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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:28 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0003039
Secondary Accession Numbers
  • HMDB03039
Metabolite Identification
Common NameIsoacitretin
DescriptionIsoacitretin, also known as 13-cis-acitretin or soriatane, 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. Based on a literature review a significant number of articles have been published on Isoacitretin.
Structure
Thumb
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 Weight326.4293
Monoisotopic Molecular Weight326.188194698
IUPAC Name(2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Traditional Nameacetretin
CAS Registry Number69427-46-9
SMILES
COC1=C(C)C(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C/C(O)=O)C(C)=C1
InChI Identifier
InChI=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-UGOGCBOOSA-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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Epidermis
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 IDFDB023099
KNApSAcK IDNot Available
Chemspider ID4942363
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID621
PubChem Compound6437841
PDB IDNot Available
ChEBI ID50174
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMestres 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:2963014 ]
  2. Vane FM, Bugge JL, Rodriguez LC: Identification of etretinate metabolites in human blood. Drug Metab Dispos. 1989 May-Jun;17(3):280-5. [PubMed:2568909 ]
  3. 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. [PubMed:1837553 ]
  4. Vane FM, Bugge CJ, Rodriguez LC: Identification of etretinate metabolites in human bile. Drug Metab Dispos. 1989 May-Jun;17(3):275-9. [PubMed:2568908 ]
  5. 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. [PubMed:2139439 ]
  6. 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. [PubMed:1350412 ]