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Record Information
Version3.6
Creation Date2005-11-20 22:13:14 UTC
Update Date2016-02-11 01:04:58 UTC
HMDB IDHMDB01645
Secondary Accession NumbersNone
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
Thumb
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
(2S)-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
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 KeyInChIKey=LRQKBLKVPFOOQJ-YFKPBYRVSA-N
Chemical Taxonomy
DescriptionThis compound 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 acyl
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • 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
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.22 m3·mol-1ChemAxon
Polarizability14.46 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) (2 TMS)splash10-0a4i-0900000000-b9e660e9ed085e0a2756View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0a4i-0900000000-363d31fc4a3b15b97b49View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-000i-9200000000-786e1c364f918e406c7fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0a4i-0900000000-7c99693c3cc849290ecdView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-05fr-8900000000-3cf84aa3585ea0262b9aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-000i-9200000000-d5ef9dd4b8be3c55a58fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-0900000000-df2e472e3bd858c871d0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-0391000000-a01428088011045cef83View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9100000000-b124c751376d5dfa51a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ku-9000000000-734efe7e83b2a5a46f00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-ac9b87f3b366d1310113View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-6cc58ea175a3d1492868View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-95aa6e4bfc4283439983View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-3900000000-b75779678a92cd599f0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0019-9800000000-ee386f888d7ea62be255View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9000000000-93d53170f5b18b6e157cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00kr-9000000000-8abbc9ef83fc8fdd973cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-39712cf46e67bc1458fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-219a42048a733f3d5a23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-9000000000-2d321cebc7950b90d6b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00kr-9200000000-916e946734d7c51678dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-bc56a19fa8c09e226543View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Platelet
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified0.0065 umol/mmol creatinineAdult (>18 years old)BothNormal 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 IDFDB022699
KNApSAcK IDNot Available
Chemspider ID19964
KEGG Compound IDC01933
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAminocaproic acid
NuGOwiki LinkHMDB01645
Metagene LinkHMDB01645
METLIN ID6334
PubChem Compound21236
PDB IDNLE
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