N-Ethylretinamide

Identification

Name
N-Ethylretinamide
Accession Number
DB03917  (EXPT01372)
Type
Small Molecule
Groups
Experimental
Description

N-Ethylretinamide is the ethylamide of all-trans B-retinoic acid.

Structure
Thumb
Synonyms
  • all-trans-N-Ethylretinamide
  • Ethyl retinamide
  • Vitamin A acid ethylamide
External IDs
Ro 8-4968
Categories
UNII
6LM987K76Y
CAS number
33631-41-3
Weight
Average: 327.5035
Monoisotopic: 327.256214683
Chemical Formula
C22H33NO
InChI Key
WKYDOCGICAMTKE-NBIQJRODSA-N
InChI
InChI=1S/C22H33NO/c1-7-23-21(24)16-18(3)11-8-10-17(2)13-14-20-19(4)12-9-15-22(20,5)6/h8,10-11,13-14,16H,7,9,12,15H2,1-6H3,(H,23,24)/b11-8+,14-13+,17-10+,18-16+
IUPAC Name
(2E,4E,6E,8E)-N-ethyl-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
SMILES
CCNC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
PubChem Compound
5288173
PubChem Substance
46506461
ChemSpider
4450394
BindingDB
50092057
ChEMBL
CHEMBL418471
ZINC
ZINC000012504028
PDBe Ligand
ETR
PDB Entries
1erb

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 Solubility0.00332 mg/mLALOGPS
logP6.05ALOGPS
logP4.79ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)16.31ChemAxon
pKa (Strongest Basic)-0.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity109.26 m3·mol-1ChemAxon
Polarizability41.35 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9912
Caco-2 permeable+0.6316
P-glycoprotein substrateNon-substrate0.5714
P-glycoprotein inhibitor IInhibitor0.5609
P-glycoprotein inhibitor IIInhibitor0.5
Renal organic cation transporterNon-inhibitor0.7801
CYP450 2C9 substrateNon-substrate0.8573
CYP450 2D6 substrateNon-substrate0.7745
CYP450 3A4 substrateSubstrate0.5901
CYP450 1A2 substrateNon-inhibitor0.6692
CYP450 2C9 inhibitorNon-inhibitor0.6354
CYP450 2D6 inhibitorNon-inhibitor0.8758
CYP450 2C19 inhibitorNon-inhibitor0.6945
CYP450 3A4 inhibitorNon-inhibitor0.6581
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5861
Ames testNon AMES toxic0.8474
CarcinogenicityNon-carcinogens0.745
BiodegradationNot ready biodegradable0.5692
Rat acute toxicity2.0384 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9638
hERG inhibition (predictor II)Non-inhibitor0.8589
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 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 retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Retinoids
Direct Parent
Retinoids
Alternative Parents
Diterpenoids / N-acyl amines / Secondary carboxylic acid amides / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Retinoid skeleton / Diterpenoid / N-acyl-amine / Secondary carboxylic acid amide / Carboxamide group / Carboxylic acid derivative / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Retinol transporter activity
Specific Function
Delivers retinol from the liver stores to the peripheral tissues. In plasma, the RBP-retinol complex interacts with transthyretin, this prevents its loss by filtration through the kidney glomeruli.
Gene Name
RBP4
Uniprot ID
P02753
Uniprot Name
Retinol-binding protein 4
Molecular Weight
23009.8 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]
  3. 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 June 13, 2005 07:24 / Updated on March 01, 2020 19:16

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