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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:01:14 UTC
Update Date2022-03-07 02:54:01 UTC
HMDB IDHMDB0034218
Secondary Accession Numbers
  • HMDB34218
Metabolite Identification
Common NameChrysoobtusin
DescriptionChrysoobtusin 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. Chrysoobtusin has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make chrysoobtusin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Chrysoobtusin.
Structure
Data?1563862530
Synonyms
ValueSource
2-Hydroxy-1,6,7,8-tetramethoxy-3-methylanthraquinoneHMDB
Chemical FormulaC19H18O7
Average Molecular Weight358.342
Monoisotopic Molecular Weight358.10525293
IUPAC Name2-hydroxy-1,6,7,8-tetramethoxy-3-methyl-9,10-dihydroanthracene-9,10-dione
Traditional Name2-hydroxy-1,6,7,8-tetramethoxy-3-methylanthracene-9,10-dione
CAS Registry Number70588-06-6
SMILES
COC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O)=C3OC)C(=O)C2=C1
InChI Identifier
InChI=1S/C19H18O7/c1-8-6-9-12(18(25-4)14(8)20)16(22)13-10(15(9)21)7-11(23-2)17(24-3)19(13)26-5/h6-7,20H,1-5H3
InChI KeyZMDXTRSTKHTSCE-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
  • Anisole
  • Alkyl aryl ether
  • Ketone
  • Ether
  • 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
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point219 - 220 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.93 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP2.34ALOGPS
logP2.5ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)8.29ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area91.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.03 m³·mol⁻¹ChemAxon
Polarizability36.61 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]+184.28831661259
DarkChem[M-H]-184.92831661259
DeepCCS[M+H]+188.08630932474
DeepCCS[M-H]-185.72830932474
DeepCCS[M-2H]-219.40730932474
DeepCCS[M+Na]+194.63530932474
AllCCS[M+H]+181.932859911
AllCCS[M+H-H2O]+178.832859911
AllCCS[M+NH4]+184.732859911
AllCCS[M+Na]+185.532859911
AllCCS[M-H]-188.032859911
AllCCS[M+Na-2H]-187.832859911
AllCCS[M+HCOO]-187.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChrysoobtusinCOC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O)=C3OC)C(=O)C2=C14505.1Standard polar33892256
ChrysoobtusinCOC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O)=C3OC)C(=O)C2=C12885.4Standard non polar33892256
ChrysoobtusinCOC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O)=C3OC)C(=O)C2=C12999.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chrysoobtusin,1TMS,isomer #1COC1=CC2=C(C(=O)C3=C(C=C(C)C(O[Si](C)(C)C)=C3OC)C2=O)C(OC)=C1OC2921.4Semi standard non polar33892256
Chrysoobtusin,1TBDMS,isomer #1COC1=CC2=C(C(=O)C3=C(C=C(C)C(O[Si](C)(C)C(C)(C)C)=C3OC)C2=O)C(OC)=C1OC3144.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chrysoobtusin GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r7-0419000000-25a873bcf6eb159221952017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysoobtusin GC-MS (1 TMS) - 70eV, Positivesplash10-0gi3-2535900000-88686405e97d3852c6df2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysoobtusin 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 - Chrysoobtusin 10V, Positive-QTOFsplash10-0a4i-0009000000-239aeb2752a9150f3c242016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoobtusin 20V, Positive-QTOFsplash10-0a4i-0009000000-87616734e0c79cefcd732016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoobtusin 40V, Positive-QTOFsplash10-01ox-2198000000-788a4fa6de1a4ea159772016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoobtusin 10V, Negative-QTOFsplash10-0a4i-0009000000-545e3b92340f556f84352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoobtusin 20V, Negative-QTOFsplash10-0a4l-0019000000-1781f763d9f78f31c8a72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoobtusin 40V, Negative-QTOFsplash10-0cdr-0192000000-b23506a06d8305deed452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoobtusin 10V, Negative-QTOFsplash10-0a4i-0009000000-f52033267e0ba5a1ec2d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoobtusin 20V, Negative-QTOFsplash10-0a4i-0009000000-6112580b243722d3a27b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoobtusin 40V, Negative-QTOFsplash10-03di-0049000000-46c1ef05f5e59a322e452021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoobtusin 10V, Positive-QTOFsplash10-0a4i-0009000000-0bfcdd2d4921747632622021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoobtusin 20V, Positive-QTOFsplash10-0a4i-0009000000-0f98901ffd93ad3c1fec2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoobtusin 40V, Positive-QTOFsplash10-00tu-0194000000-4ea60625d40d0e0e3a932021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB012522
KNApSAcK IDC00055351
Chemspider ID136879
KEGG Compound IDC17669
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound155381
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1841271
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.. .