Nabumetone (CHEM018342)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:10:14 UTC
Update Date2016-11-09 01:15:47 UTC
Accession NumberCHEM018342
Identification
Common NameNabumetone
ClassSmall Molecule
DescriptionNabumetone was originally developed as a non-acidic non-steroidal anti-inflammatory drug (NSAID). It was thought to avoid trapping of the drug in the stomach by making it unable to dissociate into ions which was believed to reduce GI toxicity by limiting local action. While slightly reduced, possibly due to a degree of cyclooxygenase-2 selectivity (COX-2), nabumetone still produces significant adverse effects in the GI tract. The molecule itself is a pro-drug with its 6-methoxy-2-naphthylacetic acid (6-MNA) metabolite acting as a potent COX inhibitor similar in structure to . Nabumetone was developed by Smithkline Beecham under the trade name Nabumetone and first received FDA approval in December, 1991.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(6-Methoxy-2-naphthalenyl)-2-butanoneChEBI
4-(6-Methoxy-2-naphthyl)-2-butanoneChEBI
NabumetonaChEBI
NabumetonumChEBI
RelafenChEBI
ArthraxanHMDB
ListranHMDB
NabumetonHMDB
Apo-nabumetoneHMDB
NabucoxHMDB
RelifHMDB
MebutanHMDB
Rhoxal-nabumetoneHMDB
Gen-nabumetoneHMDB
RelifexHMDB
Rhoxal nabumetoneHMDB
ApoNabumetoneHMDB
Chemical FormulaC15H16O2
Average Molecular Mass228.286 g/mol
Monoisotopic Mass228.115 g/mol
CAS Registry Number42924-53-8
IUPAC Name4-(6-methoxynaphthalen-2-yl)butan-2-one
Traditional Namenabumetone
SMILESCOC1=CC2=C(C=C1)C=C(CCC(C)=O)C=C2
InChI IdentifierInChI=1S/C15H16O2/c1-11(16)3-4-12-5-6-14-10-15(17-2)8-7-13(14)9-12/h5-10H,3-4H2,1-2H3
InChI KeyBLXXJMDCKKHMKV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Anisole
  • Alkyl aryl ether
  • Ketone
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0019 g/LALOGPS
logP3.41ALOGPS
logP3.22ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)19.59ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.43 m³·mol⁻¹ChemAxon
Polarizability26.17 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7930000000-53550e3b73002ac9c671Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0900000000-af6f3d0d1c5f77f47279Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0900000000-6b7de93b51a79132630fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-4910000000-a4f59053ed0ee04bb88fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0900000000-6b7de93b51a79132630fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0900000000-af6f3d0d1c5f77f47279Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00fr-2900000000-53d7d6dc809a154d16c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0190000000-b864e89d948e8076c3fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-1290000000-657a908ca7f06b7711a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-3900000000-86bd2c983b81aa7bef16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-4938674275db31bd9e41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0290000000-7bbcedc9462b3b3aed77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-2940000000-3cfbcbe6458c3d4b1000Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0960000000-dc5e2e6a6aaebbe05161Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0930000000-76ec0fb1eac9f0347fa1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05bo-0900000000-cbb1b90e5fe8c723de8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-202799ccfbea13f5ad79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-5960000000-d4422601462c920c62acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-63bc8342ce285796ade9Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00461
HMDB IDHMDB0014604
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNBO
Wikipedia LinkNabumetone
Chemspider ID4256
ChEBI ID7443
PubChem Compound ID4409
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21532165
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21650014
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21674107
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21898684
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22028826
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22298755
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22381180
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22605805
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22977877
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23020786
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23129452
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23132511
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23225308
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23584048
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23781467
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23781476
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23806470
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24074034
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24083957