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13-cis-Retinoic acid (PC000880)

Record Information
Version1.0
Creation date2015-10-09 22:33:11 UTC
Update date2017-01-19 02:36:40 UTC
FoodComEx IDPC000880
FoodDB RecordFDB023843
Chemical Information
Name13-cis-Retinoic acid
DescriptionA topical dermatologic agent that is used in the treatment of acne vulgaris and several other skin diseases. The drug has teratogenic and other adverse effects. (PubChem) 13-cis-retinoic acid is also a naturally occurring retinoid that is present in the circulation. Although 13-cis-retinoic acid (isotretinoin) does not have the potent gene regulatory activity of other isomers, it is an effective pharmacologic agent for treating a variety of dermatologic conditions. (PMID: 11606944) The steric conversion of 13-cis-retinoic acid (13-cRA) to all-trans-retinoic acid (t-RA) has been proposed as an activation mechanism for the observed therapeutic and teratogenic activities of 13-cRA. (PMID: 9806904) 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. (PMID: 10951254) [HMDB]
CAS Number4759-48-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(13-cis)-RetinoateHMDB
(13-cis)-Retinoic acidHMDB
(13cis)-Retinoatehmdb
(13cis)-Retinoic acidhmdb
(7e,9e,11e,13Z)-RetinoateGenerator
(7e,9e,11e,13Z)-Retinoic acidChEBI
13-cis-Vitamin A acidhmdb
13-RAChEBI
Accutanehmdb
Accutane (TN)hmdb
Amnesteemhmdb
CIP-Isotretinoinhmdb
cis-RAChEBI
cis-Retinoatehmdb
cis-Retinoic acidhmdb
Claravishmdb
Isotretinoinhmdb
Isotretinoin (USP)hmdb
Isotretinoin [USAN:BAN:INN]hmdb
IsotretinoinaChEBI
IsotretinoineChEBI
Isotretinoine [INN-French]hmdb
IsotretinoinoChEBI
Isotretinoino [INN-Spanish]hmdb
IsotretinoinumChEBI
Isotretinoinum [INN-Latin]hmdb
Isotrexhmdb
Neovitamin A acidhmdb
Roaccutanhmdb
Roaccutanehmdb
Roacutanhmdb
Sotrethmdb
Teriosalhmdb
Chemical FormulaC20H28O2
IUPAC name3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
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)
InChI KeySHGAZHPCJJPHSC-UHFFFAOYSA-N
Isomeric SMILESCC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(O)=O
Average Molecular Weight300.4351
Monoisotopic Molecular Weight300.20893014
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 10 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci 0009TG
AKSci F739
AKSci J10790
Toronto Research Chemicals R250000