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Cholesteryl Linoleate

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Identification

Generic Name
Cholesteryl Linoleate
DrugBank Accession Number
DB02092
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 649.0837
Monoisotopic: 648.584531676
Chemical Formula
C45H76O2
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)
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Pharmacology

Indication

Not Available

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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

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
Chemical TaxonomyProvided by Classyfire
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
Aliphatic homopolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cholestane-skeleton / Cholesterol / Cholesteryl ester / Delta-5-steroid / Hydrocarbon derivative / Monocarboxylic acid or derivatives
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
cholesteryl octadeca-9,12-dienoate (CHEBI:41509) / Cholesteryl esters (C15441) / Steryl esters (LMST01020008)
Affected organisms
Not Available

Chemical Identifiers

UNII
75427237HI
CAS number
604-33-1
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
(1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-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

References

General References
Not Available
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

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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
Polarizability85.39 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-MSsplash10-02cu-2249036000-982a939d936e4145f409
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/MSsplash10-00kb-3116089000-9720617d31e8d92256d0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0020009000-cde2478cc2a4b906697d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1057029000-17d00c0a9267f9835ff5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9432013000-66def66345d5075af7d7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052s-5267298000-dfb1d9e15e33725b271f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052e-9310011000-8ef6b59715d15a3ecbfa
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-319.2424207
predicted
DarkChem Lite v0.1.0
[M-H]-309.7474207
predicted
DarkChem Lite v0.1.0
[M-H]-267.73502
predicted
DeepCCS 1.0 (2019)
[M+H]+316.9913207
predicted
DarkChem Lite v0.1.0
[M+H]+311.0424207
predicted
DarkChem Lite v0.1.0
[M+H]+269.3882
predicted
DeepCCS 1.0 (2019)
[M+Na]+317.7562207
predicted
DarkChem Lite v0.1.0
[M+Na]+309.8664207
predicted
DarkChem Lite v0.1.0
[M+Na]+275.66507
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Lipase 3
Kind
Protein
Organism
Yeast
Pharmacological action
Unknown
General Function
Not Available
Specific Function
triglyceride lipase activity
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52