Showing Compound Emodin (FDB013862)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:57 UTC

Update date

2019-11-26 03:09:11 UTC

Primary ID

FDB013862

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Emodin

Description

Emodin, also known as schuttgelb, belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Thus, emodin is considered to be an aromatic polyketide. Emodin has been detected, but not quantified in, a few different foods, such as docks (Rumex), garden rhubarbs (Rheum rhabarbarum), and sorrels (Rumex acetosa). This could make emodin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Emodin.

CAS Number

518-82-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione	ChEBI
1,3,8-Trihydroxy-6-methyl-9,10-anthraquinone	ChEBI
3-METHYL-1,6,8-trihydroxyanthraquinone	ChEBI
Schuttgelb	ChEBI
1,3, 8-Trihydroxy-6-methyl-9,10-anthraquinone	HMDB
1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione, 9ci	HMDB
1,3,8-Trihydroxy-6-methylanthra-9,10-quinone	HMDB
4,5,7-Trihydroxy-2-methylanthraquinone	HMDB
6-Methyl-1,3,8-trihydroxy-9,10-anthracenedione	HMDB
6-Methyl-1,3,8-trihydroxyanthraquinone	HMDB
9,10-Anthracenedione, 1,3,8-trihydroxy-6-methyl- (9ci)	HMDB
Archin	HMDB, MeSH
Emodol	HMDB
Frangula emodin	HMDB, MeSH
Frangulic acid	HMDB, MeSH
Frangulinic acid	HMDB
Rheum-emodin	HMDB
Emodin, rheum	MeSH, HMDB
Emodin, frangula	MeSH, HMDB
Rheum emodin	MeSH, HMDB
1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione, 9CI	db_source
1,3,8-trihydroxy-6-methylanthra-9,10-quinone	biospider
3-Methyl-1,6,8-trihydroxyanthraquinone	biospider
6-methyl-1,3,8-trihydroxyanthraquinone	biospider
9,10-Anthracenedione, 1,3,8-trihydroxy-6-methyl- (9CI)	biospider
Alatinone	db_source
Emodin	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.66	ALOGPS
logP	3.82	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.29	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.13 m³·mol⁻¹	ChemAxon
Polarizability	26.58 Å³	ChemAxon
Number of Rings	3	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

C15H10O5

IUPAC name

1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione

InChI Identifier

InChI=1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3

InChI Key

RHMXXJGYXNZAPX-UHFFFAOYSA-N

Isomeric SMILES

CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O

Average Molecular Weight

270.2369

Monoisotopic Molecular Weight

270.05282343

Classification

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:42223 )
Anthracenes and phenanthrenes (C10343 )
Anthraquinone type (C10343 )
Anthracenes and phenanthrenes (LMPK13040008 )

Ontology

Physiological effect

Health effect:

Health condition:

Gastrointestinal disorders:

Diarrhea

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Industrial application:

Pharmaceutical industry:

Antineoplastic agent:

Antitumor

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 66.67%; H 3.73%; O 29.60%	DFC
Melting Point	Mp 266-268° (264-265°)	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	437 (e 12600) (EtOH) (Derep)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Emodin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-007o-0590000000-e5d8430a10335839599b	Spectrum
Predicted GC-MS	Emodin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-2222900000-d6c47b3e4308e1f69c9d	Spectrum
Predicted GC-MS	Emodin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00di-0390000000-e186d58c552ffeba821e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00fr-2920000000-4cb1f49316cc48238122	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-7b75ac0aede192dc2ee6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-4df9d81040eb8a48e65c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-7b8f9b479ca718fde6ee	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0290000000-88fa3da245399884b6bc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-009e-0960000000-93c437b387d3e1aa7d90	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0090000000-79e91c5055c98d8e3db0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0090000000-bdb88728428b2b7baa22	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0090000000-9da9425656e26f3ca941	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0090000000-8c9267f9d7e631944de2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0090000000-c886ca3730f953370e44	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0190000000-41f1d89cf454e5ae7574	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-002b-0940000000-780c17885ad8db4f5a18	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0900000000-2e61cf51b55f218dea78	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0ufr-0190000000-6c97fd1b1144abdb9fed	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0umi-0190000000-fc4d25dd0d6b00a0dbc0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-05fr-1490000000-7d7df50c05fdc5d6767a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-05fr-1490000000-6dbcbd8581ffa5701094	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-cd1368af6fd71ad45899	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0090000000-2f7fb214594d9dd58ff6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-106r-2090000000-9b129a417bc060d33cc1	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-48e785e66af8396f4347	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-2524a49c780104535532	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gdi-2090000000-eb5ce4ed15fb44771926	2015-04-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

42223

Phenol-Explorer ID

Not Available

DrugBank ID

DB07715

HMDB ID

HMDB35214

CRC / DFC (Dictionary of Food Compounds) ID

JJF10-F:JJF10-F

EAFUS ID

Not Available

Dr. Duke ID

EMODIN

BIGG ID

Not Available

KNApSAcK ID

C00000555

HET ID

EMO

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Emodin

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
advanced glycation end products inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	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
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti aggregant			DUKE
anti angiogenic	48422	An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cytomegalovirus	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti feedant			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti leukemic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti lymphomic			DUKE
anti methicillin-resistant Staphylococcus aureus	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti mutagenic			DUKE
anti neoplastic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti plaque			DUKE
anti proliferant			DUKE
anti sarcomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti sprout			DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
anti vaginitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
cathartic	75325	Any substance that accelerates defecation. Compare with laxatives, which are substances that ease defecation (usually by softening faeces). A substance can be both a laxative and a cathartic.	DUKE
central nervous system depressant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
collagenase 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
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
differentiator			DUKE
estrogenic			DUKE
genotoxic	50902	A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.	DUKE
gonadotropic			DUKE
hypolipidemic			DUKE
immunostimulant	50847	A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.	DUKE
immunosuppressant	35705	An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.	DUKE
iNOS 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
leucocytogenic			DUKE
matrix-metalloproteinase-2 inhibitor	50664		DUKE
matrix-metalloproteinase-7 inhibitor	50664		DUKE
matrix-metalloproteinase-9 inhibitor	50664		DUKE
mutagenic			DUKE
nitric-oxide inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	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
prostaglandin-E2 inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
protein kinase C inhibitor	37700	An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of protein kinase C (EC 2.7.11.13).	DUKE
prostaglandin synthesis inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
protein-tyrosine-kinase 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
purgative	50503	An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.	DUKE
styptic			DUKE
topoisomerase-II inhibitor	50750	A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.	DUKE
trichomonicide			DUKE
tyrosine-kinase 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
vasodilator	35620	A drug used to cause dilation of the blood vessels.	DUKE
vasorelaxant			DUKE