NAV

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

Identification

Generic Name
N-[(1R,2R,3E)-2-hydroxy-1-(hydroxymethyl)heptadec-3-en-1-yl]acetamide
DrugBank Accession Number
DB06960
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 341.5286
Monoisotopic: 341.292994119
Chemical Formula
C20H39NO3
Synonyms
Not Available
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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 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
Acetamide / Alcohol / Aliphatic acyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Ceramide / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@@](O)(\C=C\CCCCCCCCCCCCC)[C@@]([H])(CO)NC(C)=O

References

General References
Not Available
PubChem Compound
12302745
PubChem Substance
99443431
ChemSpider
25061200
ZINC
ZINC000008830549
PDBe Ligand
2ED
PDB Entries
2zxc

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 Solubility0.00296 mg/mLALOGPS
logP5.27ALOGPS
logP4.39Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)13.59Chemaxon
pKa (Strongest Basic)-1.5Chemaxon
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-MSsplash10-000i-5491000000-7e609e37559caf30df36
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-1029000000-72da5a31d10585665904
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-0069000000-9e346c02fedda7c13cbc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-059x-9054000000-324f8388af5fc13fba5f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-5279000000-5e03c0b467a1129c1882
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-9150000000-8ba2989df2b8abe0d284
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9310000000-064af2f6458cce5ad2bc
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]-188.5844
predicted
DeepCCS 1.0 (2019)
[M+H]+191.608
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.7018
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Neutral ceramidase
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. [Article]

Drug created at September 15, 2010 21:18 / Updated at June 12, 2020 16:52