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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-03-09 15:02:52 UTC
Update Date2020-04-22 23:33:15 UTC
HMDB IDHMDB0001901
Secondary Accession Numbers
  • HMDB0002002
  • HMDB01901
  • HMDB02002
Metabolite Identification
Common NameAminocaproic acid
DescriptionAminocaproic acid, also known as aminohexanoate or Ahx, 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. Aminocaproic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752215
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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-d2bae6c296c96fbad8d6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9700000000-96516a7056d0134fe91fSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-3900000000-b1e222c28c8ee5ee7e39Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ds-3900000000-d2bae6c296c96fbad8d6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9700000000-96516a7056d0134fe91fSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-3900000000-b1e222c28c8ee5ee7e39Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-329dcaeb92f0ab303d25Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9800000000-f36a0bcbb91fd68401b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-01p9-7900000000-7b0c4a3576914da3beb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-014i-9100000000-6d1cca409e0604efbe03Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0pdi-9000000000-a55855076c25405ac1e5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-a47431cd716ecb19b9e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-1900000000-a5934cb182440e097505Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9100000000-fe8764f31273202c4192Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9000000000-d811796a47319a78c0acSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-85516d2ef8e256aa32c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-b263ad88d0bb4ca9e2a8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-02ta-9400000000-6fd9244fa9d4129efb9fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014i-9000000000-e57b77ac2660e8633c45Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-05ox-9000000000-ac37660729ea0447a3b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-052f-9000000000-dd2777a39a8decd7066dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-02t9-8900000000-024692ea60c820275defSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-a47431cd716ecb19b9e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1900000000-a5934cb182440e097505Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9100000000-fe8764f31273202c4192Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-d811796a47319a78c0acSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-85516d2ef8e256aa32c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ai-4900000000-54865b71f357fde8c392Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9400000000-2873b4030b2888252fdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9000000000-dc3baa186d436fce3845Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-341c4f57265302e0270bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-7900000000-53e66c477bcee7650936Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-fbccc9ade003c2f9aec7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Epidermis
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
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 ]