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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:44:38 UTC
Update Date2022-03-07 02:54:58 UTC
HMDB IDHMDB0036586
Secondary Accession Numbers
  • HMDB36586
Metabolite Identification
Common Name1,3-Dimethoxyanthraquinone
Description1,3-Dimethoxyanthraquinone 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. 1,3-Dimethoxyanthraquinone has been detected, but not quantified in, several different foods, such as herbs and spices, red tea, black tea, teas (Camellia sinensis), and green tea. This could make 1,3-dimethoxyanthraquinone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,3-Dimethoxyanthraquinone.
Structure
Data?1563862893
SynonymsNot Available
Chemical FormulaC16H12O4
Average Molecular Weight268.2641
Monoisotopic Molecular Weight268.073558872
IUPAC Name1,3-dimethoxy-9,10-dihydroanthracene-9,10-dione
Traditional Name1,3-dimethoxyanthracene-9,10-dione
CAS Registry Number1989-42-0
SMILES
COC1=CC2=C(C(OC)=C1)C(=O)C1=CC=CC=C1C2=O
InChI Identifier
InChI=1S/C16H12O4/c1-19-9-7-12-14(13(8-9)20-2)16(18)11-6-4-3-5-10(11)15(12)17/h3-8H,1-2H3
InChI KeyILRJFVJXKPFIAB-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
  • Anisole
  • Alkyl aryl ether
  • Ketone
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point154 - 155 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.47 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
logP2.65ALOGPS
logP2.6ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity74.08 m³·mol⁻¹ChemAxon
Polarizability27.48 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]+161.831661259
DarkChem[M-H]-163.09231661259
DeepCCS[M+H]+161.38430932474
DeepCCS[M-H]-159.02630932474
DeepCCS[M-2H]-191.92230932474
DeepCCS[M+Na]+167.47830932474
AllCCS[M+H]+160.032859911
AllCCS[M+H-H2O]+156.232859911
AllCCS[M+NH4]+163.532859911
AllCCS[M+Na]+164.532859911
AllCCS[M-H]-164.332859911
AllCCS[M+Na-2H]-163.632859911
AllCCS[M+HCOO]-162.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,3-DimethoxyanthraquinoneCOC1=CC2=C(C(OC)=C1)C(=O)C1=CC=CC=C1C2=O3615.9Standard polar33892256
1,3-DimethoxyanthraquinoneCOC1=CC2=C(C(OC)=C1)C(=O)C1=CC=CC=C1C2=O2353.2Standard non polar33892256
1,3-DimethoxyanthraquinoneCOC1=CC2=C(C(OC)=C1)C(=O)C1=CC=CC=C1C2=O2520.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,3-Dimethoxyanthraquinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-03y3-0690000000-ed3cef34a3b3b76b4d7b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,3-Dimethoxyanthraquinone 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 - 1,3-Dimethoxyanthraquinone 10V, Positive-QTOFsplash10-014i-0090000000-078e405d1bb2710413d72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 20V, Positive-QTOFsplash10-014i-0090000000-3987c03cb2dd65eda43e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 40V, Positive-QTOFsplash10-0ka9-5290000000-47bc90fd7782874bcc272016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 10V, Negative-QTOFsplash10-014i-0090000000-b68e39f540bba3e7985a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 20V, Negative-QTOFsplash10-014i-0090000000-4a219a3b225b1c5081b52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 40V, Negative-QTOFsplash10-06ri-1190000000-84b1c6a3ebaf0b74e2272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 10V, Positive-QTOFsplash10-014i-0090000000-30b0502b3411ee2af0fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 20V, Positive-QTOFsplash10-014i-0090000000-30b0502b3411ee2af0fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 40V, Positive-QTOFsplash10-0cki-3950000000-da9b7d2f3a4ec5be54f22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 10V, Negative-QTOFsplash10-014i-0090000000-40ddcbafe3b3d64857882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 20V, Negative-QTOFsplash10-014i-0090000000-40ddcbafe3b3d64857882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 40V, Negative-QTOFsplash10-000i-0090000000-c3e0095e2330d6798b592021-09-24Wishart 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 IDFDB015498
KNApSAcK IDNot Available
Chemspider ID320911
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound361511
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1855791
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.. .