NAV

N-Ethylretinamide

Identification

Generic Name
N-Ethylretinamide
DrugBank Accession Number
DB03917
Background

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

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 327.5035
Monoisotopic: 327.256214683
Chemical Formula
C22H33NO
Synonyms
  • all-trans-N-Ethylretinamide
  • Ethyl retinamide
  • Vitamin A acid ethylamide
External IDs
  • Ro 8-4968
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Pharmacology

Indication

Not Available

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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

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 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
Aliphatic homomonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Diterpenoid / Hydrocarbon derivative / N-acyl-amine / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
6LM987K76Y
CAS number
33631-41-3
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

References

General References
Not Available
PubChem Compound
5288173
PubChem Substance
46506461
ChemSpider
4450394
BindingDB
50092057
ChEMBL
CHEMBL418471
ZINC
ZINC000012504028
PDBe Ligand
ETR
PDB Entries
1erb

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 Solubility0.00332 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/MSsplash10-02a9-0491000000-416685bceaa60d8385b1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-2091000000-87630087585d7cc50f93
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9081000000-ebba4cb698c1d093d18e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1590000000-b19b1a79aca5df8e43f3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9220000000-88c2bc325f987646483c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0596-3941000000-7456d74a2694c3ba7954
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]-194.77382
predicted
DeepCCS 1.0 (2019)
[M+H]+197.13182
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.22966
predicted
DeepCCS 1.0 (2019)

Carriers

Details1. Retinol-binding protein 4
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. [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]
  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. [Article]

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