Chrysophanic acid (CHEM017020)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:51:55 UTC
Update Date2016-11-09 01:15:30 UTC
Accession NumberCHEM017020
Identification
Common NameChrysophanic acid
ClassSmall Molecule
DescriptionA trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,8-Dihydroxy-3-methyl-9,10-anthracenedioneChEBI
1,8-Dihydroxy-3-methylanthraquinoneChEBI
3-MethylchrysazinChEBI
Chrysophanic acidChEBI
ChrysophansaeureChEBI
ChrysophanateGenerator
2-Methyl-4,5-dihydroxyanthraquinoneMeSH
3-Methyl-1,8-dihydroxyanthraquinoneMeSH
Chrysophanic acid, ion (1-)MeSH
1,8-Dihydroxy-3-methyl-9,10-anthracenedione, 9ciHMDB
1,8-Dihydroxy-3-methyl-9,10-anthraquinoneHMDB
1,8-Dihydroxy-3-methyl-anthraquinoneHMDB
1,8-Dihydroxy-3-methylanthra-9,10-quinoneHMDB
3-Methyl-1, 8-dihydroxyanthraquinoneHMDB
4, 5-Dihydroxy-2-methylanthraquinoneHMDB
4,5-Dihydroxy-2-methylanthraquinoneHMDB
9,10-Anthracenedione, 1,8-dihydroxy-3-methyl- (9ci)HMDB
ArchininHMDB
C.I. natural yellow 23HMDB
Chrysophanic acid (1,8-dihydroxy-3-methylanthraquinone)HMDB
Crysophanic acidHMDB
CrysophanolHMDB
Rheic acidHMDB
RumicinHMDB
Turkey rhubarbHMDB
Chemical FormulaC15H10O4
Average Molecular Mass254.238 g/mol
Monoisotopic Mass254.058 g/mol
CAS Registry Number481-74-3
IUPAC Name1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione
Traditional Nameturkey rhubarb
SMILESCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O
InChI IdentifierInChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3
InChI KeyLQGUBLBATBMXHT-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP3.08ALOGPS
logP4.12ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)9.14ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.15 m³·mol⁻¹ChemAxon
Polarizability25.51 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fc0-0690000000-d56c5b4fdcc7de967ecfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05gi-2359000000-d3bd8223a5923410d2a4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090000000-0a16efeb6df65aacacefSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0190000000-10812e976b35a4eda862Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0490000000-c9aef7073169bd80cd2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-9ac1e0a42128dea2cf82Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-cff9163f34bb1966a807Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-10812e976b35a4eda862Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-0490000000-c9aef7073169bd80cd2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-d81a22c668d9038b248bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-9ac1e0a42128dea2cf82Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-cff9163f34bb1966a807Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-e07dfb1bc89242872bd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-15cdaa0757dfee20a1ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5950000000-e1a059b73e79aff8e23eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-82cd0ac4ea31f7614f40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-d6372d233a8f6a5cbadbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbc-4970000000-8ac19f70333bd7440cefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-88382720cb3b98a4d462Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-e08fea207b7939b57f6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1940000000-45b0989f4038017840e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-ff2e7266db5d933feb85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-ff2e7266db5d933feb85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h00-0590000000-c8e0292c61de829d2a42Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030670
FooDB IDFDB002584
Phenol Explorer IDNot Available
KNApSAcK IDC00000568
BiGG IDNot Available
BioCyc IDCPD-8216
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkChrysophanol
Chemspider ID9793
ChEBI ID3687
PubChem Compound ID10208
Kegg Compound IDC10315
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19742131
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24136708
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24358188
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24395532
5. Kim SJ, Kim MC, Lee BJ, Park DH, Hong SH, Um JY: Anti-Inflammatory activity of chrysophanol through the suppression of NF-kappaB/caspase-1 activation in vitro and in vivo. Molecules. 2010 Sep 16;15(9):6436-51. doi: 10.3390/molecules15096436.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.