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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:40:47 UTC
HMDB IDHMDB0015008
Secondary Accession Numbers
  • HMDB15008
Metabolite Identification
Common NameSuprofen
DescriptionSuprofen is only found in individuals that have used or taken this drug. It is an ibuprofen-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic. [PubChem]Suprofen binds to the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) isoenzymes, preventing the synthesis of prostaglandins and reducing the inflammatory response. Cyclooxygenase catalyses the formation of prostaglandins and thromboxane from arachidonic acid (itself derived from the cellular phospholipid bilayer by phospholipase A2). Prostaglandins act (among other things) as messenger molecules in the process of inflammation. The overall result is a reduction in pain and inflammation in the eyes and the prevention of pupil constriction during surgery. Normally trauma to the anterior segment of the eye (especially the iris) increases endogenous prostaglandin synthesis which leads to constriction of the iris sphincter.
Structure
Data?1582753247
Synonyms
ValueSource
(+-)-2-(p-(2-Thenoyl)phenyl)propionic acidChEBI
2-(4-(2-Thenoyl)phenyl)propionsaeureChEBI
2-[4-(Thiophene-2-carbonyl)-phenyl]-propionic acidChEBI
4-(2-Thenoyl)hydratropsaeureChEBI
alpha-Methyl-4-(2-thienylcarbonyl)benzeneacetic acidChEBI
p-2-Thenoylhydratropic acidChEBI
PROFENALChEBI
SuprofeneChEBI
SuprofenumChEBI
SUTOPROFENChEBI
(+-)-2-(p-(2-Thenoyl)phenyl)propionateGenerator
2-[4-(Thiophene-2-carbonyl)-phenyl]-propionateGenerator
a-Methyl-4-(2-thienylcarbonyl)benzeneacetateGenerator
a-Methyl-4-(2-thienylcarbonyl)benzeneacetic acidGenerator
alpha-Methyl-4-(2-thienylcarbonyl)benzeneacetateGenerator
Α-methyl-4-(2-thienylcarbonyl)benzeneacetateGenerator
Α-methyl-4-(2-thienylcarbonyl)benzeneacetic acidGenerator
p-2-ThenoylhydratropateGenerator
Chemical FormulaC14H12O3S
Average Molecular Weight260.308
Monoisotopic Molecular Weight260.05071494
IUPAC Name2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid
Traditional Namesuprofen
CAS Registry Number40828-46-4
SMILES
CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC=CS1
InChI Identifier
InChI=1S/C14H12O3S/c1-9(14(16)17)10-4-6-11(7-5-10)13(15)12-3-2-8-18-12/h2-9H,1H3,(H,16,17)
InChI KeyMDKGKXOCJGEUJW-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
  • 2-phenylpropanoic-acid
  • P-cymene
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Benzoyl
  • Thiophene carboxylic acid or derivatives
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Thiophene
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point124.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.042 g/LNot Available
LogP2.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP3.16ALOGPS
logP3.53ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.01ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity69.41 m³·mol⁻¹ChemAxon
Polarizability26.84 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03yi-3950000000-2beb7651624021d3b69cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-044r-9641000000-c830643d9eb20837ed21Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-2790000000-0cf8f983c8b216c951b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-2790000000-0cf8f983c8b216c951b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-b385b916f83fe63a391fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00pl-0980000000-8949c56f6ad00845d44fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-2910000000-beb45e1bbb9ee6cfb6d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-e899cf6b283f80af4b28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-067i-3290000000-1cda8cbaaa37e5e208a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-a847e351fd4eaab35709Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00870 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00870 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00870
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5166
KEGG Compound IDC07320
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSuprofen
METLIN IDNot Available
PubChem Compound5359
PDB IDNot Available
ChEBI ID9362
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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. Llorens O, Perez JJ, Palomer A, Mauleon D: Differential binding mode of diverse cyclooxygenase inhibitors. J Mol Graph Model. 2002 Mar;20(5):359-71. [PubMed:11885959 ]
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. Loll PJ, Picot D, Ekabo O, Garavito RM: Synthesis and use of iodinated nonsteroidal antiinflammatory drug analogs as crystallographic probes of the prostaglandin H2 synthase cyclooxygenase active site. Biochemistry. 1996 Jun 11;35(23):7330-40. [PubMed:8652509 ]
  2. Bender A, Scheiber J, Glick M, Davies JW, Azzaoui K, Hamon J, Urban L, Whitebread S, Jenkins JL: Analysis of pharmacology data and the prediction of adverse drug reactions and off-target effects from chemical structure. ChemMedChem. 2007 Jun;2(6):861-73. [PubMed:17477341 ]
  3. Llorens O, Perez JJ, Palomer A, Mauleon D: Differential binding mode of diverse cyclooxygenase inhibitors. J Mol Graph Model. 2002 Mar;20(5):359-71. [PubMed:11885959 ]
  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 monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]