Indoprofen (CHEM018583)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:21:44 UTC
Update Date2016-11-09 01:15:50 UTC
Accession NumberCHEM018583
Identification
Common NameIndoprofen
ClassSmall Molecule
DescriptionA monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(1-oxo-1,3-dihydroisoindol-2-yl)phenyl group. Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causing severe gastrointestinal bleeding. It has been subsequently found to increase production of the survival motor neuron protein.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-oxo-2-(p-((alpha-Methyl)carboxymethyl)phenyl)isoindolineChEBI
2-(4-(1-Carboxyethyl)phenyl)-1-isoindolinoneChEBI
alpha-(4-(1-oxo-2-Isoindolinyl)phenyl)propionic acidChEBI
IndoprofeneChEBI
IndoprofenoChEBI
IndoprofenumChEBI
K 4277ChEBI
1-oxo-2-(p-((a-Methyl)carboxymethyl)phenyl)isoindolineGenerator
1-oxo-2-(p-((Α-methyl)carboxymethyl)phenyl)isoindolineGenerator
a-(4-(1-oxo-2-Isoindolinyl)phenyl)propionateGenerator
a-(4-(1-oxo-2-Isoindolinyl)phenyl)propionic acidGenerator
alpha-(4-(1-oxo-2-Isoindolinyl)phenyl)propionateGenerator
Α-(4-(1-oxo-2-isoindolinyl)phenyl)propionateGenerator
Α-(4-(1-oxo-2-isoindolinyl)phenyl)propionic acidGenerator
DexindoprofenMeSH
Chemical FormulaC17H15NO3
Average Molecular Mass281.306 g/mol
Monoisotopic Mass281.105 g/mol
CAS Registry Number31842-01-0
IUPAC Name2-[4-(1-oxo-2,3-dihydro-1H-isoindol-2-yl)phenyl]propanoic acid
Traditional Nameindoprofen
SMILESCC(C(O)=O)C1=CC=C(C=C1)N1CC2=CC=CC=C2C1=O
InChI IdentifierInChI=1S/C17H15NO3/c1-11(17(20)21)12-6-8-14(9-7-12)18-10-13-4-2-3-5-15(13)16(18)19/h2-9,11H,10H2,1H3,(H,20,21)
InChI KeyRJMIEHBSYVWVIN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 2-phenylpropanoic-acid
  • Isoindolone
  • Isoindoline
  • Isoindole
  • Isoindole or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.13 g/LALOGPS
logP2.44ALOGPS
logP2.86ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.14 m³·mol⁻¹ChemAxon
Polarizability30.24 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-3390000000-21d1485ed2c4aa781debSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-3790000000-98b2b4d927ad1042f83fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-3790000000-98b2b4d927ad1042f83fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-af156fbb8d3094ece3c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-0490000000-b8c573a20d8de095916eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1930000000-72c08e451147331cf951Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-15cfc780c539fbf8e860Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-0290000000-4297ebba7695694f6481Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3950000000-eab255dffad7dab518a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0090000000-ca55c7a121e9a1503abfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ei-0090000000-f0e0aaad648c976ce696Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f8c-5920000000-32a6ad3d095277b87fe4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-f4d0988da0ee381b3a02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-91dffad92b62e0d4c056Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-2980000000-91e0983609c8f015d7d5Spectrum
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 IDDB08951
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIndoprofen
Chemspider IDNot Available
ChEBI ID76162
PubChem Compound ID3718
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=1017174
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22282415
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22349325
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2519164
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=2753348
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=2775332
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=369767
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=378745
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=392647
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=47280
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=550151
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=6436749
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6578800
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=7042369
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=7341277
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=7349186
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=7428321