Retinoic acid, 13-cis- (CHEM012455)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:56:03 UTC
Update Date2016-11-09 01:14:34 UTC
Accession NumberCHEM012455
Identification
Common NameRetinoic acid, 13-cis-
ClassSmall Molecule
Description13-cis-Retinoic acid is a retinoid derivative of vitamin A used in the treatment of severe recalcitrant acne. It was most widely marketed under the brand name Accutane, which has since been discontinued. 13-cis-Retinoic acid is associated with major risks in pregnancy and so it is only available under the iPLEDGE program in the United States. The first 13-cis-Retinoic acid containing product was FDA approved on 7 May 1982.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(7E,9E,11E,13Z)-Retinoic acidChEBI
13-cis-Vitamin a acidChEBI
13-RAChEBI
AccutaneChEBI
AmnesteemChEBI
cis-RAChEBI
ClaravisChEBI
IsotretinoinaChEBI
IsotretinoineChEBI
IsotretinoinoChEBI
IsotretinoinumChEBI
Neovitamin a acidChEBI
AbsoricaKegg
SotretKegg
(7E,9E,11E,13Z)-RetinoateGenerator
13-cis-RetinoateGenerator
(13-cis)-RetinoateHMDB
(13-cis)-Retinoic acidHMDB
CIP-isotretinoinHMDB
cis-RetinoateHMDB
cis-Retinoic acidHMDB
IsotretinoinHMDB
IsotrexHMDB
RetinoateHMDB
Retinoic acidHMDB
RoaccutanHMDB
RoaccutaneHMDB
RoacutanHMDB
TeriosalHMDB
Isotretinoin zinc salt, 13 cis isomerHMDB
Isotretinoin zinc salt, 13-cis-isomerHMDB
13 cis Retinoic acidHMDB
13-cis-Retinoate,isotretinoinHMDB
13-cis-Retinoic acidChEBI
Chemical FormulaC20H28O2
Average Molecular Mass300.435 g/mol
Monoisotopic Mass300.209 g/mol
CAS Registry Number4759-48-2
IUPAC Name(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
Traditional Nameisotretinoin
SMILESC\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C\C(O)=O
InChI IdentifierInChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-
InChI KeySHGAZHPCJJPHSC-XFYACQKRSA-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
  • Diterpenoid
  • Retinoid skeleton
  • Medium-chain fatty acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Unsaturated fatty acid
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic 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 Solubility0.0048 g/LALOGPS
logP5.66ALOGPS
logP5.01ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.79 m³·mol⁻¹ChemAxon
Polarizability36.15 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-2090000000-42b8aa0666b5a088671bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-5139000000-29caedb85908ca2b99f4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0009000000-12dbd83959268dee6dbfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-066r-4900000000-31c9262cbbf0bad5b738Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fsl-9600000000-c6681587f0a9ae7a712eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uei-0494000000-28e6366fdd47e8ba2117Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-2980000000-3e7fc78de83c23830416Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-5900000000-ef4d86f8bcf86959f794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-0090000000-e07ffb4c1e5c63ab1b59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-0090000000-a0a8411213bbd2543243Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3690000000-97e6a74798dd69c30ad1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zir-0973000000-3040e9e4a1a5448efbcbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-060c-1950000000-f3b9c9b378f60b8c49a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar3-5910000000-de22eb65f274483f3f98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-0090000000-5f942e3b870e7bd0121bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0190000000-22b445382d3977280045Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-4900000000-0005b37f6d54a42a84f6Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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 IDDB00982
HMDB IDHMDB0006219
FooDB IDFDB023843
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2430432
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIsotretinoin
Chemspider ID4445539
ChEBI ID6067
PubChem Compound ID5282379
Kegg Compound IDC07058
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Blaner WS: Cellular metabolism and actions of 13-cis-retinoic acid. J Am Acad Dermatol. 2001 Nov;45(5):S129-35.
2. Chen H, Juchau MR: Recombinant human glutathione S-transferases catalyse enzymic isomerization of 13-cis-retinoic acid to all-trans-retinoic acid in vitro. Biochem J. 1998 Nov 15;336 ( Pt 1):223-6.
3. Tsukada M, Schroder M, Roos TC, Chandraratna RA, Reichert U, Merk HF, Orfanos CE, Zouboulis CC: 13-cis retinoic acid exerts its specific activity on human sebocytes through selective intracellular isomerization to all-trans retinoic acid and binding to retinoid acid receptors. J Invest Dermatol. 2000 Aug;115(2):321-7.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11606947
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11866680
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15304471
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18077132
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18788179
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19568610
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=20482692
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23676507
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=9807973