N-3-OXO-DODECANOYL-L-HOMOSERINE LACTONE

Identification

Name
N-3-OXO-DODECANOYL-L-HOMOSERINE LACTONE
Accession Number
DB08324
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 297.3899
Monoisotopic: 297.194008357
Chemical Formula
C16H27NO4
InChI Key
PHSRRHGYXQCRPU-AWEZNQCLSA-N
InChI
InChI=1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1
IUPAC Name
3-oxo-N-[(3S)-2-oxooxolan-3-yl]dodecanamide
SMILES
[H][[email protected]@]1(CCOC1=O)NC(=O)CC(=O)CCCCCCCCC

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTranscriptional activator protein LasRNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
3246941
PubChem Substance
99444795
ChemSpider
2497481
BindingDB
50351512
ChEBI
44534
ChEMBL
CHEMBL8483
HET
OHN
PDB Entries
2uv0 / 3ix3 / 3szt / 4ng2

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 Solubility0.0475 mg/mLALOGPS
logP2.9ALOGPS
logP2.95ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)10.31ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.47 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity79.59 m3·mol-1ChemAxon
Polarizability34.12 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.984
Blood Brain Barrier+0.8141
Caco-2 permeable-0.5899
P-glycoprotein substrateNon-substrate0.6643
P-glycoprotein inhibitor INon-inhibitor0.6453
P-glycoprotein inhibitor IINon-inhibitor0.7288
Renal organic cation transporterNon-inhibitor0.875
CYP450 2C9 substrateNon-substrate0.765
CYP450 2D6 substrateNon-substrate0.8237
CYP450 3A4 substrateSubstrate0.5431
CYP450 1A2 substrateNon-inhibitor0.8258
CYP450 2C9 inhibitorNon-inhibitor0.8956
CYP450 2D6 inhibitorNon-inhibitor0.9433
CYP450 2C19 inhibitorNon-inhibitor0.8277
CYP450 3A4 inhibitorNon-inhibitor0.9285
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8253
Ames testNon AMES toxic0.7837
CarcinogenicityNon-carcinogens0.9508
BiodegradationReady biodegradable0.9056
Rat acute toxicity1.9355 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9424
hERG inhibition (predictor II)Non-inhibitor0.9496
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
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids and derivatives
Alternative Parents
Alpha amino acid esters / Acyl-L-homoserine lactones / N-acyl amines / Gamma butyrolactones / 1,3-dicarbonyl compounds / Tetrahydrofurans / Secondary carboxylic acid amides / Ketones / Carboxylic acid esters / Oxacyclic compounds
show 5 more
Substituents
Alpha-amino acid ester / N-acyl-alpha amino acid or derivatives / Acyl-homoserine lactone / Acyl-l-homoserine lactone / Fatty amide / Gamma butyrolactone / Fatty acyl / 1,3-dicarbonyl compound / N-acyl-amine / Tetrahydrofuran
show 17 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
N-acyl-L-homoserine lactone, N-(3-oxododecanoyl)homoserine lactone (CHEBI:44534) / Fatty acyl homoserine lactones (LMFA08030001)

Targets

Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Transcription factor activity, sequence-specific dna binding
Specific Function
Transcriptional activator of elastase structural gene (LasB). Binds to the PAI autoinducer.
Gene Name
lasR
Uniprot ID
P25084
Uniprot Name
Transcriptional activator protein LasR
Molecular Weight
26618.3 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. [PubMed:10592235]

Drug created on September 15, 2010 15:30 / Updated on December 01, 2017 16:03