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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:47:12 UTC
HMDB IDHMDB0014798
Secondary Accession Numbers
  • HMDB14798
Metabolite Identification
Common NameMetaxalone
DescriptionMetaxalone (marketed by King Pharmaceuticals under the brand name Skelaxin) is a muscle relaxant used to relax muscles and relieve pain caused by strains, sprains, and other musculoskeletal conditions. Its exact mechanism of action is not known, but it may be due to general central nervous system depression. It is considered to be a moderately strong muscle relaxant, with relatively low incidence of side effects. Skelaxin comes in an 800 mg scored tablet. It previously came in both 400 mg and 800 mg tablets. The 400 mg tablet has been discontinued. Possible side effects include nausea, vomiting, drowsiness and CNS side effects such as dizziness, headache, and irritability.
Structure
Data?1582753221
Synonyms
ValueSource
SkelaxinKegg
MetassaloneHMDB
MetaxalonHMDB
MetazaloneHMDB
MetazoloneHMDB
MethaxalonumHMDB
MethoxoloneHMDB
AHR 438HMDB
Chemical FormulaC12H15NO3
Average Molecular Weight221.2524
Monoisotopic Molecular Weight221.105193351
IUPAC Name5-(3,5-dimethylphenoxymethyl)-1,3-oxazolidin-2-one
Traditional Namemetaxalone
CAS Registry Number1665-48-1
SMILES
CC1=CC(OCC2CNC(=O)O2)=CC(C)=C1
InChI Identifier
InChI=1S/C12H15NO3/c1-8-3-9(2)5-10(4-8)15-7-11-6-13-12(14)16-11/h3-5,11H,6-7H2,1-2H3,(H,13,14)
InChI KeyIMWZZHHPURKASS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • M-xylene
  • Xylene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Oxazoline
  • Ether
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point122 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.28 g/LNot Available
LogP2.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.28 g/LALOGPS
logP10(1.63) g/LALOGPS
logP10(2.37) g/LChemAxon
logS10(-2.2) g/LALOGPS
pKa (Strongest Acidic)13.14ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.56 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.32 m³·mol⁻¹ChemAxon
Polarizability23.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.52231661259
DarkChem[M-H]-151.17231661259
DeepCCS[M+H]+152.18830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MetaxaloneCC1=CC(OCC2CNC(=O)O2)=CC(C)=C13131.4Standard polar33892256
MetaxaloneCC1=CC(OCC2CNC(=O)O2)=CC(C)=C12133.2Standard non polar33892256
MetaxaloneCC1=CC(OCC2CNC(=O)O2)=CC(C)=C12236.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Metaxalone,1TMS,isomer #1CC1=CC(C)=CC(OCC2CN([Si](C)(C)C)C(=O)O2)=C12048.1Semi standard non polar33892256
Metaxalone,1TMS,isomer #1CC1=CC(C)=CC(OCC2CN([Si](C)(C)C)C(=O)O2)=C12094.4Standard non polar33892256
Metaxalone,1TMS,isomer #1CC1=CC(C)=CC(OCC2CN([Si](C)(C)C)C(=O)O2)=C12566.0Standard polar33892256
Metaxalone,1TBDMS,isomer #1CC1=CC(C)=CC(OCC2CN([Si](C)(C)C(C)(C)C)C(=O)O2)=C12281.4Semi standard non polar33892256
Metaxalone,1TBDMS,isomer #1CC1=CC(C)=CC(OCC2CN([Si](C)(C)C(C)(C)C)C(=O)O2)=C12318.5Standard non polar33892256
Metaxalone,1TBDMS,isomer #1CC1=CC(C)=CC(OCC2CN([Si](C)(C)C(C)(C)C)C(=O)O2)=C12704.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Metaxalone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-6910000000-3d869a9d7711ed9017fe2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metaxalone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metaxalone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone LC-ESI-QFT , negative-QTOFsplash10-00di-0490000000-964e6b5348bafc1182d92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone LC-ESI-QFT , negative-QTOFsplash10-0089-0980000000-2b6e14f3b5e5c19c4e5c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone LC-ESI-QFT , negative-QTOFsplash10-001i-0910000000-c8b21539b07eb2e7d34e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone LC-ESI-QFT , negative-QTOFsplash10-001i-0900000000-0f09eb181838526daa7c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone LC-ESI-QFT , negative-QTOFsplash10-001i-0900000000-018693fc5b6345ee25c52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone LC-ESI-QFT , negative-QTOFsplash10-001i-0900000000-921f9f6e188e7466aa4d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone LC-ESI-QFT , positive-QTOFsplash10-08fr-4900000000-222616eabf1bcdd480492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone LC-ESI-QFT , positive-QTOFsplash10-08fr-6900000000-06981ad91bcbeda7d3852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone LC-ESI-QFT , positive-QTOFsplash10-0a4i-6900000000-77e22c24cb4c6bbc81a12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone LC-ESI-QFT , positive-QTOFsplash10-0a4i-8900000000-54c62bf2b5c1b70898bb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone LC-ESI-QFT , positive-QTOFsplash10-0a4i-9700000000-82878fa5fbb78b27ef0b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone LC-ESI-QFT , positive-QTOFsplash10-0a4i-9500000000-66f674cba4e44834a4252017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone 90V, Positive-QTOFsplash10-0a4i-9500000000-66f674cba4e44834a4252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone 75V, Positive-QTOFsplash10-0a4i-9700000000-82878fa5fbb78b27ef0b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone 15V, Negative-QTOFsplash10-00di-0490000000-2d083d9993763dd191db2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone 30V, Negative-QTOFsplash10-0089-0980000000-2b6e14f3b5e5c19c4e5c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone 90V, Negative-QTOFsplash10-001i-0900000000-921f9f6e188e7466aa4d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone 75V, Negative-QTOFsplash10-001i-0900000000-018693fc5b6345ee25c52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metaxalone 45V, Negative-QTOFsplash10-001i-0910000000-c8b21539b07eb2e7d34e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metaxalone 10V, Positive-QTOFsplash10-00di-2390000000-78910ab75d3c3186356d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metaxalone 20V, Positive-QTOFsplash10-0fk9-1940000000-63ed5a7012ac998bf0302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metaxalone 40V, Positive-QTOFsplash10-05fr-9700000000-8a760098dec4bfd605be2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metaxalone 10V, Negative-QTOFsplash10-00di-5970000000-e23b204a74eee96b313c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metaxalone 20V, Negative-QTOFsplash10-00di-2900000000-1eddeb67df5eaa138f6c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metaxalone 40V, Negative-QTOFsplash10-00di-4900000000-d964ecadca1a428962492016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00660 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00660 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00660
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID14709
KEGG Compound IDC07934
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetaxalone
METLIN IDNot Available
PubChem Compound15459
PDB IDNot Available
ChEBI ID711679
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Elenbaas JK: Centrally acting oral skeletal muscle relaxants. Am J Hosp Pharm. 1980 Oct;37(10):1313-23. [PubMed:6999895 ]
  2. See S, Ginzburg R: Choosing a skeletal muscle relaxant. Am Fam Physician. 2008 Aug 1;78(3):365-70. [PubMed:18711953 ]