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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:33:10 UTC
Update Date2019-07-23 06:14:20 UTC
HMDB IDHMDB0033790
Secondary Accession Numbers
  • HMDB33790
Metabolite Identification
Common Name1,2,8-Trihydroxy-3-methylanthraquinone
Description1,2,8-Trihydroxy-3-methylanthraquinone, also known as norobtusifolin or 2-hydroxychrysophanol, belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Thus, 1,2,8-trihydroxy-3-methylanthraquinone is considered to be an aromatic polyketide. Based on a literature review very few articles have been published on 1,2,8-Trihydroxy-3-methylanthraquinone.
Structure
Data?1563862460
Synonyms
ValueSource
NorobtusifolinChEBI
2-HydroxychrysophanolKegg
1,2,8-Trihydroxy-3-methyl-9,10-anthracenedione, 9ciHMDB
Chemical FormulaC15H10O5
Average Molecular Weight270.2369
Monoisotopic Molecular Weight270.05282343
IUPAC Name1,2,8-trihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione
Traditional Name2-hydroxychrysophanol
CAS Registry NumberNot Available
SMILES
CC1=CC2=C(C(O)=C1O)C(=O)C1=C(C=CC=C1O)C2=O
InChI Identifier
InChI=1S/C15H10O5/c1-6-5-8-11(15(20)12(6)17)14(19)10-7(13(8)18)3-2-4-9(10)16/h2-5,16-17,20H,1H3
InChI KeyCQNVSNFEXPKHGW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthraquinones
Direct ParentHydroxyanthraquinones
Alternative Parents
Substituents
  • Hydroxyanthraquinone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point265 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP10(2.71) g/LALOGPS
logP10(3.82) g/LChemAxon
logS10(-3) g/LALOGPS
pKa (Strongest Acidic)7.93ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity72.13 m³·mol⁻¹ChemAxon
Polarizability26.43 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.18531661259
DarkChem[M-H]-160.0231661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,2,8-Trihydroxy-3-methylanthraquinone,1TMS,#1CC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(O[Si](C)(C)C)=C1O2677.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,1TMS,#2CC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(O)=C1O[Si](C)(C)C2684.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,1TMS,#3CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C2=O)C(O)=C1O2693.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,2TMS,#1CC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(O[Si](C)(C)C)=C1O[Si](C)(C)C2610.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,2TMS,#2CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C2=O)C(O[Si](C)(C)C)=C1O2716.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,2TMS,#3CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C2=O)C(O)=C1O[Si](C)(C)C2739.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,3TMS,#1CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C2=O)C(O[Si](C)(C)C)=C1O[Si](C)(C)C2694.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,1TBDMS,#1CC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1O2938.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,1TBDMS,#2CC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(O)=C1O[Si](C)(C)C(C)(C)C2949.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,1TBDMS,#3CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C2=O)C(O)=C1O2954.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,2TBDMS,#1CC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C3123.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,2TBDMS,#2CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1O3228.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,2TBDMS,#3CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C2=O)C(O)=C1O[Si](C)(C)C(C)(C)C3252.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
1,2,8-Trihydroxy-3-methylanthraquinone,3TBDMS,#1CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C3388.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6y-0690000000-3b4056add4f82209afa32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone GC-MS (3 TMS) - 70eV, Positivesplash10-0229-3231900000-3581e0990d21e90aa1f22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 10V, Positive-QTOFsplash10-00di-0090000000-6c8512ee17fc07f0572c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 20V, Positive-QTOFsplash10-00di-0690000000-6934ae2059d0ab40cfc92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 40V, Positive-QTOFsplash10-0v4j-6960000000-502dd39ea62e1d644a852016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 10V, Negative-QTOFsplash10-014i-0090000000-c93b46e1ac5c7e15bd032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 20V, Negative-QTOFsplash10-014i-0090000000-1d36ebd33544f740b13f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 40V, Negative-QTOFsplash10-0gi1-3960000000-ba844b84ee063f3cb7a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 10V, Negative-QTOFsplash10-014i-0090000000-4e65ba44fc45f7e80f5a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 20V, Negative-QTOFsplash10-014i-0090000000-42a19a2704a40c8339782021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 40V, Negative-QTOFsplash10-03di-0090000000-6c8884d874b5ccbb2de12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 10V, Positive-QTOFsplash10-00di-0090000000-ae6e5e86465295cd03322021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 20V, Positive-QTOFsplash10-00di-0090000000-ae6e5e86465295cd03322021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 40V, Positive-QTOFsplash10-0udi-3970000000-b396f31bda0eff3983b92021-09-24Wishart 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 IDFDB011950
KNApSAcK IDC00002847
Chemspider ID391100
KEGG Compound IDC10379
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442759
PDB IDNot Available
ChEBI ID7635
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .