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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-03-09 15:02:52 UTC
Update Date2019-07-23 05:45:09 UTC
HMDB IDHMDB0001901
Secondary Accession Numbers
  • HMDB0002002
  • HMDB01901
  • 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
Data?1563860709
Synonyms
ValueSource
6-Aminocaproic acidChEBI
Acide aminocaproqueChEBI
Acido aminocaproicoChEBI
Acidum aminocaproicumChEBI
AhxChEBI
AmicarChEBI
AmikarChEBI
AMINOCAPROICChEBI
Aminohexanoic acidChEBI
CapralenseChEBI
CapramolChEBI
CaproaminChEBI
CaprocidChEBI
CaprolisinChEBI
EACAChEBI
EpsamonChEBI
EpsicapromChEBI
EpsicapronChEBI
EpsikapronChEBI
EpsilcapraminChEBI
EpsilcapramineChEBI
Epsilon SChEBI
epsilon-AhxChEBI
epsilon-Amino-N-hexanoic acidChEBI
epsilon-Aminocaproic acidChEBI
epsilon-Aminohexanoic acidChEBI
epsilon-LeucineChEBI
epsilon-NorleucineChEBI
Omega-aminocaproic acidChEBI
Omega-aminohexanoic acidChEBI
RespraminChEBI
ZChEBI
6-Aminohexanoic acidKegg
6-AminocaproateGenerator
AminohexanoateGenerator
epsilon-Amino-N-hexanoateGenerator
epsilon-AminocaproateGenerator
epsilon-AminohexanoateGenerator
Omega-aminocaproateGenerator
Omega-aminohexanoateGenerator
6-AminohexanoateGenerator
AminocaproateGenerator
6-Amino-hexanoateHMDB
6-Amino-hexanoic acidHMDB
6-Amino-N-hexanoateHMDB
6-Amino-N-hexanoic acidHMDB
AcepraminHMDB
AcepramineHMDB
AcikaprinHMDB
AfibrinHMDB
AminokapronHMDB
AtseminHMDB
CaplaminHMDB
CapracidHMDB
CapranolHMDB
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
Epsillon-aminocaproateHMDB
Epsillon-aminocaproic acidHMDB
Epsillon-aminocaproic acid' epsilcapraminHMDB
epsilon-Aminocaproic acid uspHMDB
epsilon-SHMDB
H-6-Ahx-OHHMDB
H-EAhx-OHHMDB
H-epsilon-Acp-OHHMDB
HemocaprolHMDB
HemoparHMDB
HepinHMDB
IpsilonHMDB
W-AminocaproateHMDB
W-Aminocaproic acidHMDB
W-AminohexanoateHMDB
W-Aminohexanoic acidHMDB
Pharmachemie brand OF aminocaproic acidHMDB
Delagrange brand OF aminocaproic acidHMDB
HexalenseHMDB
epsilon Aminocaproic acidHMDB
6 Aminocaproic acidHMDB
Leurquin brand OF aminocaproic acidHMDB
Rottapharm brand OF aminocaproic acidHMDB
6 Aminohexanoic acidHMDB
CaprolestHMDB
Sanofi winthrop brand OF aminocaproic 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 KeySLXKOJJOQWFEFD-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point205 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility505 mg/mL at 25 °CNot Available
LogP-2.95HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility45.2 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.66 m³·mol⁻¹ChemAxon
Polarizability14.71 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00ds-3900000000-d2bae6c296c96fbad8d6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9700000000-96516a7056d0134fe91fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-3900000000-b1e222c28c8ee5ee7e39JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ds-3900000000-d2bae6c296c96fbad8d6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9700000000-96516a7056d0134fe91fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-3900000000-b1e222c28c8ee5ee7e39JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-329dcaeb92f0ab303d25JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9800000000-f36a0bcbb91fd68401b1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-01p9-7900000000-7b0c4a3576914da3beb0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-014i-9100000000-6d1cca409e0604efbe03JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0pdi-9000000000-a55855076c25405ac1e5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-a47431cd716ecb19b9e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-1900000000-a5934cb182440e097505JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9100000000-fe8764f31273202c4192JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9000000000-d811796a47319a78c0acJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-85516d2ef8e256aa32c4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-b263ad88d0bb4ca9e2a8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-02ta-9400000000-6fd9244fa9d4129efb9fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014i-9000000000-e57b77ac2660e8633c45JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-05ox-9000000000-ac37660729ea0447a3b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-052f-9000000000-dd2777a39a8decd7066dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-02t9-8900000000-024692ea60c820275defJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-a47431cd716ecb19b9e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1900000000-a5934cb182440e097505JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9100000000-fe8764f31273202c4192JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-d811796a47319a78c0acJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-85516d2ef8e256aa32c4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ai-4900000000-54865b71f357fde8c392JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9400000000-2873b4030b2888252fdbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9000000000-dc3baa186d436fce3845JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-341c4f57265302e0270bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-7900000000-53e66c477bcee7650936JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-fbccc9ade003c2f9aec7JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Skin
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (0.76-3.05) uMAdult (>18 years old)BothNormal
    • Wu AHB (2006) Tie...
details
FecesDetected but not Quantified Not SpecifiedBoth
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00513
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022729
KNApSAcK IDNot Available
Chemspider ID548
KEGG Compound IDC02378
BioCyc IDCPD-884
BiGG IDNot Available
Wikipedia LinkAminocaproic_acid
METLIN IDNot Available
PubChem Compound564
PDB IDNot Available
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. [PubMed: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. [PubMed:8725537 ]