NAV

(8R,9Z,12Z)-8-hydroxy-6-oxooctadeca-9,12-dienoic acid

Identification

Generic Name
(8R,9Z,12Z)-8-hydroxy-6-oxooctadeca-9,12-dienoic acid
DrugBank Accession Number
DB07209
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 310.4284
Monoisotopic: 310.214409448
Chemical Formula
C18H30O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPeroxisome proliferator-activated receptor gammaNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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 / Keto fatty acids / Hydroxy fatty acids / Unsaturated fatty acids / Beta-hydroxy ketones / Secondary alcohols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic acyclic compound / Beta-hydroxy ketone / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Fatty acid / Hydrocarbon derivative / Hydroxy fatty acid / Keto fatty acid
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
MLHUENSFQCPBQH-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

References

General References
Not Available
PubChem Compound
46937061
PubChem Substance
99443680
ChemSpider
25059043
ZINC
ZINC000053682988
PDBe Ligand
6OC
PDB Entries
2vv4

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0308 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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00ou-3920000000-496ed719a0dae6d864a1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01tc-2690000000-833ec824c7de6a6b3f29
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-0097000000-6614b9d7eb50700ffd4f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-2981000000-847713d5bc028fdb0ef4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-7790000000-ba4bb71c4529c06896f5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ar3-9200000000-79af15e447b613c5c6f4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9860000000-3e7efff15ea4fd15756a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-173.4358
predicted
DeepCCS 1.0 (2019)
[M+H]+175.82616
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.65605
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Peroxisome proliferator-activated receptor gamma
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:19 / Updated at June 12, 2020 16:52