Record Information
Version1.0
Creation date2010-04-08 22:09:20 UTC
Update date2019-11-26 03:04:12 UTC
Primary IDFDB010856
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRhein
DescriptionRhein, also known as cassic acid or dipropionyl 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 lipid molecule. Rhein is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Rhein has been detected, but not quantified in, a few different foods, such as docks, garden rhubarbs, and green vegetables. This could make rhein a potential biomarker for the consumption of these foods.
CAS Number478-43-3
Structure
Thumb
Synonyms
SynonymSource
1,8-Dihydroxy-3-carboxyl anthraquinoneHMDB
1,8-Dihydroxy-3-carboxyl-9,10-anthraquinoneHMDB
1,8-Dihydroxyanthraquinone-3-carboxylic acidHMDB
4, 5-Dihydroxyanthraquinone-2-carboxylic acidHMDB
4,5-Dihydroxy-2-anthraquinonecarboxylic acidHMDB
4,5-DiOH-anthraquinone-2-COOHHMDB
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid, 9ciHMDB
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acidHMDB
Cassic acidHMDB
Chrysazin-3-carboxylic acidHMDB
Dipropionyl rheinHMDB
MonorheinHMDB
Rhein (1,8-dihydroxy-3-carboxyl anthraquinone)HMDB
Rhubarb yellowHMDB
4,5-Dihydroxyanthraquinone-2-carboxylic acidHMDB
1,8-dihydroxy-3-carboxyl anthraquinonebiospider
1,8-dihydroxy-3-carboxyl-9,10-anthraquinonebiospider
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, 9CIdb_source
9,10-dihydro-4,5-Dihydroxy-9,10-dioxo-2-anthroic acidHMDB
Rheindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP2.18ALOGPS
logP3.27ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.37 m³·mol⁻¹ChemAxon
Polarizability26.62 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H8O6
IUPAC name4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
InChI IdentifierInChI=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 KeyFCDLCPWAQCPTKC-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O
Average Molecular Weight284.2204
Monoisotopic Molecular Weight284.032087988
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthracenecarboxylic acids and derivatives
Direct ParentAnthracenecarboxylic 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 FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 63.39%; H 2.84%; O 33.77%DFC
Melting PointMp 321° (310°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data425 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07cv-0590000000-afcf37d77e69652177f2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-024r-4102900000-c5b546456fd0d7644f8aJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0090000000-9ac3e7791e49a21d3f7eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0090000000-8a0c3c4f77482fc05626JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0190000000-a217257577bda56ddeb9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0950000000-f5cac5a3a6c78fc4ed85JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0910000000-4671892dc0bcf7214bc0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-5f27d9cb7d81c2b3da8dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0190000000-87c468c6073faf9e5faeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0920000000-0b0038f124d8c1494117JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-a2294fd7666d75dbcbd0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-052u-0890000000-5f1951e9414e26b22db9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0090000000-6163d091b67836bcff63JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0190000000-bd5d0494f66cd7d5828cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rl-2290000000-33f58cc10ba47d1b818aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-05c98e64e03e092b3975JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-0090000000-ec4cf61d964a40527521JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-4390000000-5d5e000d8c2e171dd309JSpectraViewer
ChemSpider ID9762
ChEMBL IDCHEMBL418068
KEGG Compound IDC10401
Pubchem Compound ID10168
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32876
CRC / DFC (Dictionary of Food Compounds) IDFQW20-U:FQW20-U
EAFUS IDNot Available
Dr. Duke IDRHEIN
BIGG IDNot Available
KNApSAcK IDC00002861
HET IDRHN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti carcinomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cytomegalovirus22587 A substance that destroys or inhibits replication of viruses.DUKE
anti neoplastic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti plaqueDUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
candidicideDUKE
cathartic75325 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
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 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 inhibitor37670 A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).DUKE
purgative50503 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.