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Showing metabocard for Aminocaproic acid (HMDB0001901)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-03-09 15:02:52 UTC
Update Date2023-02-21 17:15:57 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001901 (Aminocaproic acid)

513
  Mrv1652305271900022D          

  9  8  0  0  0  0            999 V2000
    2.0930    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for HMDB0001901 (Aminocaproic acid)

HMDB0001901
     RDKit          3D
Aminocaproic acid
 22 21  0  0  0  0  0  0  0  0999 V2000
    3.0392    0.7386    0.0900 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633   -0.6464    0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4454   -1.0351   -0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907   -0.1198    0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9792   -0.4258   -0.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529    0.5383    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3234    0.3721   -0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882   -0.4994   -1.0012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3269    1.1829    0.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0820    0.8832    0.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5589    1.3193    0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5374   -1.3225   -0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191   -0.8003    1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803   -2.0869   -0.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5529   -0.9398   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084   -0.3816    1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566    0.9318    0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2064   -1.4699   -0.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9639   -0.3415   -1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5692    1.5781    0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    0.3518    1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3728    2.1729    0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
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3D SDF for HMDB0001901 (Aminocaproic acid)

513
  Mrv1652305271900022D          

  9  8  0  0  0  0            999 V2000
    2.0930    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001901

> <DATABASE_NAME>
hmdb

> <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_KEY>
SLXKOJJOQWFEFD-UHFFFAOYSA-N

> <FORMULA>
C6H13NO2

> <MOLECULAR_WEIGHT>
131.1729

> <EXACT_MASS>
131.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.711240455028708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-aminohexanoic acid

> <ALOGPS_LOGP>
-2.69

> <JCHEM_LOGP>
-1.9971552340836574

> <ALOGPS_LOGS>
-0.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.726140016186165

> <JCHEM_PKA_STRONGEST_BASIC>
10.205507442299444

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
34.6598

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.52e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aminocaproic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001901 (Aminocaproic acid)

HMDB0001901
     RDKit          3D
Aminocaproic acid
 22 21  0  0  0  0  0  0  0  0999 V2000
    3.0392    0.7386    0.0900 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633   -0.6464    0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4454   -1.0351   -0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907   -0.1198    0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9792   -0.4258   -0.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529    0.5383    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3234    0.3721   -0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882   -0.4994   -1.0012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3269    1.1829    0.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0820    0.8832    0.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5589    1.3193    0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5374   -1.3225   -0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191   -0.8003    1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803   -2.0869   -0.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5529   -0.9398   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084   -0.3816    1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566    0.9318    0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2064   -1.4699   -0.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9639   -0.3415   -1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5692    1.5781    0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    0.3518    1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3728    2.1729    0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
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PDB for HMDB0001901 (Aminocaproic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 513                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       3.907   1.155   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.241  -1.155   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      13.243   0.385   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       9.242   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.908   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.576   0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.574   1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.909   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.241   0.385   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    8                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    3    6                                                       
CONECT    9    1    2    7                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0001901 (Aminocaproic acid)

COMPND    HMDB0001901
HETATM    1  N1  UNL     1       3.039   0.739   0.090  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.763  -0.646   0.385  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.445  -1.035  -0.287  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.391  -0.120   0.300  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.979  -0.426  -0.309  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.953   0.538   0.343  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.323   0.372  -0.138  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.588  -0.499  -1.001  1.00  0.00           O  
HETATM    9  O2  UNL     1      -4.327   1.183   0.366  1.00  0.00           O  
HETATM   10  H1  UNL     1       4.082   0.883   0.241  1.00  0.00           H  
HETATM   11  H2  UNL     1       2.559   1.319   0.832  1.00  0.00           H  
HETATM   12  H3  UNL     1       3.537  -1.322  -0.025  1.00  0.00           H  
HETATM   13  H4  UNL     1       2.719  -0.800   1.471  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.180  -2.087  -0.065  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.553  -0.940  -1.372  1.00  0.00           H  
HETATM   16  H7  UNL     1       0.308  -0.382   1.379  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.657   0.932   0.205  1.00  0.00           H  
HETATM   18  H9  UNL     1      -1.206  -1.470  -0.012  1.00  0.00           H  
HETATM   19  H10 UNL     1      -0.964  -0.342  -1.395  1.00  0.00           H  
HETATM   20  H11 UNL     1      -1.569   1.578   0.218  1.00  0.00           H  
HETATM   21  H12 UNL     1      -1.951   0.352   1.438  1.00  0.00           H  
HETATM   22  H13 UNL     1      -4.373   2.173   0.258  1.00  0.00           H  
CONECT    1    2   10   11
CONECT    2    3   12   13
CONECT    3    4   14   15
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    8    9
CONECT    9   22
END
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SMILES for HMDB0001901 (Aminocaproic acid)

NCCCCCC(O)=O
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INCHI for HMDB0001901 (Aminocaproic acid)

InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point205 °CNot Available
Boiling Point255.64 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility505 mg/mL at 25 °CNot Available
LogP-2.95HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
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 QuantifiedNot QuantifiedNot SpecifiedBoth
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00513
Phenol Explorer Compound IDNot Available
FooDB IDFDB022729
KNApSAcK IDC00011195
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
MarkerDB IDNot Available
Good Scents IDrw1212381
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)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: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 ]