Cholesteryl Linoleate

Identification

Name
Cholesteryl Linoleate
Accession Number
DB02092  (EXPT00941)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (3β)-cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoate
  • (3β)-cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoate
  • (Z,Z)-(3beta)-Cholest-5-en-3-ol 9,12-octadecadienoate
  • 18:2 Cholesteryl ester
  • CE(18:2(9Z,12Z))
  • CE(18:2)
  • cholest-5-en-3β-yl (Z,Z)-octadeca-9,12-dienoate
  • cholesteryl (9Z,12Z-octadecadienoate)
Categories
UNII
75427237HI
CAS number
604-33-1
Weight
Average: 649.0837
Monoisotopic: 648.584531676
Chemical Formula
C45H76O2
InChI Key
NAACPBBQTFFYQB-LJAITQKLSA-N
InChI
InChI=1S/C45H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/b12-11-,15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
IUPAC Name
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (9Z,12Z)-octadeca-9,12-dienoate
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@]23[H])C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ULipase 3Not AvailableYeast
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
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

References

General References
Not Available
External Links
Human Metabolome Database
HMDB00610
KEGG Compound
C15441
PubChem Compound
5287939
PubChem Substance
46505702
ChemSpider
4450205
ChEBI
41509
ZINC
ZINC000059660734
PDBe Ligand
CLL
PDB Entries
1cle

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 Solubility5.79e-06 mg/mLALOGPS
logP10.5ALOGPS
logP14.2ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity205.64 m3·mol-1ChemAxon
Polarizability86.55 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9676
Caco-2 permeable+0.7337
P-glycoprotein substrateSubstrate0.6117
P-glycoprotein inhibitor IInhibitor0.8468
P-glycoprotein inhibitor IIInhibitor0.7841
Renal organic cation transporterNon-inhibitor0.7558
CYP450 2C9 substrateNon-substrate0.8603
CYP450 2D6 substrateNon-substrate0.8939
CYP450 3A4 substrateSubstrate0.7888
CYP450 1A2 substrateNon-inhibitor0.9248
CYP450 2C9 inhibitorNon-inhibitor0.8703
CYP450 2D6 inhibitorNon-inhibitor0.9169
CYP450 2C19 inhibitorInhibitor0.7387
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5066
Ames testNon AMES toxic0.9351
CarcinogenicityNon-carcinogens0.8799
BiodegradationNot ready biodegradable0.9612
Rat acute toxicity2.0248 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8636
hERG inhibition (predictor II)Non-inhibitor0.7564
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
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0002-0000009000-be0d242fdc5dfce84520
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0002-0000009000-f746df3c4960ff441e25
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-00kb-0380309000-9563a2875a28afc28571
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
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as cholesteryl esters. These are compounds containing an esterified cholestane moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Cholesteryl esters
Alternative Parents
Cholesterols and derivatives / Delta-5-steroids / Lineolic acids and derivatives / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Cholesteryl ester / Cholesterol / Cholestane-skeleton / Delta-5-steroid / Octadecanoid / Carboxylic acid ester / Monocarboxylic acid or derivatives / Carboxylic acid derivative / Organic oxygen compound / Organic oxide
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
cholesteryl octadeca-9,12-dienoate (CHEBI:41509) / Cholesteryl esters (C15441) / Steryl esters (LMST01020008)

Targets

Kind
Protein
Organism
Yeast
Pharmacological action
Unknown
General Function
Triglyceride lipase activity
Specific Function
Not Available
Gene Name
LIP3
Uniprot ID
P32947
Uniprot Name
Lipase 3
Molecular Weight
58754.18 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on May 02, 2020 03:38

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates