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Record Information
Version3.6
Creation Date2006-03-09 15:02:52 UTC
Update Date2016-02-11 01:05:05 UTC
HMDB IDHMDB01901
Secondary Accession Numbers
  • HMDB02002
Metabolite Identification
Common NameAminocaproic acid
DescriptionAminocaproic 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.
Structure
Thumb
Synonyms
ValueSource
6-Aminocaproic acidChEBI
Acide aminocaproqueChEBI
acido AminocaproicoChEBI
Acidum aminocaproicumChEBI
AhxChEBI
AMICARChEBI
AMINOCAPROICChEBI
Aminocaproic acidChEBI
Aminohexanoic acidChEBI
CaproaminChEBI
EACAChEBI
EpsicapromChEBI
EpsilcapramineChEBI
epsilon-AhxChEBI
epsilon-Aminohexanoic acidChEBI
ZChEBI
6-AminocaproateGenerator
epsilon-AminocaproateGenerator
AminocaproateGenerator
AminohexanoateGenerator
epsilon-AminohexanoateGenerator
6-amino-HexanoateHMDB
6-amino-Hexanoic acidHMDB
6-amino-N-HexanoateHMDB
6-amino-N-Hexanoic acidHMDB
6-AminohexanoateHMDB
6-Aminohexanoic acidHMDB
AcepraminHMDB
AcepramineHMDB
AcikaprinHMDB
AfibrinHMDB
AmikarHMDB
AminokapronHMDB
AtseminHMDB
CaplaminHMDB
CapracidHMDB
CapramolHMDB
CapranolHMDB
CaprocidHMDB
CaprolisinHMDB
e-amino-N-HexanoateHMDB
e-amino-N-Hexanoic acidHMDB
e-AminocaproateHMDB
e-Aminocaproic acidHMDB
e-Aminocaproic acid uspHMDB
e-AminohexanoateHMDB
e-Aminohexanoic acidHMDB
e-LeucineHMDB
e-NorleucineHMDB
EpsamonHMDB
EpsicapronHMDB
EpsikapronHMDB
Epsillon-aminocaproateHMDB
Epsillon-aminocaproic acidHMDB
Epsillon-aminocaproic acid' epsilcapraminHMDB
epsilon SHMDB
epsilon-amino-N-HexanoateHMDB
epsilon-amino-N-Hexanoic acidHMDB
epsilon-Aminocaproic acid uspHMDB
epsilon-LeucineHMDB
epsilon-NorleucineHMDB
epsilon-SHMDB
H-6-Ahx-OHHMDB
H-EAhx-OHHMDB
H-epsilon-Acp-OHHMDB
HemocaprolHMDB
HemoparHMDB
HepinHMDB
IpsilonHMDB
Omega-aminocaproateHMDB
Omega-aminocaproic acidHMDB
Omega-aminohexanoateHMDB
Omega-aminohexanoic acidHMDB
RespraminHMDB
W-AminocaproateHMDB
W-Aminocaproic acidHMDB
W-AminohexanoateHMDB
W-Aminohexanoic acidHMDB
Chemical FormulaC6H13NO2
Average Molecular Weight131.1729
Monoisotopic Molecular Weight131.094628665
IUPAC Name6-aminohexanoic acid
Traditional Nameaminocaproic acid
CAS Registry Number60-32-2
SMILES
NCCCCCC(O)=O
InChI Identifier
InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
InChI KeyInChIKey=SLXKOJJOQWFEFD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Amino fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Protein synthesis, amino acid biosynthesis
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point205 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility505.0 mg/mL at 25 °CNot Available
LogP-2.95HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility45.2 mg/mLALOGPS
logP-2.7ALOGPS
logP-2ChemAxon
logS-0.46ALOGPS
pKa (Strongest Acidic)4.73ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.66 m3·mol-1ChemAxon
Polarizability14.71 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00ds-3900000000-d2bae6c296c96fbad8d6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9700000000-96516a7056d0134fe91fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-3900000000-b1e222c28c8ee5ee7e39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-01p9-7900000000-7b0c4a3576914da3beb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-014i-9100000000-6d1cca409e0604efbe03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0pdi-9000000000-a55855076c25405ac1e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-a47431cd716ecb19b9e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-1900000000-a5934cb182440e097505View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9100000000-fe8764f31273202c4192View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9000000000-d811796a47319a78c0acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-85516d2ef8e256aa32c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-b263ad88d0bb4ca9e2a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-02ta-9400000000-6fd9244fa9d4129efb9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014i-9000000000-e57b77ac2660e8633c45View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-05ox-9000000000-ac37660729ea0447a3b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-052f-9000000000-dd2777a39a8decd7066dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-02t9-8900000000-024692ea60c820275defView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • Skin
Pathways
NameSMPDB LinkKEGG Link
Aminocaproic Acid PathwaySMP00286Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (0.76-3.05) uMAdult (>18 years old)BothNormal
    • Wu AHB (2006) Tie...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022729
KNApSAcK IDNot Available
Chemspider ID548
KEGG Compound IDC02378
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmicar
NuGOwiki LinkHMDB01901
Metagene LinkHMDB01901
METLIN IDNot Available
PubChem Compound564
PDB IDACA
ChEBI ID16586
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [4056242 ]
  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. [8725537 ]