Record Information
Version1.0
Creation date2011-09-21 00:35:39 UTC
Update date2015-10-09 22:33:12 UTC
Primary IDFDB023843
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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
Synonyms
SynonymSource
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoateHMDB
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acidHMDB
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoateHMDB
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acidHMDB
all-(e)-RetinoateHMDB
all-(e)-Retinoic acidHMDB
all-trans-RetinoateHMDB
all-trans-TretinoinHMDB
all-trans-Vitamin a acidHMDB
all-trans-Vitamin a1 acidHMDB
beta-RetinoateHMDB
beta-Retinoic acidHMDB
RetinoateHMDB, Generator
Retinoic acidHMDB
trans-RetinoateHMDB
trans-Retinoic acidHMDB
Tretin mHMDB
Vitamin a acidHMDB
(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
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
Polarizability36.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSRetinoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052r-2090000000-042d6c8da37c5b736cfaSpectrum
Predicted GC-MSRetinoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-5149000000-4f0fac256bde7ca831e8Spectrum
Predicted GC-MSRetinoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRetinoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0292000000-d33635530f180450e1d22017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-2980000000-91b01d40cb2d53ade7882017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-6900000000-e8ee88445887714c29292017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-0090000000-7146b69cef1cebea398a2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5a-0090000000-f3edd439be98fc8297562017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053i-3590000000-16f203d5650126f7d77d2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zir-0973000000-3040e9e4a1a5448efbcb2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-060c-1950000000-f3b9c9b378f60b8c49a92021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar3-5910000000-de22eb65f274483f3f982021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-0090000000-5f942e3b870e7bd0121b2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0190000000-22b445382d39772800452021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-4900000000-0005b37f6d54a42a84f62021-10-12View Spectrum
NMRNot Available
ChemSpider ID4445539
ChEMBL IDCHEMBL547
KEGG Compound IDC07058
Pubchem Compound ID5282379
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00982
HMDB IDHMDB06219
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2430432
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference