You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
Name(8R,9Z,12Z)-8-hydroxy-6-oxooctadeca-9,12-dienoic acid
Accession NumberDB07209
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 310.4284
Monoisotopic: 310.214409448
Chemical FormulaC18H30O4
InChI KeyMLHUENSFQCPBQH-ZBKJIUGYSA-N
InChI
InChI=1S/C18H30O4/c1-2-3-4-5-6-7-8-9-12-16(19)15-17(20)13-10-11-14-18(21)22/h6-7,9,12,16,19H,2-5,8,10-11,13-15H2,1H3,(H,21,22)/b7-6-,12-9-/t16-/m0/s1
IUPAC Name
(8R,9Z,12Z)-8-hydroxy-6-oxooctadeca-9,12-dienoic acid
SMILES
[H][C@@](O)(CC(=O)CCCCC(O)=O)\C=C/C\C=C/CCCCC
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Peroxisome proliferator-activated receptor gammaProteinunknownNot AvailableHumanP37231 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9652
Blood Brain Barrier+0.8683
Caco-2 permeable+0.5713
P-glycoprotein substrateSubstrate0.5535
P-glycoprotein inhibitor INon-inhibitor0.9539
P-glycoprotein inhibitor IINon-inhibitor0.747
Renal organic cation transporterNon-inhibitor0.9331
CYP450 2C9 substrateNon-substrate0.8242
CYP450 2D6 substrateNon-substrate0.8853
CYP450 3A4 substrateNon-substrate0.6294
CYP450 1A2 substrateNon-inhibitor0.5563
CYP450 2C9 inhibitorNon-inhibitor0.9229
CYP450 2D6 inhibitorNon-inhibitor0.9255
CYP450 2C19 inhibitorNon-inhibitor0.9307
CYP450 3A4 inhibitorNon-inhibitor0.7926
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9554
Ames testNon AMES toxic0.9571
CarcinogenicityNon-carcinogens0.7791
BiodegradationReady biodegradable0.8694
Rat acute toxicity1.9576 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9248
hERG inhibition (predictor II)Non-inhibitor0.9099
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0308 mg/mLALOGPS
logP4.02ALOGPS
logP4.17ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.39ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity90.52 m3·mol-1ChemAxon
Polarizability35.77 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassLineolic acids and derivatives
Sub ClassNot Available
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Keto fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation...
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular Weight:
57619.58 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Comments
comments powered by Disqus
Drug created on September 15, 2010 15:19 / Updated on August 17, 2016 12:24