Showing metabocard for All-trans-retinoic acid (LMDB00791)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-30 18:19:46 UTC
Update Date2018-04-30 21:15:04 UTC
LmdbLMDB00791
Secondary Accession NumbersNone
Metabolite Identification
Common NameAll-trans-retinoic acid
Descriptionall-trans-Retinoic acid, also known as all-trans-b-retinoate or agn 100335, 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. all-trans-Retinoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. all-trans-Retinoic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acidChEBI
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl)ChEBI
AGN 100335ChEBI
all-(e)-Retinoic acidChEBI
all-trans-beta-Retinoic acidChEBI
all-trans-TretinoinChEBI
all-trans-Vitamin a acidChEBI
all-trans-Vitamin a1 acidChEBI
beta-Retinoic acidChEBI
EudynaChEBI
RenovaChEBI
Retin-aChEBI
Retinoic acidChEBI
Retisol-aChEBI
Ro 1-5488ChEBI
SolageChEBI
Stieva-aChEBI
trans-Retinoic acidChEBI
Tretin mChEBI
TretinoinChEBI
VesanoidChEBI
Vitamin a acidChEBI
VitinoinChEBI
all-trans-RetinoateKegg
AvitaKegg
Retin aKegg
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoateGenerator
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate (ecl)Generator
all-(e)-RetinoateGenerator
all-trans-b-RetinoateGenerator
all-trans-b-Retinoic acidGenerator
all-trans-beta-RetinoateGenerator
all-trans-Β-retinoateGenerator
all-trans-Β-retinoic acidGenerator
b-RetinoateGenerator
b-Retinoic acidGenerator
beta-RetinoateGenerator
Β-retinoateGenerator
Β-retinoic acidGenerator
RetinoateGenerator
trans-RetinoateGenerator
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoateHMDB
Tretinoin zinc saltHMDB
trans Retinoic acidHMDB
Acid, all-trans-retinoicHMDB
Salt, tretinoin sodiumHMDB
beta all trans Retinoic acidHMDB
beta-all-trans-Retinoic acidHMDB
Acid, vitamin aHMDB
Potassium salt, tretinoinHMDB
Sodium salt, tretinoinHMDB
Acid, beta-all-trans-retinoicHMDB
Tretinoin potassium saltHMDB
Zinc salt, tretinoinHMDB
Acid, retinoicHMDB
Acid, trans-retinoicHMDB
Salt, tretinoin potassiumHMDB
Salt, tretinoin zincHMDB
Tretinoin sodium saltHMDB
all trans Retinoic acidHMDB
Retin-a microHMDB
AtralinHMDB
Tretin-XHMDB
all-trans-Retinoic acidMeSH
Chemical FormulaC20H28O2
Average Molecular Weight300.442
Monoisotopic Molecular Weight300.208930142
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
Traditional Nametretinoin
CAS Registry NumberNot Available
SMILES
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
InChI Identifier
InChI=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-YCNIQYBTSA-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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability36.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2090000000-db078f48efb8038384f2Spectrum
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
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0mc0-4941000000-401db468e6db7c5bbb5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0090000000-d05c305f987a713dfaa0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0239000000-09da873ecbe1e09a1602Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-dca272cadb8a3ba3f819Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-016r-9630000000-553ddaf9452713df67eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0390000000-241af7f979164ecfbf34Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0mc0-4941000000-05bed4117d9ed953a2caSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9400000000-3ecfeb7f6c8384d2a0d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0239000000-2c6852256fcbebe1a2aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-0910000000-a1c1aa8b35e78558cd5bSpectrum
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
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0001852
FooDB IDFDB022710
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTretinoin
Chemspider ID392618
ChEBI ID15367
PubChem Compound ID444795
Kegg Compound IDC00777
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available