Showing metabocard for Naproxen (BMDB0001923)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:49:00 UTC
Update Date2020-05-11 20:22:52 UTC
BMDB IDBMDB0001923
Secondary Accession Numbers
  • BMDB01923
Metabolite Identification
Common NameNaproxen
DescriptionNaproxen, also known as naprosyn or (S)-naproxen, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Naproxen is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acidChEBI
(+)-(S)-NaproxenChEBI
(+)-2-(6-Methoxy-2-naphthyl)propionic acidChEBI
(+)-2-(Methoxy-2-naphthyl)-propionic acidChEBI
(+)-2-(Methoxy-2-naphthyl)-propionsaeureChEBI
(+)-NaproxenChEBI
(S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acidChEBI
(S)-(+)-NaproxenChEBI
(S)-2-(6-Methoxy-2-naphthyl)propanoic acidChEBI
(S)-2-(6-Methoxy-2-naphthyl)propionic acidChEBI
(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acidChEBI
(S)-NaproxenChEBI
NaproxeneChEBI
NaproxenoChEBI
NaproxenumChEBI
NaprosynKegg
(+)-(S)-6-Methoxy-a-methyl-2-naphthaleneacetateGenerator
(+)-(S)-6-Methoxy-a-methyl-2-naphthaleneacetic acidGenerator
(+)-(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetateGenerator
(+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetateGenerator
(+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acidGenerator
(+)-2-(6-Methoxy-2-naphthyl)propionateGenerator
(+)-2-(Methoxy-2-naphthyl)-propionateGenerator
(S)-(+)-2-(6-Methoxy-2-naphthyl)propionateGenerator
(S)-2-(6-Methoxy-2-naphthyl)propanoateGenerator
(S)-2-(6-Methoxy-2-naphthyl)propionateGenerator
(S)-6-Methoxy-a-methyl-2-naphthaleneacetateGenerator
(S)-6-Methoxy-a-methyl-2-naphthaleneacetic acidGenerator
(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetateGenerator
(S)-6-Methoxy-α-methyl-2-naphthaleneacetateGenerator
(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acidGenerator
2-(6-Methoxy-2-naphthyl)propionic acidHMDB
AcusprainHMDB
AnexopenHMDB
ApronaxHMDB
ArtagenHMDB
ArthrisilHMDB
ArtrixenHMDB
ArtroxenHMDB
AtiflanHMDB
AxerHMDB
BipronylHMDB
CalosenHMDB
ClinosynHMDB
CongexHMDB
D-NaproxenHMDB
DanaproxHMDB
DaproxHMDB
DiocodalHMDB
DL NaproxenHMDB
DL-NaproxenHMDB
DukHMDB
DysmenalgitHMDB
Dysmenalgit NHMDB
Ec-naprosynHMDB
EquiproxenHMDB
FlexipenHMDB
FloginaxHMDB
FuxenHMDB
GenoxenHMDB
LefaineHMDB
LeniartilHMDB
NafasolHMDB
NaixanHMDB
NalyxanHMDB
NapflamHMDB
NapmelHMDB
NaposinHMDB
NaprosyneHMDB
Naproxen sodiumHMDB
NovonaproxHMDB
NycoprenHMDB
OpipramolHMDB
AnaproxHMDB
MethoxypropiocinHMDB
NaprosinHMDB
ProxenHMDB
AleveHMDB
Sodium, naproxenHMDB
MNPAHMDB
SynflexHMDB
Naproxenate, sodiumHMDB
Sodium naproxenateHMDB
Chemical FormulaC14H14O3
Average Molecular Weight230.2592
Monoisotopic Molecular Weight230.094294314
IUPAC Name(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
Traditional Namenaproxen
CAS Registry Number22204-53-1
SMILES
COC1=CC2=C(C=C1)C=C(C=C2)[C@H](C)C(O)=O
InChI Identifier
InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1
InChI KeyCMWTZPSULFXXJA-VIFPVBQESA-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
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point153 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0159 mg/mL at 25 °CNot Available
LogP3.18HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP3.29ALOGPS
logP2.99ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.19ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.85 m³·mol⁻¹ChemAxon
Polarizability24.81 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0540-1920000000-dfcdd431a9b1898cd2d2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9840000000-4be264b19923ce29c773View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-001i-0190000000-64cc22cce1238357760eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0f79-0900000000-17f4e93fda31d93027a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0fr6-0900000000-4dd08568cff27d62d867View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0910000000-149b16cac2d80de64d8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0900000000-e7dfead967f29853140dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-01b9-0900000000-f5f45cee188a08ef62b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-0900000000-6c076658da1c69f1b909View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-0900000000-2e1269f26d5b927bca33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-68cd0c5a3fcc15470c14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-64e5ecb5632e32f89b2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0910000000-149b16cac2d80de64d8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-e7dfead967f29853140dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01b9-0900000000-f5f45cee188a08ef62b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-6c076658da1c69f1b909View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-2e1269f26d5b927bca33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-b913db958cba90673250View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01b9-0900000000-f35f797484d025dc2013View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004l-4900000000-e4dd2dd07b393d508ee4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0390000000-8bab8d5b4ea21227ea6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-0960000000-f66eabdbaeb345d69ff8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-0900000000-74f939f129b9072f0315View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0390000000-b9c68cf2920eb7b41eacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00n0-0950000000-7e56ebeb218436f98f52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-2910000000-2191f1b5cabc1a005c8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00n0-0920000000-eca41f81604c83496084View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Epidermis
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001923
DrugBank IDDB00788
Phenol Explorer Compound IDNot Available
FooDB IDFDB022741
KNApSAcK IDNot Available
Chemspider ID137720
KEGG Compound IDC01517
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNaproxen
METLIN ID1461
PubChem Compound156391
PDB IDNot Available
ChEBI ID7476
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available