Acitretin (CHEM016547)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:36:43 UTC
Update Date2016-11-09 01:15:25 UTC
Accession NumberCHEM016547
Identification
Common NameAcitretin
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
13-cis-AcitretinHMDB
13-cis-EtretinHMDB
SoriataneHMDB
AcitretinHMDB
Acitretin andreu brandHMDB
Acitretin roche brandHMDB
Acitretin, (Z,e,e,e)-isomerHMDB
Andreu brand OF acitretinHMDB
EtretinHMDB
Hoffmann la roche brand OF acitretinHMDB
Hoffmann-la roche brand OF acitretinHMDB
IsoetretinHMDB
NeotigasonHMDB
Roche brand OF acitretinHMDB
(2Z,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acidHMDB
IsoacitretinMeSH
Chemical FormulaC21H26O3
Average Molecular Mass326.429 g/mol
Monoisotopic Mass326.188 g/mol
CAS Registry Number55079-83-9
IUPAC Name(2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Traditional Nameacetretin
SMILESCOC1=C(C)C(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O)C(C)=C1
InChI IdentifierInChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+
InChI KeyIHUNBGSDBOWDMA-AQFIFDHZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Retinoic acid
  • Retinoid skeleton
  • Sesquiterpenoid
  • Cyclofarsesane sesquiterpenoid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Medium-chain fatty acid
  • Styrene
  • Alkyl aryl ether
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Unsaturated fatty acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.00048 g/LALOGPS
logP5.2ALOGPS
logP5.59ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)5.01ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.17 m³·mol⁻¹ChemAxon
Polarizability38.39 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1279000000-d74bbc0348cfdb3b3732Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-4139000000-85e857f30a345651bb66Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-01t9-0592000000-92a48c620c961fdb430fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-1943000000-77c18bcac662a9f6bdcbSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-2942000000-57cdf186555912258599Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0369000000-c76928c945feff099218Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-0970000000-83c7baa1aeda7da5a2cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvi-4910000000-b657ca2b064b9ff56256Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0049000000-4a4ee208619c94b4e2c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-0079000000-35044b92edd7238b81e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-2291000000-5bb79aadc2928c46ff88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001j-0092000000-da6b1640ed88e8dd0629Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-017j-1291000000-8d03b8e6cfa817060924Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-1494000000-45aa9916567486569a90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ke9-0395000000-2d28d3c86a8a16a5adacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0940000000-2f4d9396336fd697861eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00tf-1900000000-f5a87d3a7b17af3487e6Spectrum
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
DrugBank IDNot Available
HMDB IDHMDB0003039
FooDB IDFDB023099
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID621
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4942363
ChEBI ID50174
PubChem Compound ID6437841
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Mestres Quadreny, Ramon; Tortajada Lopez, Desamparados; Arrell Piquer, Maria Jose; Parra Alvarez, Margarita; Gil Grau, Salvador; Cetta Builelo, Luisa; Simo Planells, Ana. Process for the preparation of aromatic retinoic acids [e.g., etretin] and their derivatives. Span. (1992), 14 pp.
2. Al-Mallah NR, Bun H, Coassolo P, Aubert C, Cano JP: Determination of the aromatic retinoids (etretin and isoetretin) in biological fluids by high-performance liquid chromatography. J Chromatogr. 1987 Oct 9;421(1):177-86.
3. Vane FM, Bugge JL, Rodriguez LC: Identification of etretinate metabolites in human blood. Drug Metab Dispos. 1989 May-Jun;17(3):280-5.
4. Fayer BE, Huselton CA, Garland WA, Liberato DJ: Quantification of acitretin in human plasma by microbore liquid chromatography-negative chemical ionization mass spectrometry. J Chromatogr. 1991 Jul 17;568(1):135-44.
5. Vane FM, Bugge CJ, Rodriguez LC: Identification of etretinate metabolites in human bile. Drug Metab Dispos. 1989 May-Jun;17(3):275-9.
6. De Leenheer AP, Lambert WE, De Bersaques JP, Kint AH: High-performance liquid chromatographic determination of etretinate and all-trans- and 13-cis-acitretin in human plasma. J Chromatogr. 1990 Feb 2;500:637-42.
7. Larsen FG, Vahlquist C, Andersson E, Torma H, Kragballe K, Vahlquist A: Oral acitretin in psoriasis: drug and vitamin A concentrations in plasma, skin and adipose tissue. Acta Derm Venereol. 1992;72(2):84-8.