NAV

4-Oxoretinol

Identification

Generic Name
4-Oxoretinol
DrugBank Accession Number
DB02699
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 300.4351
Monoisotopic: 300.20893014
Chemical Formula
C20H28O2
Synonyms
Not Available
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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
PathwayCategory
Retinol MetabolismMetabolic
Vitamin A DeficiencyDisease
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.
DrugInteraction
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interactions in your software
Cyproterone acetateThe therapeutic efficacy of Cyproterone acetate can be decreased when used in combination with 4-Oxoretinol.
DemeclocyclineThe risk or severity of pseudotumor cerebri can be increased when 4-Oxoretinol is combined with Demeclocycline.
DesogestrelThe therapeutic efficacy of Desogestrel can be decreased when used in combination with 4-Oxoretinol.
DienogestThe therapeutic efficacy of Dienogest can be decreased when used in combination with 4-Oxoretinol.
DiethylstilbestrolThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with 4-Oxoretinol.
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 / Fatty alcohols / Cyclohexenones / Primary alcohols / Organic oxides / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic homomonocyclic compound / Carbonyl group / Cyclic ketone / Cyclohexenone / Diterpenoid / Fatty acyl / Fatty alcohol / Hydrocarbon derivative / Ketone
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
retinoid (CHEBI:44597) / Retinoids (C16683)
Affected organisms
Not Available

Chemical Identifiers

UNII
6FFM6M3NPT
CAS number
62702-55-0
InChI Key
PLIUCYCUYQIBDZ-RMWYGNQTSA-N
InChI
InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+
IUPAC Name
3-[(1E,3E,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one
SMILES
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C

References

General References
Not Available
Human Metabolome Database
HMDB0012329
KEGG Compound
C16683
PubChem Compound
5289090
PubChem Substance
46506951
ChemSpider
4451124
ChEBI
44597
ZINC
ZINC000012502479
PDBe Ligand
OXR
PDB Entries
1x8l

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 Solubility0.0121 mg/mLALOGPS
logP5.31ALOGPS
logP4.03Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)16.44Chemaxon
pKa (Strongest Basic)-2.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity98.62 m3·mol-1Chemaxon
Polarizability36.68 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9975
Blood Brain Barrier+0.8978
Caco-2 permeable+0.8156
P-glycoprotein substrateNon-substrate0.5424
P-glycoprotein inhibitor INon-inhibitor0.6712
P-glycoprotein inhibitor IINon-inhibitor0.7751
Renal organic cation transporterNon-inhibitor0.7733
CYP450 2C9 substrateNon-substrate0.8048
CYP450 2D6 substrateNon-substrate0.8559
CYP450 3A4 substrateSubstrate0.6797
CYP450 1A2 substrateNon-inhibitor0.6685
CYP450 2C9 inhibitorNon-inhibitor0.8946
CYP450 2D6 inhibitorNon-inhibitor0.8688
CYP450 2C19 inhibitorNon-inhibitor0.873
CYP450 3A4 inhibitorNon-inhibitor0.7559
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8702
Ames testNon AMES toxic0.6933
CarcinogenicityNon-carcinogens0.8055
BiodegradationReady biodegradable0.7484
Rat acute toxicity1.7980 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8997
hERG inhibition (predictor II)Non-inhibitor0.8974
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-1290000000-4649d7f3ab4f61c01faf
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-05ns-0890000000-e9b232f9185eb8fd595f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-066r-0090000000-5f3288d6f55b38f48077
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-067i-0190000000-52771a1dd74ee12792de
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gbj-1980000000-cf3db67523c69cb04b67
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfu-0390000000-4f577f46dd2c4453f50c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0i9c-2950000000-7044b059ab59f9ee5b9d
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]-194.5101981
predicted
DarkChem Lite v0.1.0
[M-H]-206.1174981
predicted
DarkChem Lite v0.1.0
[M-H]-186.19283
predicted
DeepCCS 1.0 (2019)
[M+H]+194.2759981
predicted
DarkChem Lite v0.1.0
[M+H]+207.2951981
predicted
DarkChem Lite v0.1.0
[M+H]+188.55084
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.4268981
predicted
DarkChem Lite v0.1.0
[M+Na]+205.9215981
predicted
DarkChem Lite v0.1.0
[M+Na]+195.34741
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:45