NAV

(4R)-limonene

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
(4R)-limonene
DrugBank Accession Number
DB08921
Background

Limonene is common in cosmetic products. As the main odor constituent of citrus (plant family Rutaceae), D-limonene is used in food manufacturing and some medicines, e.g. as a flavoring to mask the bitter taste of alkaloids, and as a fragrant in perfumery.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 136.234
Monoisotopic: 136.125200512
Chemical Formula
C10H16
Synonyms
  • (+)-(4R)-Limonene
  • (+)-(R)-Limonene
  • (+)-4-isopropenyl-1-methylcyclohexene
  • (+)-Limonene
  • (4R)-1-methyl-4-isopropenylcyclohex-1-ene
  • (4R)-4-isopropenyl-1-methylcyclohexene
  • (R)-(+)-limonene
  • (R)-(+)-p-mentha-1,8-diene
  • (R)-1-methyl-4-(1-methylethenyl)cyclohexene
  • (R)-4-isopropenyl-1-methyl-1-cyclohexene
  • (R)-p-mentha-1,8-diene
  • 4βH-p-mentha-1,8-diene
  • D-(+)-limonene
  • D-Limonen
  • D-limonene
External IDs
  • FEMA NO. 2633
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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

Hover over products below to view reaction partners

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

Products

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Purifying Balance Soothing Peeling PadLiquid0.00185573 g/100mLTopicalinthismorning co ltd2023-01-15Not applicableUS flag
Purifying Balance Soothing Peeling PadLiquid0.005016382 g/100mLTopicalinthismorning co ltd2023-01-15Not applicableUS flag
Purifying S.O.S spotgelGel0.005016382 g/100mLTopicalinthismorning co ltd2023-01-15Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Purifying Balance Soothing Peeling Pad(4R)-limonene (0.00185573 g/100mL)LiquidTopicalinthismorning co ltd2023-01-15Not applicableUS flag
Purifying Balance Soothing Peeling Pad(4R)-limonene (0.005016382 g/100mL)LiquidTopicalinthismorning co ltd2023-01-15Not applicableUS flag
Purifying S.O.S spotgel(4R)-limonene (0.005016382 g/100mL)GelTopicalinthismorning co ltd2023-01-15Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Menthane monoterpenoids
Alternative Parents
Monocyclic monoterpenoids / Branched unsaturated hydrocarbons / Cycloalkenes / Unsaturated aliphatic hydrocarbons
Substituents
Aliphatic homomonocyclic compound / Branched unsaturated hydrocarbon / Cyclic olefin / Cycloalkene / Hydrocarbon / Monocyclic monoterpenoid / Olefin / P-menthane monoterpenoid / Unsaturated aliphatic hydrocarbon / Unsaturated hydrocarbon
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
limonene (CHEBI:15382) / Menthane monoterpenoids, Cyclic monoterpenes (C06099) / Menthane monoterpenoids (LMPR0102090013)
Affected organisms
Not Available

Chemical Identifiers

UNII
GFD7C86Q1W
CAS number
5989-27-5
InChI Key
XMGQYMWWDOXHJM-JTQLQIEISA-N
InChI
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1
IUPAC Name
(4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
SMILES
CC(=C)[C@@H]1CCC(C)=CC1

References

General References
Not Available
Human Metabolome Database
HMDB0004321
KEGG Drug
D00194
KEGG Compound
C06099
ChemSpider
389747
RxNav
1426476
ChEBI
15382
ChEMBL
CHEMBL449062
ZINC
ZINC000000967513
PDBe Ligand
9IR
Wikipedia
Limonene
PDB Entries
7sji

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentGenital Human Papilloma Virus Infection1
1RecruitingSupportive CareDry Mouth1
0CompletedOtherParotid Gland Tumor / Submandibular Gland Tumor1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LiquidTopical0.00185573 g/100mL
LiquidTopical0.005016382 g/100mL
GelTopical0.005016382 g/100mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.457 mg/mLALOGPS
logP4.5ALOGPS
logP3.22Chemaxon
logS-2.5ALOGPS
Physiological Charge0Chemaxon
Hydrogen Acceptor Count0Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area0 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity46.48 m3·mol-1Chemaxon
Polarizability17.55 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9200000000-df40612bbf371089d7ac
GC-MS Spectrum - EI-BGC-MSsplash10-0173-9100000000-239928f205c8242a700a
GC-MS Spectrum - EI-BGC-MSsplash10-014l-9100000000-507f7afbc17b7c2556e2
GC-MS Spectrum - EI-BGC-MSsplash10-014l-9100000000-1a0c62c6971532ab6782
Mass Spectrum (Electron Ionization)MSsplash10-014l-9100000000-fbf154446f93ee5019c0
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000i-6900000000-f7ee4bad43b6ccae0ccb
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00ou-9000000000-51a52c25a98124e179e9
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-9655665d3d36755028cc
MS/MS Spectrum - EI-B (HITACHI RMU-6M) , PositiveLC-MS/MSsplash10-0173-9100000000-239928f205c8242a700a
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-014l-9100000000-bc8708fdb2d1955dce92
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-014l-9100000000-1a0c62c6971532ab6782
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0537-9300000000-a3bd1b7f5dc1c49edf84
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-5377e9302b4442c6b601
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1900000000-ee304ec31b45208e5c05
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-055g-9100000000-839c993bd066789c2b1a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9300000000-bffa6095d32ec3fc2f3c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-056u-9100000000-f048132828b7352e7a64
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-132.6710023
predicted
DarkChem Lite v0.1.0
[M-H]-132.3857023
predicted
DarkChem Lite v0.1.0
[M-H]-132.1641023
predicted
DarkChem Lite v0.1.0
[M-H]-132.0589023
predicted
DarkChem Lite v0.1.0
[M-H]-131.82327
predicted
DeepCCS 1.0 (2019)
[M+H]+134.48186
predicted
DeepCCS 1.0 (2019)
[M+Na]+142.80159
predicted
DeepCCS 1.0 (2019)

Drug created at September 03, 2013 20:56 / Updated at June 12, 2020 16:52