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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-20 22:13:14 UTC
Update Date2019-07-23 05:45:06 UTC
HMDB IDHMDB0001645
Secondary Accession Numbers
  • HMDB01645
Metabolite Identification
Common NameL-Norleucine
DescriptionL-Norleucine is an unnatural amino acid that is used experimentally to study protein structure and function. It is structurally similar to methionine, however it does not contain sulfur. Aminocaproic acid works as an antifibrinolytic. 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?1563860706
Synonyms
ValueSource
(S)-2-Aminohexanoic acidChEBI
2-Aminocaproic acidChEBI
2-Aminohexanoic acidChEBI
alpha-Aminocaproic acidChEBI
CaprineChEBI
GlycoleucineChEBI
L(+)-NorleucineChEBI
L-(+)-NorleucineChEBI
L-2-AminohexanoateChEBI
L-2-Aminohexanoic acidChEBI
L-AminohexanoateChEBI
L-Aminohexanoic acidChEBI
NleChEBI
NorleucineChEBI
(S)-2-AminohexanoateGenerator
2-AminocaproateGenerator
2-AminohexanoateGenerator
a-AminocaproateGenerator
a-Aminocaproic acidGenerator
alpha-AminocaproateGenerator
Α-aminocaproateGenerator
Α-aminocaproic acidGenerator
(S)-2-Amino-hexanoateHMDB
(S)-2-Amino-hexanoic acidHMDB
(S)-AminohexanoateHMDB
(S)-Aminohexanoic acidHMDB
(S)-NorleucineHMDB
L-Isomer norleucineHMDB
Norleucine, L isomerHMDB
Norleucine, L-isomerHMDB
2S-Amino-hexanoateGenerator
Chemical FormulaC6H13NO2
Average Molecular Weight131.1729
Monoisotopic Molecular Weight131.094628665
IUPAC Name(2S)-2-aminohexanoic acid
Traditional Namecaprine
CAS Registry Number327-57-1
SMILES
CCCC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1
InChI KeyLRQKBLKVPFOOQJ-YFKPBYRVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility12 mg/mL at 25 °CNot Available
LogP-1.53HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility89.1 g/LALOGPS
logP-1.7ALOGPS
logP-1.4ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.22 m³·mol⁻¹ChemAxon
Polarizability14.46 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) (2 TMS)splash10-0a4i-0900000000-b9e660e9ed085e0a2756JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0a4i-0900000000-363d31fc4a3b15b97b49JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000i-9200000000-786e1c364f918e406c7fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0900000000-7c99693c3cc849290ecdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-05fr-8900000000-3cf84aa3585ea0262b9aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-000i-9200000000-d5ef9dd4b8be3c55a58fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-0900000000-df2e472e3bd858c871d0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-0391000000-a01428088011045cef83JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9100000000-1fddf89f6ec7f4b5cfbeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-0910000000-5eb6c8571ebbad86fac9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-b9e660e9ed085e0a2756JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-363d31fc4a3b15b97b49JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9200000000-786e1c364f918e406c7fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05fr-8900000000-3cf84aa3585ea0262b9aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-0900000000-df2e472e3bd858c871d0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0391000000-a01428088011045cef83JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9200000000-d5ef9dd4b8be3c55a58fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00bl-9000000000-201d4196a590a77910e6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9400000000-10c311ca7a06deeb972aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9100000000-b124c751376d5dfa51a5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ku-9000000000-734efe7e83b2a5a46f00JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-ac9b87f3b366d1310113JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-6cc58ea175a3d1492868JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-95aa6e4bfc4283439983JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-3900000000-b75779678a92cd599f0cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0019-9800000000-ee386f888d7ea62be255JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9000000000-93d53170f5b18b6e157cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00kr-9000000000-8abbc9ef83fc8fdd973cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-39712cf46e67bc1458fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-219a42048a733f3d5a23JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-9000000000-2d321cebc7950b90d6b1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00kr-9200000000-916e946734d7c51678dfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-bc56a19fa8c09e226543JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-6cc58ea175a3d1492868JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-95aa6e4bfc4283439983JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-3900000000-b75779678a92cd599f0cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-bc56a19fa8c09e226543JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-092c22a76d9d673f6ef9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-9600000000-d20978980da1f4122a43JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-e402468856ebe93f5632JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-323f487cfafb31db8c07JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-87cdc1a1d627629c2d67JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6900000000-7bd938134b1765555ef2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-721ed018b3aaa7a7d07dJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Platelet
  • Testes
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.0065 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022699
    KNApSAcK IDNot Available
    Chemspider ID19964
    KEGG Compound IDC01933
    BioCyc IDL-2-AMINOHEXANOATE
    BiGG IDNot Available
    Wikipedia LinkNorleucine
    METLIN ID6334
    PubChem Compound21236
    PDB IDNot Available
    ChEBI ID18347
    References
    Synthesis ReferenceChibata, Ichiro; Kizumi, Masahiko; Sugiura, Masataka. Fermentative production of L-norleucine. Jpn. Kokai Tokkyo Koho (1977), 4 pp.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General ReferencesNot Available