(9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid

Identification

Name
(9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
Accession Number
DB07302
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
42KE04U9BM
CAS number
Not Available
Weight
Average: 296.4449
Monoisotopic: 296.23514489
Chemical Formula
C18H32O3
InChI Key
NPDSHTNEKLQQIJ-UINYOVNOSA-N
InChI
InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+/t17-/m1/s1
IUPAC Name
(9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
SMILES
[H][[email protected]](O)(CCCCCCCC(O)=O)\C=C\C=C/CCCCC

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPeroxisome proliferator-activated receptor gammaNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB04670
KEGG Compound
C14767
PubChem Compound
5312830
PubChem Substance
99443773
ChemSpider
4472255
ChEBI
34496
ChEMBL
CHEMBL1230670
HET
9HO
PDB Entries
2vsr

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00322 mg/mLALOGPS
logP5.88ALOGPS
logP5.19ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity90.03 m3·mol-1ChemAxon
Polarizability37.23 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9935
Blood Brain Barrier+0.8153
Caco-2 permeable+0.7403
P-glycoprotein substrateSubstrate0.526
P-glycoprotein inhibitor INon-inhibitor0.958
P-glycoprotein inhibitor IINon-inhibitor0.7879
Renal organic cation transporterNon-inhibitor0.9265
CYP450 2C9 substrateNon-substrate0.8011
CYP450 2D6 substrateNon-substrate0.8869
CYP450 3A4 substrateNon-substrate0.6359
CYP450 1A2 substrateInhibitor0.704
CYP450 2C9 inhibitorNon-inhibitor0.9132
CYP450 2D6 inhibitorNon-inhibitor0.9424
CYP450 2C19 inhibitorNon-inhibitor0.9359
CYP450 3A4 inhibitorNon-inhibitor0.9015
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8944
Ames testNon AMES toxic0.9701
CarcinogenicityNon-carcinogens0.7204
BiodegradationReady biodegradable0.8471
Rat acute toxicity1.5862 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9332
hERG inhibition (predictor II)Non-inhibitor0.8619
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Lineolic acids and derivatives
Direct Parent
Lineolic acids and derivatives
Alternative Parents
Long-chain fatty acids / Hydroxy fatty acids / Unsaturated fatty acids / Secondary alcohols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Octadecanoid / Long-chain fatty acid / Hydroxy fatty acid / Fatty acid / Unsaturated fatty acid / Secondary alcohol / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Organic oxide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
(10E,12Z)-9-HODE (CHEBI:34496) / Other Octadecanoids (C14767) / Other Octadecanoids (LMFA02000188)

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...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
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]

Drug created on September 15, 2010 15:20 / Updated on November 09, 2017 04:09