(5R,6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid

Identification

Generic Name
(5R,6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid
DrugBank Accession Number
DB07172
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 318.4504
Monoisotopic: 318.219494826
Chemical Formula
C20H30O3
Synonyms
Not Available

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 hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Eicosanoids
Direct Parent
Hydroxyeicosapentaenoic acids
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 / Hydroxyeicosapentaenoic acid / Long-chain 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
FTAGQROYQYQRHF-CBVHGRPESA-N
InChI
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+/t19-/m0/s1
IUPAC Name
(5R,6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid
SMILES
[H][C@@](O)(CCCC(O)=O)\C=C\C=C/C\C=C/C\C=C/C\C=C/CC

References

General References
Not Available
PubChem Compound
24875302
PubChem Substance
99443643
ChemSpider
25057526
ZINC
ZINC000008860440
PDBe Ligand
5HE
PDB Entries
2vv2

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 Solubility0.00286 mg/mLALOGPS
logP5.54ALOGPS
logP4.99Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)4.58Chemaxon
pKa (Strongest Basic)-1.5Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area57.53 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity102.59 m3·mol-1Chemaxon
Polarizability37.2 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9853
Blood Brain Barrier+0.8092
Caco-2 permeable+0.6108
P-glycoprotein substrateNon-substrate0.5401
P-glycoprotein inhibitor INon-inhibitor0.9554
P-glycoprotein inhibitor IINon-inhibitor0.8896
Renal organic cation transporterNon-inhibitor0.9397
CYP450 2C9 substrateNon-substrate0.7944
CYP450 2D6 substrateNon-substrate0.9032
CYP450 3A4 substrateNon-substrate0.651
CYP450 1A2 substrateNon-inhibitor0.649
CYP450 2C9 inhibitorNon-inhibitor0.9166
CYP450 2D6 inhibitorNon-inhibitor0.9535
CYP450 2C19 inhibitorNon-inhibitor0.9376
CYP450 3A4 inhibitorNon-inhibitor0.9219
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.891
Ames testNon AMES toxic0.9014
CarcinogenicityNon-carcinogens0.7059
BiodegradationReady biodegradable0.8394
Rat acute toxicity1.7469 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.936
hERG inhibition (predictor II)Non-inhibitor0.8937
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-5394000000-4cb164400729a114fcfc
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-4986000000-69604cae25c728063b61
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0049000000-8a7a959859565b804b86
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-066s-3393000000-a61d199eee0ee0f9043e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-3690000000-f8caa84bb82e3e8b74fe
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-8930000000-008e9156efb1c74a286f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4m-6490000000-3b2da0e50d5a785c49fa
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]-226.6362472
predicted
DarkChem Lite v0.1.0
[M-H]-178.1999
predicted
DeepCCS 1.0 (2019)
[M+H]+227.5742472
predicted
DarkChem Lite v0.1.0
[M+H]+180.5579
predicted
DeepCCS 1.0 (2019)
[M+Na]+225.8962472
predicted
DarkChem Lite v0.1.0
[M+Na]+187.10347
predicted
DeepCCS 1.0 (2019)

Targets

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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