Record Information
Version1.0
Creation date2010-04-08 22:11:29 UTC
Update date2019-11-26 03:10:49 UTC
Primary IDFDB014824
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhyscion
DescriptionPhyscion, also known as emodin monomethyl ether or parienin, is a member of the class of compounds known as anthraquinones. Anthraquinones are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Physcion is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Physcion can be synthesized from 2-methylanthraquinone. Physcion can also be synthesized into torososide B and physcion 8-gentiobioside. Physcion can be found in common sage, garden rhubarb, and sorrel, which makes physcion a potential biomarker for the consumption of these food products. Physcion has also been shown to protect lichens against UV-B light, at high altitudes in Alpine regions. The UV-B light stimulates production of parietin and the parietin protects the lichens from damage. Lichens in arctic regions such as Svarlbard retain this capability though they do not encounter damaging levels of UV-B, a capability that could help protect the lichens in case of Ozone layer thinning .
CAS Number521-61-9
Structure
Thumb
Synonyms
SynonymSource
1,8-Dihydroxy-3-methoxy-6-methyl-9,10-anthracenedioneChEBI
1,8-Dihydroxy-3-methoxy-6-methylanthraquinoneChEBI
1,8-Dihydroxy-3-methyl-6-methoxyanthraquinoneChEBI
Emodin monomethyl etherChEBI
ParieninChEBI
ParietinChEBI
PhyscioneChEBI
RheochrysidinChEBI
Emodin 3-methyl etherMeSH
1,8-Dihydroxy-3-methoxy-6-methyl-anthraquinonebiospider
1,8-dihydroxy-3-methoxy-6-methylanthracene-9,10-dionebiospider
1,8-Dihydroxy-3-methyl-6-methoxy-9,10-anthraquinonebiospider
9, 10-Anthracenedione, 1,8-dihydroxy-3-methoxy-6-methyl-biospider
9,10-Anthracenedione, 1,8-dihydroxy-3-methoxy-6-methyl-biospider
Anthraquinone, 1,8-dihydroxy-3-methoxy-6-methyl-biospider
Emodin-3-methyl etherbiospider
Methoxyemodinbiospider
Methylemodindb_source
Physcic aciddb_source
Physciondb_source
Physcion (senna)biospider
Przewalskinone Bdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.087 g/LALOGPS
logP2.95ALOGPS
logP3.97ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)7.89ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.62 m³·mol⁻¹ChemAxon
Polarizability28.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H12O5
IUPAC name1,8-dihydroxy-3-methoxy-6-methyl-9,10-dihydroanthracene-9,10-dione
InChI IdentifierInChI=1S/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)14-10(15(9)19)5-8(21-2)6-12(14)18/h3-6,17-18H,1-2H3
InChI KeyFFWOKTFYGVYKIR-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(C)C=C1O)C2=O
Average Molecular Weight284.2635
Monoisotopic Molecular Weight284.068473494
Classification
DescriptionThis compound belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthraquinones
Direct ParentAnthraquinones
Alternative Parents
Substituents
  • Anthraquinone
  • 9,10-anthraquinone
  • Aryl ketone
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Vinylogous acid
  • Ketone
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.60%; H 4.25%; O 28.14%DFC
Melting PointMp 209-210°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data431 (e ) (MeOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pw9-0590000000-c64a0f2564e9ff326b34JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-0995ddc6dacdafad35c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-737ec1890a5d2514f671JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6980000000-1d616b8c67c352b44e1cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-683aee905aa31a9e5ae7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-731fad27681f96ba6d82JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lxx-5890000000-5bc3d3a84be432b4f26aJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC17045
Pubchem Compound ID10639
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJJF10-F:JWL48-N
EAFUS IDNot Available
Dr. Duke IDPHYSCION
BIGG IDNot Available
KNApSAcK IDC00019420
HET IDNot Available
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 septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
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
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
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.