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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:20 UTC
Update Date2022-03-07 02:52:38 UTC
HMDB IDHMDB0030670
Secondary Accession Numbers
  • HMDB30670
Metabolite Identification
Common NameChrysophanol
DescriptionChrysophanol, also known as chrysophanic acid or 3-methylchrysazin, 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. Thus, chrysophanol is considered to be an aromatic polyketide. Chrysophanol 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 chrysophanol a potential biomarker for the consumption of these foods. Chrysophanol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Chrysophanol.
Structure
Data?1563862020
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 Weight254.2375
Monoisotopic Molecular Weight254.057908808
IUPAC Name1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione
Traditional Nameturkey rhubarb
CAS Registry Number481-74-3
SMILES
CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point200 - 201 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.1231661259
DarkChem[M-H]-158.731661259
DeepCCS[M+H]+159.33230932474
DeepCCS[M-H]-156.97430932474
DeepCCS[M-2H]-189.86130932474
DeepCCS[M+Na]+165.42630932474
AllCCS[M+H]+155.932859911
AllCCS[M+H-H2O]+152.032859911
AllCCS[M+NH4]+159.632859911
AllCCS[M+Na]+160.632859911
AllCCS[M-H]-158.332859911
AllCCS[M+Na-2H]-157.632859911
AllCCS[M+HCOO]-156.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChrysophanolCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O3444.5Standard polar33892256
ChrysophanolCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O2228.9Standard non polar33892256
ChrysophanolCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O2307.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chrysophanol,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C12506.8Semi standard non polar33892256
Chrysophanol,1TMS,isomer #2CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C(=O)C2=C12503.1Semi standard non polar33892256
Chrysophanol,2TMS,isomer #1CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C(=O)C2=C12566.5Semi standard non polar33892256
Chrysophanol,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C12754.9Semi standard non polar33892256
Chrysophanol,1TBDMS,isomer #2CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C(=O)C2=C12774.4Semi standard non polar33892256
Chrysophanol,2TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C(=O)C2=C13053.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fc0-0690000000-d56c5b4fdcc7de967ecf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol GC-MS (2 TMS) - 70eV, Positivesplash10-05gi-2359000000-d3bd8223a5923410d2a42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysophanol LC-ESI-QTOF , negative-QTOFsplash10-0udi-0090000000-0a16efeb6df65aacacef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysophanol LC-ESI-QTOF , negative-QTOFsplash10-0udi-0190000000-10812e976b35a4eda8622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysophanol LC-ESI-QTOF , negative-QTOFsplash10-004i-0490000000-c9aef7073169bd80cd2e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysophanol LC-ESI-QTOF , positive-QTOFsplash10-004i-0900000000-9ac1e0a42128dea2cf822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysophanol LC-ESI-QTOF , positive-QTOFsplash10-004i-0900000000-cff9163f34bb1966a8072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysophanol 20V, Negative-QTOFsplash10-0udi-0190000000-10812e976b35a4eda8622021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysophanol 40V, Negative-QTOFsplash10-004i-0490000000-c9aef7073169bd80cd2e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysophanol 10V, Negative-QTOFsplash10-0udi-0090000000-d81a22c668d9038b248b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysophanol 10V, Positive-QTOFsplash10-004i-0900000000-9ac1e0a42128dea2cf822021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chrysophanol 20V, Positive-QTOFsplash10-004i-0900000000-cff9163f34bb1966a8072021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 10V, Positive-QTOFsplash10-0a4i-0090000000-e07dfb1bc89242872bd72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 20V, Positive-QTOFsplash10-0a4i-0090000000-15cdaa0757dfee20a1cc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 40V, Positive-QTOFsplash10-0a4i-5950000000-e1a059b73e79aff8e23e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 10V, Negative-QTOFsplash10-0udi-0090000000-82cd0ac4ea31f7614f402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 20V, Negative-QTOFsplash10-0udi-0090000000-d6372d233a8f6a5cbadb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 40V, Negative-QTOFsplash10-0pbc-4970000000-8ac19f70333bd7440cef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 10V, Positive-QTOFsplash10-0a4i-0090000000-88382720cb3b98a4d4622021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 20V, Positive-QTOFsplash10-0a4i-0090000000-e08fea207b7939b57f6d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 40V, Positive-QTOFsplash10-000i-1940000000-45b0989f4038017840e82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 10V, Negative-QTOFsplash10-0udi-0090000000-ff2e7266db5d933feb852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 20V, Negative-QTOFsplash10-0udi-0090000000-ff2e7266db5d933feb852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 40V, Negative-QTOFsplash10-0h00-0590000000-c8e0292c61de829d2a422021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002584
KNApSAcK IDC00000568
Chemspider ID9793
KEGG Compound IDC10315
BioCyc IDCPD-8216
BiGG IDNot Available
Wikipedia LinkChrysophanol
METLIN IDNot Available
PubChem Compound10208
PDB IDNot Available
ChEBI ID3687
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:20877234 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .