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Record Information
Version4.0
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-09-27 08:27:59 UTC
HMDB IDHMDB0015538
Secondary Accession Numbers
  • HMDB15538
Metabolite Identification
Common NameTiaprofenic acid
DescriptionTiaprofenic acid is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory drug of the arylpropionic acid (profen) class, used to treat pain, especially arthritic pain.Tiaprofenic acid belongs to a group of medicines called non-steroidal anti-inflammatory drugs (NSAIDs). It works by blocking the production of a chemical (prostaglandin) which the body produces in response to injury or certain diseases. This prostaglandin would otherwise go on to cause swelling, pain and inflammation.
Structure
Thumb
Synonyms
ValueSource
2-(5-Benzoyl-thiophen-2-yl)-propionic acidChEBI
2-(5-Benzyl-2-thienyl)propionsaeureChEBI
5-Benzoyl-alpha-methyl-2-thiopheneacetic acidChEBI
5-Benzoyl-alpha-methylthiophene-2-acetic acidChEBI
Acide tiaprofeniqueChEBI
acido TiaprofenicoChEBI
Acidum tiaprofenicumChEBI
alpha-Methyl-5-benzoyl-2-thienylacetic acidChEBI
TiaprofensaeureChEBI
2-(5-Benzoyl-thiophen-2-yl)-propionateGenerator
TiaprofenateGenerator
5-Benzoyl-a-methyl-2-thiopheneacetateGenerator
5-Benzoyl-a-methyl-2-thiopheneacetic acidGenerator
5-Benzoyl-alpha-methyl-2-thiopheneacetateGenerator
5-Benzoyl-α-methyl-2-thiopheneacetateGenerator
5-Benzoyl-α-methyl-2-thiopheneacetic acidGenerator
5-Benzoyl-a-methylthiophene-2-acetateGenerator
5-Benzoyl-a-methylthiophene-2-acetic acidGenerator
5-Benzoyl-alpha-methylthiophene-2-acetateGenerator
5-Benzoyl-α-methylthiophene-2-acetateGenerator
5-Benzoyl-α-methylthiophene-2-acetic acidGenerator
a-Methyl-5-benzoyl-2-thienylacetateGenerator
a-Methyl-5-benzoyl-2-thienylacetic acidGenerator
alpha-Methyl-5-benzoyl-2-thienylacetateGenerator
α-methyl-5-benzoyl-2-thienylacetateGenerator
α-methyl-5-benzoyl-2-thienylacetic acidGenerator
FlanidMeSH
novo-TiaprofenicMeSH
Novopharm brand OF tiaprofenic acidMeSH
Nu-pharm brand OF tiaprofenic acidMeSH
Apotex brand OF tiaprofenic acidMeSH
Florizel brand OF tiaprofenic acidMeSH
Nu-tiaprofenicMeSH
PMS-TiaprofenicMeSH
Pierre fabre brand OF tiaprofenic acidMeSH
Surgam saMeSH
Hoechst brand OF tiaprofenic acidMeSH
SurgamMeSH
Tiaprofenic acid, calcium saltMeSH
apo-TiaprofenicMeSH
Aventis brand OF tiaprofenic acidMeSH
Grünenthal brand OF tiaprofenic acidMeSH
Pharmascience brand OF tiaprofenic acidMeSH
Chemical FormulaC14H12O3S
Average Molecular Weight260.308
Monoisotopic Molecular Weight260.05071494
IUPAC Name2-(5-benzoylthiophen-2-yl)propanoic acid
Traditional Nametiaprofenic acid
CAS Registry Number33005-95-7
SMILES
CC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C14H12O3S/c1-9(14(16)17)11-7-8-12(18-11)13(15)10-5-3-2-4-6-10/h2-9H,1H3,(H,16,17)
InChI KeyGUHPRPJDBZHYCJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentAryl-phenylketones
Alternative Parents
Substituents
  • Aryl-phenylketone
  • Thiophene carboxylic acid or derivatives
  • Benzoyl
  • 2,5-disubstituted thiophene
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Thiophene
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point96 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.032 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP3.22ALOGPS
logP3.66ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.03ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity69.19 m³·mol⁻¹ChemAxon
Polarizability26.78 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0a4i-0940000000-af8bb733f12381a53b77View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0avi-9841000000-6fb4e6ade76555e66361View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a5i-3910000000-04c8e1561815c7f17b73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a5i-3910000000-04c8e1561815c7f17b73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-1290000000-4ce6a76b25a3d1ea274fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1940000000-e88e22a1c68d10055499View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-a38f06fe68a7ee88e176View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0290000000-af1e36a58a2463253634View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-2590000000-dbee76c4fb0af7803d2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0209-9600000000-b93bd531d72f525db783View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Tiaprofenic Acid Action PathwayPw000682Pw000682 greyscalePw000682 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01600 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01600 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01600
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5269
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTiaprofenic_acid
METLIN IDNot Available
PubChem Compound5468
PDB IDNot Available
ChEBI ID32221
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Brandt KD, Albrecht ME, Kalasinski LA: Effects of tiaprofenic acid on the concentration and metabolism of proteoglycans in normal and degenerating canine articular cartilage. J Clin Pharmacol. 1990 Sep;30(9):808-14. [PubMed:2277128 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Patrignani P: Aspirin insensitive eicosanoid biosynthesis in cardiovascular disease. Thromb Res. 2003 Jun 15;110(5-6):281-6. [PubMed:14592549 ]
  2. Gupta K, Kaub CJ, Carey KN, Casillas EG, Selinsky BS, Loll PJ: Manipulation of kinetic profiles in 2-aryl propionic acid cyclooxygenase inhibitors. Bioorg Med Chem Lett. 2004 Feb 9;14(3):667-71. [PubMed:14741265 ]
  3. Martic M, Tatic I, Markovic S, Kujundzic N, Kostrun S: Synthesis, biological activity and molecular modeling studies of novel COX-1 inhibitors. Eur J Med Chem. 2004 Feb;39(2):141-51. [PubMed:14987823 ]
  4. Hillarp A: [Acetylsalicylic acid resistance--clinical diagnosis with unclear mechanism]. Lakartidningen. 2004 Nov 4;101(45):3504-6, 3508-9. [PubMed:15575422 ]