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Human Metabolome Database Version 2.5

 

Showing metabocard for Aminocaproic acid (HMDB01901)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-03-09 15:02:52
Update Date 2009-05-05 20:58:56
Accession Number HMDB01901
Secondary Accession Numbers HMDB02002
Common Name Aminocaproic acid
Description Aminocaproic acid (marketed as Amicar) is a drug used to treat bleeding disorders. It is an antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties. It is a derivative of the amino acid lysine. It binds reversibly to the kringle domain of plasminogen and blocks the binding of plasminogen to fibrin and its activation to plasmin.
Synonyms
  1. 6-Amino-n-hexanoic acid
  2. 6-Aminocaproic acid
  3. 6-Aminohexanoate
  4. 6-amino-Hexanoic acid
  5. 6-aminohexanoic acid
  6. Acepramin
  7. Acepramine
  8. Acikaprin
  9. Afibrin
  10. Amicar
  11. Amikar
  12. Aminokapron
  13. Atsemin
  14. Caplamin
  15. Capracid
  16. Capramol
  17. Capranol
  18. Caprocid
  19. Caprolisin
  20. Epsamon
  21. Epsicapron
  22. Epsikapron
  23. Epsillon-Aminocaproic acid' Epsilcapramin
  24. Epsilcapramine
  25. Epsilon S
  26. H-6-Ahx-OH
  27. H-EAhx-OH
  28. H-epsilon-Acp-OH
  29. Hemocaprol
  30. Hemopar
  31. Hepin
  32. Ipsilon
  33. Respramin
  34. e-Amino-n-hexanoic acid
  35. e-Aminocaproate
  36. e-Aminocaproic acid USP
  37. e-Aminohexanoic acid
  38. e-Leucine
  39. e-Norleucine
  40. epsilon-Aminocaproic acid
  41. epsilon-Norleucine
  42. epsilon-S
  43. omega-Aminocaproic acid
  44. omega-Aminohexanoic acid
  45. w-Aminocaproic acid
  46. w-Aminohexanoic acid
  47. epsilon-Amino-n-hexanoic acid
  48. epsilon-Aminocaproate
  49. epsilon-Aminocaproic acid USP
  50. epsilon-Aminohexanoic acid
  51. epsilon-Leucine
  52. 6-Amino-n-hexanoate
  53. 6-Aminocaproate
  54. 6-amino-Hexanoate
  55. Epsillon-Aminocaproate
  56. e-Amino-n-hexanoate
  57. e-Aminocaproic acid
  58. e-Aminohexanoate
  59. omega-Aminocaproate
  60. omega-Aminohexanoate
  61. w-Aminocaproate
  62. w-Aminohexanoate
  63. epsilon-Amino-n-hexanoate
  64. epsilon-Aminohexanoate
  65. Epsillon-Aminocaproic acid
Chemical IUPAC Name 6-aminohexanoic acid
Chemical Formula C6H13NO2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian Metabolite
Species
  • primary amine
  • primary aliphatic amine (alkylamine)
  • carboxylic acid
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application
—
Source
  • Exogenous
Average Molecular Weight 131.173
Monoisotopic Molecular Weight 131.094635
Isomeric SMILES NCCCCCC(O)=O
Canonical SMILES NCCCCCC(O)=O
KEGG Compound ID C02378 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Amicar Link Image
NuGOwiki Link HMDB01901 Link Image
Metagene Link HMDB01901 Link Image
METLIN ID Not Available
PubChem Compound 564 Link Image
PubChem Substance 5420 Link Image
ChEBI ID 16586 Link Image
CAS Registry Number 60-32-2
InChI Identifier InChI=1/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
Synthesis Reference Not Available
Melting Point (Experimental) 205 oC
Experimental Water Solubility 505.0 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 45.2 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity -2.95 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity -2.69 [Predicted by ALOGPS]; 0 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location
  • Blood
Tissue Location
Tissue References
Skin —
Concentrations (Normal)
Biofluid Blood
Value 2.0 (0.76-3.05) uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Wu AHB (2006) Tietz clinical guide to laboratory tests, 4th ed. WB Saunders, St. Louis.
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways Not Available
General References
  1. Van Hoeyveld EM, Stevens EA: Stabilizing effect of epsilon-aminocaproic acid on allergenic extracts. J Allergy Clin Immunol. 1985 Oct;76(4):543-50. [PubMed Link Image]
  2. Kim CS, Lee CH, Chung JW, Kim CD: Interleukin-1 alpha, interleukin-1 beta and interleukin-8 gene expression in human aural cholesteatomas. Acta Otolaryngol. 1996 Mar;116(2):302-6. [PubMed Link Image]
  3. Wikipedia Link Image