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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 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
Data?1582753307
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
SurgamKegg
2-(5-Benzoyl-thiophen-2-yl)-propionateGenerator
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
TiaprofenateGenerator
FlanidHMDB
Novo-tiaprofenicHMDB
Novopharm brand OF tiaprofenic acidHMDB
Nu-pharm brand OF tiaprofenic acidHMDB
Apotex brand OF tiaprofenic acidHMDB
Florizel brand OF tiaprofenic acidHMDB
Nu-tiaprofenicHMDB
PMS-TiaprofenicHMDB
Pierre fabre brand OF tiaprofenic acidHMDB
Surgam saHMDB
Hoechst brand OF tiaprofenic acidHMDB
Tiaprofenic acid, calcium saltHMDB
Apo-tiaprofenicHMDB
Aventis brand OF tiaprofenic acidHMDB
Grünenthal brand OF tiaprofenic acidHMDB
Pharmascience brand OF tiaprofenic acidHMDB
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
Description Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl 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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point96 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.032 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM155.130932474
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+161.59231661259
DarkChem[M-H]-156.3631661259
DeepCCS[M+H]+158.81230932474
DeepCCS[M-H]-156.43630932474
DeepCCS[M-2H]-189.32530932474
DeepCCS[M+Na]+164.88730932474
AllCCS[M+H]+157.232859911
AllCCS[M+H-H2O]+153.332859911
AllCCS[M+NH4]+160.832859911
AllCCS[M+Na]+161.832859911
AllCCS[M-H]-158.932859911
AllCCS[M+Na-2H]-158.632859911
AllCCS[M+HCOO]-158.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tiaprofenic acidCC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C13352.2Standard polar33892256
Tiaprofenic acidCC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C12086.6Standard non polar33892256
Tiaprofenic acidCC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C12310.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tiaprofenic acid,1TMS,isomer #1CC(C(=O)O[Si](C)(C)C)C1=CC=C(C(=O)C2=CC=CC=C2)S12302.9Semi standard non polar33892256
Tiaprofenic acid,1TBDMS,isomer #1CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C(=O)C2=CC=CC=C2)S12576.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tiaprofenic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0940000000-af8bb733f12381a53b772017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tiaprofenic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0avi-9841000000-6fb4e6ade76555e663612017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tiaprofenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tiaprofenic acid LC-ESI-qTof , Positive-QTOFsplash10-0a5i-3910000000-04c8e1561815c7f17b732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tiaprofenic acid , positive-QTOFsplash10-0a5i-3910000000-04c8e1561815c7f17b732017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tiaprofenic acid 10V, Positive-QTOFsplash10-03dl-1290000000-4ce6a76b25a3d1ea274f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tiaprofenic acid 20V, Positive-QTOFsplash10-0a4i-1940000000-e88e22a1c68d100554992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tiaprofenic acid 40V, Positive-QTOFsplash10-0a4i-4900000000-a38f06fe68a7ee88e1762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tiaprofenic acid 10V, Negative-QTOFsplash10-0a4i-0290000000-af1e36a58a24632536342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tiaprofenic acid 20V, Negative-QTOFsplash10-0aor-2590000000-dbee76c4fb0af7803d2b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tiaprofenic acid 40V, Negative-QTOFsplash10-0209-9600000000-b93bd531d72f525db7832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tiaprofenic acid 10V, Positive-QTOFsplash10-03di-0190000000-4f1c21443d308d90a7502021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tiaprofenic acid 20V, Positive-QTOFsplash10-0bt9-0950000000-471acf2d473bc63acf2d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tiaprofenic acid 40V, Positive-QTOFsplash10-0bvi-5900000000-3d36668b5e4c2ad9932d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tiaprofenic acid 10V, Negative-QTOFsplash10-0a4i-0290000000-5f4a79f89b41db1b68912021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tiaprofenic acid 20V, Negative-QTOFsplash10-066r-3690000000-a8ca17657d6b336059d22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tiaprofenic acid 40V, Negative-QTOFsplash10-055r-4900000000-65cdb9866d1499986d322021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01600 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01600 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01600
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]