NAV

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

Identification

Generic Name
9(S)-HODE
Commonly known or available as (9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
DrugBank Accession Number
DB07302
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 296.4449
Monoisotopic: 296.23514489
Chemical Formula
C18H32O3
Synonyms
  • (9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
  • 9S-Hode
  • alpha-Dimorphecolic acid
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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 / Hydroxy fatty acids / Unsaturated fatty acids / Secondary alcohols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Alcohol / Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Fatty acid / Hydrocarbon derivative / Hydroxy fatty acid / Long-chain fatty acid / Monocarboxylic acid or derivatives
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
(10E,12Z)-9-HODE (CHEBI:34496) / Other Octadecanoids (C14767) / Other Octadecanoids (LMFA02000188)
Affected organisms
Not Available

Chemical Identifiers

UNII
42KE04U9BM
CAS number
73543-67-6
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
CCCCC\C=C/C=C/[C@@H](O)CCCCCCCC(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0004670
KEGG Compound
C14767
PubChem Compound
5312830
PubChem Substance
99443773
ChemSpider
4472255
ChEBI
34496
ChEMBL
CHEMBL1230670
ZINC
ZINC000004655401
PDBe Ligand
9HO
PDB Entries
2vsr / 8hqn

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 Solubility0.00322 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-MSsplash10-0udi-4930000000-e1186c721ea6fb1169c7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01t9-2290000000-7710ffea9973c23faa90
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-9b848ffe645dde50d0ef
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-0490000000-65028010300d01aec6fe
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0019-7940000000-cc10b218077843ffb366
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0671-2690000000-84aa211dcdb5100a5d9a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05o1-9210000000-f225ef553650c5d0a89b
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]-205.1050301
predicted
DarkChem Lite v0.1.0
[M-H]-211.2508301
predicted
DarkChem Lite v0.1.0
[M-H]-186.71123
predicted
DeepCCS 1.0 (2019)
[M+H]+206.4893301
predicted
DarkChem Lite v0.1.0
[M+H]+210.8758301
predicted
DarkChem Lite v0.1.0
[M+H]+189.06924
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.2977301
predicted
DarkChem Lite v0.1.0
[M+Na]+211.1178301
predicted
DarkChem Lite v0.1.0
[M+Na]+195.16243
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
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 21:20 / Updated at June 12, 2020 16:52