Human Metabolome Database Version 3.5

Showing metabocard for Aspirin (HMDB01879)

Record Information
Version 3.5
Creation Date 2006-02-24 06:00:45 -0700
Update Date 2013-08-14 11:06:57 -0600
HMDB ID HMDB01879
Secondary Accession Numbers None
Metabolite Identification
Common Name Aspirin
Description Aspirin is only found in individuals who have consumed this drug. Aspirin or acetylsalicylic acid (acetosal) is a drug in the family of salicylates, often used as an analgesic (against minor pains and aches), antipyretic (against fever), and anti-inflammatory. It has also an anticoagulant effect and is used in long-term low-doses to prevent heart attacks and cancer. It was isolated from meadowsweet (Filipendula ulmaria, formerly classified as Spiraea ulmaria) by German researchers in 1839. While their extract was somewhat effective, it also caused digestive problems such as irritated stomach and diarrhoea, and even death when consumed in high doses. In 1853, a French chemist named Charles Frederic Gerhardt neutralized salicylic acid by buffering it with sodium (sodium salicylate) and acetyl chloride, creating acetosalicylic anhydride. Gerhardt's product worked, but he had no desire to market it and abandoned his discovery. In 1897, researcher Arthur Eichengrun and Felix Hoffmann, a research assistant at Friedrich Bayer & Co. in Germany, derivatized one of the hydroxyl functional groups in salicylic acid with an acetyl group (forming the acetyl ester), which greatly reduced the negative effects. This was the first synthetic drug, not a copy of something that existed in nature, and the start of the pharmaceuticals industry. The name 'aspirin' is composed of a- (from the acetyl group) -spir- (from the plant genus Spiraea) and -in (a common ending for drugs at the time). It has also been stated that the name originated by another means. As referring to AcetylSalicylic and 'pir' in reference to one of the scientists who was able to isolate it in crystalline form, Raffaele Piria. Finally 'in' due to the same reasons as stated above. Salicylic acid (which is a naturally occurring substance found in many plants) can be acetylated using acetic anhydride, yielding aspirin and acetic acid as a byproduct. It is a common experiment performed in organic chemistry labs, and generally tends to produce low yields due to the relative difficulty of its extraction from an aqueous state. The trick to getting the reaction to work is to acidify with phosphoric acid and heat the reagents under reflux with a boiling water bath for between 40 minutes and an hour. Aspirin acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-(Acetyloxy)benzoate
  2. 2-(Acetyloxy)benzoic acid
  3. 2-Acetoxybenzenecarboxylic acid
  4. 2-Acetoxybenzoate
  5. 2-Acetoxybenzoic acid
  6. 2-Carboxyphenyl acetate
  7. Acenterine
  8. Acetard
  9. Aceticyl
  10. Acetol
  11. Acetonyl
  12. Acetophen
  13. Acetosal
  14. Acetosalin
  15. Acetylin
  16. Acetylsalicylate
  17. Acetylsalicylic acid
  18. Acetyonyl
  19. Acetysal
  20. Acetysalicylic acid
  21. Acylpyrin
  22. Asatard
  23. Aspergum
  24. Aspirdrops
  25. Aspirin
  26. Benaspir
  27. Bialpirinia
  28. Bufferin
  29. Caprin
  30. Cardioaspirina
  31. Easprin
  32. Ecolen
  33. Ecotrin
  34. Empirin
  35. Endosprin
  36. Endydol
  37. O-(Acetyloxy)benzoate
  38. O-(Acetyloxy)benzoic acid
  39. O-Acetoxybenzoate
  40. O-Acetoxybenzoic acid
  41. O-Acetylsalicylic acid
  42. O-Carboxyphenyl acetate
  43. Persistin
  44. Pharmacin
  45. Polopiryna
  46. Premaspin
  47. Rheumintabletten
  48. Rhodine
  49. Salcetogen
  50. Saletin
  51. Salicylic acid acetate
  52. Salospir
  53. Solprin
  54. Solprin acid
  55. Solpyron
  56. Tasprin
  57. Temperal
  58. Toldex
  59. Triaminicin
Chemical Formula C9H8O4
Average Molecular Weight 180.1574
Monoisotopic Molecular Weight 180.042258744
IUPAC Name 2-(acetyloxy)benzoic acid
Traditional IUPAC Name aspirin
CAS Registry Number 50-78-2
SMILES CC(=O)OC1=CC=CC=C1C(O)=O
InChI Identifier InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
InChI Key BSYNRYMUTXBXSQ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzoic Acid and Derivatives
Sub Class Hydroxybenzoic Acid Derivatives
Other Descriptors
  • Organic Compounds
  • Phenylacetic Acid Derivatives
  • acetate ester(ChEBI)
  • benzoic acids(ChEBI)
Substituents
  • Benzoyl
  • Carboxylic Acid
  • Carboxylic Acid Ester
  • Dicarboxylic Acid Derivative
Direct Parent Salicylic Acid and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 135 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 1.19 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 1.46 g/L ALOGPS
LogP 1.43 ALOGPS
LogP 1.24 ChemAxon
LogS -2.09 ALOGPS
pKa (strongest acidic) 3.41 ChemAxon
pKa (strongest basic) -7.1 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 63.6 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 44.45 ChemAxon
Polarizability 16.8 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (Unknown)
MS/MS Spectrum CI-B (Unknown)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
Tissue Location
  • Platelet
Pathways
Name SMPDB Link KEGG Link
Acetylsalicylic Acid Pathway SMP00083 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
26.5 +/- 1.9 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00945 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB000894
KNApSAcK ID Not Available
Chemspider ID 2157 Link_out
KEGG Compound ID C01405 Link_out
BioCyc ID Not Available
BiGG ID 45400 Link_out
Wikipedia Link Aspirin Link_out
NuGOwiki Link HMDB01879 Link_out
Metagene Link HMDB01879 Link_out
METLIN ID Not Available
PubChem Compound 2244 Link_out
PDB ID AIN Link_out
ChEBI ID 15365 Link_out
References
Synthesis Reference Chen, Hong; Long, Xiang; Huang, Siqing. Synthesis of aspirin with vitamin C as catalyst. Huaxue Shijie (2004), 45(12), 642-643.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Frelinger AL 3rd, Furman MI, Linden MD, Li Y, Fox ML, Barnard MR, Michelson AD: Residual arachidonic acid-induced platelet activation via an adenosine diphosphate-dependent but cyclooxygenase-1- and cyclooxygenase-2-independent pathway: a 700-patient study of aspirin resistance. Circulation. 2006 Jun 27;113(25):2888-96. Epub 2006 Jun 19. Pubmed: 16785341 Link_out
  2. Eikelboom J, Feldman M, Mehta SR, Michelson AD, Oates JA, Topol E: Aspirin resistance and its implications in clinical practice. MedGenMed. 2005 Jul 11;7(3):76. Pubmed: 16369302 Link_out
  3. Konrad CJ, Schuepfer GK, Gerber H, Rukwied R, Schmelz M, Schley M: Duration of effects of aspirin on platelet function in healthy volunteers: an analysis using the PFA-100. J Clin Anesth. 2006 Feb;18(1):12-7. Pubmed: 16517326 Link_out
  4. Faraday N, Becker DM, Yanek LR, Herrera-Galeano JE, Segal JB, Moy TF, Bray PF, Becker LC: Relation between atherosclerosis risk factors and aspirin resistance in a primary prevention population. Am J Cardiol. 2006 Sep 15;98(6):774-9. Epub 2006 Jul 28. Pubmed: 16950183 Link_out
  5. Lee SH, Rhim T, Choi YS, Min JW, Kim SH, Cho SY, Paik YK, Park CS: Complement C3a and C4a increased in plasma of patients with aspirin-induced asthma. Am J Respir Crit Care Med. 2006 Feb 15;173(4):370-8. Epub 2005 Nov 17. Pubmed: 16293803 Link_out
  6. Perneby C, Wallen NH, Rooney C, Fitzgerald D, Hjemdahl P: Dose- and time-dependent antiplatelet effects of aspirin. Thromb Haemost. 2006 Apr;95(4):652-8. Pubmed: 16601836 Link_out
  7. Maree AO, Curtin RJ, Chubb A, Dolan C, Cox D, O'Brien J, Crean P, Shields DC, Fitzgerald DJ: Cyclooxygenase-1 haplotype modulates platelet response to aspirin. J Thromb Haemost. 2005 Oct;3(10):2340-5. Epub 2005 Sep 9. Pubmed: 16150050 Link_out
  8. Satoh K, Ozaki Y: [Attempts for aspirin monitoring with a new assay system, Ultegra Rapid Platelet Function Assay (RPFA), based on turbidimetric platelet agglutination of whole blood samples] Rinsho Byori. 2006 Jun;54(6):576-82. Pubmed: 16872006 Link_out
  9. Eikelboom JW, Hankey GJ, Thom J, Claxton A, Yi Q, Gilmore G, Staton J, Barden A, Norman PE: Enhanced antiplatelet effect of clopidogrel in patients whose platelets are least inhibited by aspirin: a randomized crossover trial. J Thromb Haemost. 2005 Dec;3(12):2649-55. Pubmed: 16359503 Link_out
  10. Cornelissen J, Kirtland S, Lim E, Goddard M, Bellm S, Sheridan K, Large S, Vuylsteke A: Biological efficacy of low against medium dose aspirin regimen after coronary surgery: analysis of platelet function. Thromb Haemost. 2006 Mar;95(3):476-82. Pubmed: 16525576 Link_out
  11. Eliasson B, Cederholm J, Nilsson P, Gudbjornsdottir S: The gap between guidelines and reality: Type 2 diabetes in a National Diabetes Register 1996-2003. Diabet Med. 2005 Oct;22(10):1420-6. Pubmed: 16176206 Link_out
  12. Zailaie MZ: Aspirin reduces serum anti-melanocyte antibodies and soluble interleukin-2 receptors in vitiligo patients. Saudi Med J. 2005 Jul;26(7):1085-91. Pubmed: 16047057 Link_out
  13. Aktas B, Pozgajova M, Bergmeier W, Sunnarborg S, Offermanns S, Lee D, Wagner DD, Nieswandt B: Aspirin induces platelet receptor shedding via ADAM17 (TACE). J Biol Chem. 2005 Dec 2;280(48):39716-22. Epub 2005 Sep 22. Pubmed: 16179345 Link_out
  14. Maree AO, Curtin RJ, Dooley M, Conroy RM, Crean P, Cox D, Fitzgerald DJ: Platelet response to low-dose enteric-coated aspirin in patients with stable cardiovascular disease. J Am Coll Cardiol. 2005 Oct 4;46(7):1258-63. Pubmed: 16198840 Link_out
  15. Lev EI, Patel RT, Maresh KJ, Guthikonda S, Granada J, DeLao T, Bray PF, Kleiman NS: Aspirin and clopidogrel drug response in patients undergoing percutaneous coronary intervention: the role of dual drug resistance. J Am Coll Cardiol. 2006 Jan 3;47(1):27-33. Epub 2005 Dec 9. Pubmed: 16386660 Link_out
  16. Sun W, Gerhardinger C, Dagher Z, Hoehn T, Lorenzi M: Aspirin at low-intermediate concentrations protects retinal vessels in experimental diabetic retinopathy through non-platelet-mediated effects. Diabetes. 2005 Dec;54(12):3418-26. Pubmed: 16306357 Link_out
  17. Markuszewski L, Rosiak M, Golanski J, Rysz J, Spychalska M, Watala C: Reduced blood platelet sensitivity to aspirin in coronary artery disease: are dyslipidaemia and inflammatory states possible factors predisposing to sub-optimal platelet response to aspirin? Basic Clin Pharmacol Toxicol. 2006 May;98(5):503-9. Pubmed: 16635110 Link_out
  18. Tantry US, Bliden KP, Gurbel PA: Overestimation of platelet aspirin resistance detection by thrombelastograph platelet mapping and validation by conventional aggregometry using arachidonic acid stimulation. J Am Coll Cardiol. 2005 Nov 1;46(9):1705-9. Epub 2005 Oct 10. Pubmed: 16256872 Link_out
  19. Hermida RC, Ayala DE, Calvo C, Lopez JE, Mojon A, Rodriguez M, Fernandez JR: Differing administration time-dependent effects of aspirin on blood pressure in dipper and non-dipper hypertensives. Hypertension. 2005 Oct;46(4):1060-8. Epub 2005 Aug 8. Pubmed: 16087788 Link_out
  20. Savion N, Varon D: Impact--the cone and plate(let) analyzer: testing platelet function and anti-platelet drug response. Pathophysiol Haemost Thromb. 2006;35(1-2):83-8. Pubmed: 16855351 Link_out
  21. Randomised trial of intravenous streptokinase, oral aspirin, both, or neither among 17,187 cases of suspected acute myocardial infarction: ISIS-2. ISIS-2 (Second International Study of Infarct Survival) Collaborative Group. Lancet. 1988 Aug 13;2(8607):349-60. Pubmed: 2899772 Link_out
  22. Sneader W: The discovery of aspirin: a reappraisal. BMJ. 2000 Dec 23-30;321(7276):1591-4. Pubmed: 11124191 Link_out
  23. Macdonald S: Aspirin use to be banned in under 16 year olds. BMJ. 2002 Nov 2;325(7371):988. Pubmed: 12411346 Link_out
  24. Aukerman G, Knutson D, Miser WF: Management of the acute migraine headache. Am Fam Physician. 2002 Dec 1;66(11):2123-30. Pubmed: 12484694 Link_out
  25. Dorsch MP, Lee JS, Lynch DR, Dunn SP, Rodgers JE, Schwartz T, Colby E, Montague D, Smyth SS: Aspirin resistance in patients with stable coronary artery disease with and without a history of myocardial infarction. Ann Pharmacother. 2007 May;41(5):737-41. Epub 2007 Apr 24. Pubmed: 17456544 Link_out

Enzymes
Name: Aldo-keto reductase family 1 member C1
Reactions: Not Available
Gene Name: AKR1C1
Uniprot ID: Q04828 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prostaglandin G/H synthase 2
Reactions: Not Available
Gene Name: PTGS2
Uniprot ID: P35354 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prostaglandin G/H synthase 1
Reactions: Not Available
Gene Name: PTGS1
Uniprot ID: P23219 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions: Not Available
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C8
Reactions: Not Available
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Multidrug resistance protein 1
Reactions: Not Available
Gene Name: ABCB1
Uniprot ID: P08183 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier family 22 member 6
Reactions: Not Available
Gene Name: SLC22A6
Uniprot ID: Q4U2R8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier family 22 member 7
Reactions: Not Available
Gene Name: SLC22A7
Uniprot ID: Q9Y694 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA