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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 01:47:31 UTC
Update Date2021-09-26 22:58:46 UTC
HMDB IDHMDB0248463
Secondary Accession NumbersNone
Metabolite Identification
Common Nameanthralin
Descriptionanthralin, also known as dithranol or anthraderm, belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. Based on a literature review a significant number of articles have been published on anthralin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Anthralin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically anthralin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
1,8-Dihydroxy-9(10H)-anthracenoneChEBI
1,8-Dihydroxy-9-anthroneChEBI
1,8-DihydroxyanthroneChEBI
DithranolChEBI
AnthradermKegg
1,8 Dihydroxy 9 anthroneHMDB
1,8,9-AnthracenetriolHMDB
AnthraforteHMDB
AnthranolHMDB
CignolinHMDB
CygnolineHMDB
DihydroxyanthranolHMDB
DithrocreamHMDB
Ditranol fnaHMDB
FNA, ditranolHMDB
LasanHMDB
MicanolHMDB
PsoradrateHMDB
PsoricrèmeHMDB
Chemical FormulaC14H10O3
Average Molecular Weight226.231
Monoisotopic Molecular Weight226.062994182
IUPAC Name1,8-dihydroxy-9,10-dihydroanthracen-9-one
Traditional Nameanthralin
CAS Registry NumberNot Available
SMILES
OC1=CC=CC2=C1C(=O)C1=C(O)C=CC=C1C2
InChI Identifier
InChI=1S/C14H10O3/c15-10-5-1-3-8-7-9-4-2-6-11(16)13(9)14(17)12(8)10/h1-6,15-16H,7H2
InChI KeyNUZWLKWWNNJHPT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassNot Available
Direct ParentAnthracenes
Alternative Parents
Substituents
  • Anthracene
  • 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
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.73ALOGPS
logP4.24ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)8.47ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity64.27 m³·mol⁻¹ChemAxon
Polarizability23.12 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
DeepCCS[M+H]+149.84130932474
DeepCCS[M-H]-147.44530932474
DeepCCS[M-2H]-180.83730932474
DeepCCS[M+Na]+155.82930932474
AllCCS[M+H]+149.532859911
AllCCS[M+H-H2O]+145.432859911
AllCCS[M+NH4]+153.432859911
AllCCS[M+Na]+154.532859911
AllCCS[M-H]-151.032859911
AllCCS[M+Na-2H]-150.332859911
AllCCS[M+HCOO]-149.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
anthralinOC1=CC=CC2=C1C(=O)C1=C(O)C=CC=C1C23356.4Standard polar33892256
anthralinOC1=CC=CC2=C1C(=O)C1=C(O)C=CC=C1C22111.1Standard non polar33892256
anthralinOC1=CC=CC2=C1C(=O)C1=C(O)C=CC=C1C22099.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - anthralin GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-1970000000-42a9d9751f6487d3d8562021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - anthralin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - anthralin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - anthralin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - anthralin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - anthralin GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-3790000000-74ab4aae2d6ceb3138312014-10-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anthralin 10V, Positive-QTOFsplash10-004i-0090000000-206fa731ad283ac4a48e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anthralin 20V, Positive-QTOFsplash10-004i-0090000000-b9d606e04eaa7d9016b82016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anthralin 40V, Positive-QTOFsplash10-004l-4390000000-b1ed4530ad723f85a5d92016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anthralin 10V, Negative-QTOFsplash10-004i-0090000000-bd8e406914579439bd8c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anthralin 20V, Negative-QTOFsplash10-004i-0090000000-bd8e406914579439bd8c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anthralin 40V, Negative-QTOFsplash10-004i-4290000000-bace3a8a42b786d416c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anthralin 10V, Positive-QTOFsplash10-004i-0090000000-1158eb6b952d47f228592021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anthralin 20V, Positive-QTOFsplash10-004i-0290000000-b694bbd0d67d3d4327fe2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anthralin 40V, Positive-QTOFsplash10-0002-2900000000-ae5612a3d12e059890c42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anthralin 10V, Negative-QTOFsplash10-004i-0090000000-6929adb4eb50cc47a2972021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anthralin 20V, Negative-QTOFsplash10-004i-0090000000-6929adb4eb50cc47a2972021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anthralin 40V, Negative-QTOFsplash10-002b-0960000000-b81b31e521f1ef5cdd852021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11157
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2117
KEGG Compound IDC06831
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDithranol
METLIN IDNot Available
PubChem Compound2202
PDB IDNot Available
ChEBI ID37510
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]