N-[(1R,2R,3E)-2-hydroxy-1-(hydroxymethyl)heptadec-3-en-1-yl]acetamide

Identification

Name
N-[(1R,2R,3E)-2-hydroxy-1-(hydroxymethyl)heptadec-3-en-1-yl]acetamide
Accession Number
DB06960
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: 341.5286
Monoisotopic: 341.292994119
Chemical Formula
C20H39NO3
InChI Key
BLTCBVOJNNKFKC-KTEGJIGUSA-N
InChI
InChI=1S/C20H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h15-16,19-20,22,24H,3-14,17H2,1-2H3,(H,21,23)/b16-15+/t19-,20-/m1/s1
IUPAC Name
N-[(2R,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide
SMILES
[H][[email protected]@](O)(\C=C\CCCCCCCCCCCCC)[[email protected]@]([H])(CO)NC(C)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNeutral ceramidaseNot 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

Synthesis Reference
Not Available
General References
Not Available
External Links
PubChem Compound
12302745
PubChem Substance
99443431
ChemSpider
25061200
HET
2ED
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
2zxc
FDA label
Not Available
MSDS
Not Available

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 Solubility0.00296 mg/mLALOGPS
logP5.27ALOGPS
logP4.39ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)13.59ChemAxon
pKa (Strongest Basic)-0.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity101.34 m3·mol-1ChemAxon
Polarizability43.32 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9949
Blood Brain Barrier+0.8649
Caco-2 permeable-0.5751
P-glycoprotein substrateSubstrate0.5399
P-glycoprotein inhibitor INon-inhibitor0.8714
P-glycoprotein inhibitor IINon-inhibitor0.6249
Renal organic cation transporterNon-inhibitor0.9354
CYP450 2C9 substrateNon-substrate0.8021
CYP450 2D6 substrateNon-substrate0.7535
CYP450 3A4 substrateNon-substrate0.5984
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.6937
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.8451
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6331
Ames testNon AMES toxic0.7995
CarcinogenicityNon-carcinogens0.8416
BiodegradationReady biodegradable0.8491
Rat acute toxicity1.8415 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9828
hERG inhibition (predictor II)Non-inhibitor0.8975
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 ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Sphingolipids
Sub Class
Ceramides
Direct Parent
Ceramides
Alternative Parents
Acetamides / Secondary carboxylic acid amides / Secondary alcohols / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Ceramide / Acetamide / Carboxamide group / Secondary alcohol / Secondary carboxylic acid amide / Carboxylic acid derivative / Alcohol / Hydrocarbon derivative / Organic oxide / Primary alcohol
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the cleavage of the N-acyl linkage of the ceramides (Cers) to yield sphingosine (Sph) and free fatty acid at an optimal pH of 8-9. Also catalyzes the synthesis of Cers from Sph and fatty ...
Gene Name
Not Available
Uniprot ID
Q9I596
Uniprot Name
Neutral ceramidase
Molecular Weight
73372.125 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 15:18 / Updated on October 02, 2017 05:48