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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:24 UTC
Update Date2018-03-12 22:10:53 UTC
HMDB IDHMDB0029752
Secondary Accession Numbers
  • HMDB29752
Metabolite Identification
Common NameDantron
DescriptionDantron, also known as chrysazin or dorbane, 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. Dantron exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, dantron is primarily located in the membrane (predicted from logP). Dantron can be converted into aloe emodin and chrysophanol. Outside of the human body, dantron can be found in green vegetables. This makes dantron a potential biomarker for the consumption of this food product.
Structure
Thumb
Synonyms
ValueSource
1,8-Dihydroxy-9,10-anthracenedioneChEBI
1,8-Dihydroxy-9,10-anthraquinoneChEBI
1,8-Dihydroxyanthra-9,10-quinoneChEBI
1,8-DihydroxyanthrachinonChEBI
1,8-DihydroxyanthraquinoneChEBI
DanthronChEBI
DantronaChEBI
DantroneChEBI
DantronumChEBI
DioxyanthrachinonumChEBI
1,8-DihydroanthraquinoneHMDB
1,8-Dihydroxy-9,10-anthracenedione, 9ciHMDB
1,8-Dihydroxyanthracene-9,10-dioneHMDB
1,8-DioxyanthraquinoneHMDB
AltanHMDB
AntrapurolHMDB
ChrysazinHMDB
ChrysazineHMDB
CriasazinHMDB
Danthron, banHMDB
DanthroneHMDB
Dantron, innHMDB
DiaquoneHMDB
DorbaneHMDB
IstizinHMDB
LaxanormHMDB
LaxanthreenHMDB
LaxipurHMDB
LaxipurinHMDB
ZwitsalaxHMDB
DuolaxMeSH
DanthaneMeSH
DorbanexMeSH
Chemical FormulaC14H8O4
Average Molecular Weight240.2109
Monoisotopic Molecular Weight240.042258744
IUPAC Name1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione
Traditional Namealtan
CAS Registry Number117-10-2
SMILES
OC1=CC=CC2=C1C(=O)C1=C(C=CC=C1O)C2=O
InChI Identifier
InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H
InChI KeyQBPFLULOKWLNNW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point193 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP2.98ALOGPS
logP3.61ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.11 m³·mol⁻¹ChemAxon
Polarizability23.19 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-1690000000-e493908abfb426f6216dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-7629000000-370e0237e8f70fd7cfbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-f33bba4b2a76f616e555View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-debf61aa41c5f09488ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-0b90944c9e69d24702c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03dr-0290000000-b75bbfaef6b643f8b203View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03e9-0960000000-51a32afa2b48f66fdc1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-62d161034c5eb4b42e8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-0b7c1878d26055d6badcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-4290000000-9c7d7350a61a78487046View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-968889b6ae63480b6a0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-968889b6ae63480b6a0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3190000000-b113fe59304580347faaView in MoNA
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 IDDB04816
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000955
KNApSAcK IDC00002804
Chemspider ID2845
KEGG Compound IDC10312
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDantron
METLIN IDNot Available
PubChem Compound2950
PDB IDCHZ
ChEBI ID3682
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.. .

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Mikhailova ON, Filipenko ML, Timofeeva OA, Kaledin VI, Guliaeva LF, Liakhovich VV: [mRNA level and cytochrome P450 1A activity in the liver of C57BL mice induced by various xenobiotics]. Biomed Khim. 2003 Jul-Aug;49(4):388-93. [PubMed:14562683 ]