NAV

(4R)-limonene 1α,2α-epoxide

Identification

Generic Name
(4R)-limonene 1α,2α-epoxide
DrugBank Accession Number
DB02924
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 152.2334
Monoisotopic: 152.120115134
Chemical Formula
C10H16O
Synonyms
  • (+)-trans-limonene oxide
  • (1S,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptane
  • (4R)-limonene 1alpha,2alpha-epoxide
  • 1α,2α-epoxy-4βH-p-menth-8-ene
  • D-limonene 1,2-epoxide
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEpididymal-specific lipocalin-9Not AvailableHumans
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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as oxepanes. These are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Oxepanes
Sub Class
Not Available
Direct Parent
Oxepanes
Alternative Parents
Oxacyclic compounds / Epoxides / Dialkyl ethers / Hydrocarbon derivatives
Substituents
Aliphatic heteropolycyclic compound / Dialkyl ether / Ether / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Oxacycle / Oxepane / Oxirane
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
(4R)-limonene 1,2-epoxide (CHEBI:35669)
Affected organisms
Not Available

Chemical Identifiers

UNII
KBX06MQJ5Y
CAS number
6909-30-4
InChI Key
CCEFMUBVSUDRLG-KXUCPTDWSA-N
InChI
InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
IUPAC Name
(1R,4R,6S)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane
SMILES
CC(=C)[C@@H]1CC[C@@]2(C)O[C@H]2C1

References

General References
Not Available
PubChem Compound
6857487
PubChem Substance
46507994
ChemSpider
5256823
ChEBI
35669
ZINC
ZINC000002545304
PDBe Ligand
GH9
PDB Entries
7t9e

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 Solubility0.351 mg/mLALOGPS
logP2.81ALOGPS
logP2.32Chemaxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area12.53 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity45.24 m3·mol-1Chemaxon
Polarizability18.19 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9818
Blood Brain Barrier+0.9626
Caco-2 permeable+0.6665
P-glycoprotein substrateSubstrate0.5882
P-glycoprotein inhibitor INon-inhibitor0.6437
P-glycoprotein inhibitor IINon-inhibitor0.8979
Renal organic cation transporterNon-inhibitor0.7839
CYP450 2C9 substrateNon-substrate0.8586
CYP450 2D6 substrateNon-substrate0.8429
CYP450 3A4 substrateSubstrate0.5669
CYP450 1A2 substrateInhibitor0.7089
CYP450 2C9 inhibitorNon-inhibitor0.5512
CYP450 2D6 inhibitorNon-inhibitor0.9316
CYP450 2C19 inhibitorInhibitor0.5571
CYP450 3A4 inhibitorNon-inhibitor0.8418
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8628
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8036
BiodegradationNot ready biodegradable0.6793
Rat acute toxicity1.6719 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8685
hERG inhibition (predictor II)Non-inhibitor0.8547
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/MSsplash10-0f79-4900000000-1a44a72e47a1c0c9fc0b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-bb0491d1e961e36f86d4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-1900000000-18772c7b4598c05a0f1c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052o-9700000000-1b2b378672722a01826b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014u-9200000000-4c3c0c906e02dffc4489
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0le9-5900000000-52972fa961bfc46d6b99
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]-135.6923868
predicted
DarkChem Lite v0.1.0
[M-H]-136.0703868
predicted
DarkChem Lite v0.1.0
[M-H]-137.2376
predicted
DeepCCS 1.0 (2019)
[M+H]+137.0244868
predicted
DarkChem Lite v0.1.0
[M+H]+136.9385868
predicted
DarkChem Lite v0.1.0
[M+H]+139.63316
predicted
DeepCCS 1.0 (2019)
[M+Na]+136.3105868
predicted
DarkChem Lite v0.1.0
[M+Na]+136.0107868
predicted
DarkChem Lite v0.1.0
[M+Na]+145.54567
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Epididymal-specific lipocalin-9
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Not Available
Gene Name
LCN9
Uniprot ID
Q8WX39
Uniprot Name
Epididymal-specific lipocalin-9
Molecular Weight
20284.895 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