Showing metabocard for Isoacitretin (BMDB0003039)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:02:33 UTC
Update Date2020-05-11 19:57:21 UTC
BMDB IDBMDB0003039
Secondary Accession Numbers
  • BMDB03039
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
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 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
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, Positivesplash10-03di-1279000000-d74bbc0348cfdb3b3732View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-4139000000-85e857f30a345651bb66View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-01t9-0592000000-92a48c620c961fdb430fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-1943000000-77c18bcac662a9f6bdcbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-056r-2942000000-57cdf186555912258599View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0369000000-c76928c945feff099218View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-0970000000-83c7baa1aeda7da5a2cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvi-4910000000-b657ca2b064b9ff56256View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0049000000-4a4ee208619c94b4e2c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-0079000000-35044b92edd7238b81e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-2291000000-5bb79aadc2928c46ff88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001j-0092000000-da6b1640ed88e8dd0629View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-017j-1291000000-8d03b8e6cfa817060924View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-1494000000-45aa9916567486569a90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ke9-0395000000-2d28d3c86a8a16a5adacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0940000000-2f4d9396336fd697861eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00tf-1900000000-f5a87d3a7b17af3487e6View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Epidermis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003039
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
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 ReferencesNot Available