Showing Compound Rhein (FDB010856)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:20 UTC

Update date

2019-11-26 03:04:12 UTC

Primary ID

FDB010856

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Rhein

Description

Rhein belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. Thus, rhein is considered to be an aromatic polyketide. Rhein has been detected, but not quantified in, a few different foods, such as docks (Rumex), garden rhubarbs (Rheum rhabarbarum), and green vegetables. This could make rhein a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Rhein.

CAS Number

478-43-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,8-Dihydroxy-3-carboxyl anthraquinone	HMDB
1,8-Dihydroxy-3-carboxyl-9,10-anthraquinone	HMDB, MeSH
1,8-Dihydroxyanthraquinone-3-carboxylic acid	HMDB
4, 5-Dihydroxyanthraquinone-2-carboxylic acid	HMDB
4,5-Dihydroxy-2-anthraquinonecarboxylic acid	HMDB
4,5-DiOH-anthraquinone-2-COOH	HMDB
9,10-dihydro-4,5-Dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid, 9ci	HMDB
9,10-dihydro-4,5-Dihydroxy-9,10-dioxo-2-anthroic acid	HMDB
Cassic acid	HMDB
Chrysazin-3-carboxylic acid	HMDB
Dipropionyl rhein	HMDB, MeSH
Monorhein	HMDB
Rhein (1,8-dihydroxy-3-carboxyl anthraquinone)	HMDB
Rhubarb yellow	HMDB
4,5-Dihydroxyanthraquinone-2-carboxylic acid	MeSH, HMDB
1,8-dihydroxy-3-carboxyl anthraquinone	biospider
1,8-dihydroxy-3-carboxyl-9,10-anthraquinone	biospider
2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9, 10-dioxo-	biospider
2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-	biospider
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid, 9CI	db_source
Rhein	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	2.18	ALOGPS
logP	3.27	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.37 m³·mol⁻¹	ChemAxon
Polarizability	26.62 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

C15H8O6

IUPAC name

4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

InChI Identifier

InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)

InChI Key

FCDLCPWAQCPTKC-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O

Average Molecular Weight

284.2204

Monoisotopic Molecular Weight

284.032087988

Classification

Description

Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
9,10-anthraquinone
Anthraquinone
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Hydroxybenzoic acid
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

anthracenes (CHEBI:8825 )
Anthracenes and phenanthrenes (C10401 )
Anthraquinone type (C10401 )
Anthracenes and phenanthrenes (LMPK13040015 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Household products:

Antimicrobial agent

Pharmaceutical industry:

Pharmaceutical

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 63.39%; H 2.84%; O 33.77%	DFC
Melting Point	Mp 321° (310°)	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	425 () (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Rhein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-07cv-0590000000-afcf37d77e69652177f2	Spectrum
Predicted GC-MS	Rhein, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-024r-4102900000-c5b546456fd0d7644f8a	Spectrum
Predicted GC-MS	Rhein, 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-QQ , negative	splash10-001i-0090000000-9ac3e7791e49a21d3f7e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0090000000-8a0c3c4f77482fc05626	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0190000000-a217257577bda56ddeb9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0950000000-f5cac5a3a6c78fc4ed85	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0910000000-4671892dc0bcf7214bc0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-0090000000-5f27d9cb7d81c2b3da8d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-0190000000-87c468c6073faf9e5fae	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0920000000-0b0038f124d8c1494117	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0090000000-a2294fd7666d75dbcbd0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-052u-0890000000-5f1951e9414e26b22db9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0920000000-5757933ef5a7532b4ef1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-a2294fd7666d75dbcbd0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000l-0090000000-a2178fdd7c56081cab09	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-8f070d596b12739e117e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0ac0-0910000000-a9cb6e465076d6963a82	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-2c3cbe9c71ab4af87a66	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0290000000-66c888a0ecf96ae01c8c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0920000000-eb6d2ee2a66f5ba2d590	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-467e222d330c2d39d5b1	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0090000000-6163d091b67836bcff63	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0190000000-bd5d0494f66cd7d5828c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00rl-2290000000-33f58cc10ba47d1b818a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-05c98e64e03e092b3975	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0019-0090000000-ec4cf61d964a40527521	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ku-4390000000-5d5e000d8c2e171dd309	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

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB32876

CRC / DFC (Dictionary of Food Compounds) ID

FQW20-U:FQW20-U

EAFUS ID

Not Available

Dr. Duke ID

RHEIN

BIGG ID

Not Available

KNApSAcK ID

C00002861

HET ID

RHN

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

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
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti carcinomic	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 cytomegalovirus	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti neoplastic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti plaque			DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	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
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
candidicide			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
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	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
proteinase inhibitor	37670	A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).	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