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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-20 22:13:14 UTC
Update Date2020-02-26 21:23:31 UTC
HMDB IDHMDB0001645
Secondary Accession Numbers
  • HMDB01645
Metabolite Identification
Common NameL-Norleucine
DescriptionL-Norleucine, also known as L-aminohexanoate or caprine, 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. Thus, L-norleucine is considered to be a fatty acid lipid molecule. An unnatural amino acid that is used experimentally to study protein structure and function. L-Norleucine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. L-Norleucine exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, L-Norleucine has been detected, but not quantified in, milk (cow). This could make L-norleucine a potential biomarker for the consumption of these foods. It binds reversibly to the kringle domain of plasminogen and blocks the binding of plasminogen to fibrin and its activation to plasmin.
Structure
Data?1582752211
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-hexanoateHMDB
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
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) (2 TMS)splash10-0a4i-0900000000-b9e660e9ed085e0a2756Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0a4i-0900000000-363d31fc4a3b15b97b49Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000i-9200000000-786e1c364f918e406c7fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0900000000-7c99693c3cc849290ecdSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-05fr-8900000000-3cf84aa3585ea0262b9aSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-000i-9200000000-d5ef9dd4b8be3c55a58fSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-0900000000-df2e472e3bd858c871d0Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-0391000000-a01428088011045cef83Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9100000000-1fddf89f6ec7f4b5cfbeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-0910000000-5eb6c8571ebbad86fac9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-b9e660e9ed085e0a2756Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-363d31fc4a3b15b97b49Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9200000000-786e1c364f918e406c7fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05fr-8900000000-3cf84aa3585ea0262b9aSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-0900000000-df2e472e3bd858c871d0Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0391000000-a01428088011045cef83Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9200000000-d5ef9dd4b8be3c55a58fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00bl-9000000000-201d4196a590a77910e6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9400000000-10c311ca7a06deeb972aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9100000000-b124c751376d5dfa51a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ku-9000000000-734efe7e83b2a5a46f00Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-ac9b87f3b366d1310113Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-6cc58ea175a3d1492868Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-95aa6e4bfc4283439983Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-3900000000-b75779678a92cd599f0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0019-9800000000-ee386f888d7ea62be255Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-9000000000-93d53170f5b18b6e157cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00kr-9000000000-8abbc9ef83fc8fdd973cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-39712cf46e67bc1458fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-219a42048a733f3d5a23Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-9000000000-2d321cebc7950b90d6b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00kr-9200000000-916e946734d7c51678dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-bc56a19fa8c09e226543Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-6cc58ea175a3d1492868Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-95aa6e4bfc4283439983Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-3900000000-b75779678a92cd599f0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-bc56a19fa8c09e226543Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001i-0900000000-092c22a76d9d673f6ef9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-9600000000-d20978980da1f4122a43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-e402468856ebe93f5632Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-323f487cfafb31db8c07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-87cdc1a1d627629c2d67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6900000000-7bd938134b1765555ef2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-721ed018b3aaa7a7d07dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Platelet
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified0.0065 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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