DUKE
anti HIV	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti hyperthyroid	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti malarial	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti mutagenic			DUKE
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
anti periodontic			DUKE
anti peroxidant			DUKE
anti plaque			DUKE
anti plasmodial	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti streptococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti thyroid			DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti yeast	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
apoptotic			DUKE
astringent	74783	A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
Candida-secreted-aspartyl-proteinase inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
deiodinase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
detoxicant	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
glucosyl-transferase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
hemostatic			DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
HIV-reverse-transcriptase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
juvabional			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
quinone-reductase inducer			DUKE
sunscreen	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
topoisomerase-I antagonist	50276	A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.	DUKE
xanthine oxidase inhibitor	35634	An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

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.

Ellagic acid (FDB012575)

Structure for FDB012575 (Ellagic acid)