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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:18 UTC
HMDB IDHMDB15538
Secondary Accession NumbersNone
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
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 KeyInChIKey=GUHPRPJDBZHYCJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAcetophenones
Direct ParentAcetophenones
Alternative Parents
Substituents
  • Acetophenone
  • Aryl ketone
  • Thiophene carboxylic acid or derivatives
  • Benzoyl
  • 2,5-disubstituted thiophene
  • Heteroaromatic compound
  • Thiophene
  • Ketone
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
BiofunctionNot Available
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point96 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.24e-02 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.032 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity69.19 m3·mol-1ChemAxon
Polarizability26.78 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tiaprofenic Acid Action PathwaySMP00705Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01600
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01600
  • Not Applicable
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
NuGOwiki LinkHMDB15538
Metagene LinkHMDB15538
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. [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. [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. [2277128 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [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. [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. [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. [14987823 ]
  4. Hillarp A: [Acetylsalicylic acid resistance--clinical diagnosis with unclear mechanism]. Lakartidningen. 2004 Nov 4;101(45):3504-6, 3508-9. [15575422 ]