Dithranol (CHEM016095)

Record Information
Version1.0
Creation Date2016-05-20 16:14:22 UTC
Update Date2026-05-14 19:07:28 UTC
Accession NumberCHEM016095
Identification
Common NameDithranol
ClassSmall Molecule
Description
An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9.
Contaminant Sources
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
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 Mass226.231 g/mol
Monoisotopic Mass226.063 g/mol
CAS Registry Number1143-38-0
IUPAC Name1,8-dihydroxy-9,10-dihydroanthracen-9-one
Traditional Nameanthralin
SMILESOC1=CC=CC2=C1C(=O)C1=C(O)C=CC=C1C2
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
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
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB11157
HMDB IDHMDB0248463
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDithranol
Chemspider ID2117
ChEBI ID37510
PubChem Compound ID2202
Kegg Compound IDC06831
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1640019
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22335232
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22370944
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22931516
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23079823
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23088318
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23488784
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23594093
9. 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.