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Showing NP-Card for N(6)-Methyllysine (NP0086851)

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Record Information
Version2.0
Created at2022-05-11 16:32:47 UTC
Updated at2022-05-11 16:32:47 UTC
NP-MRD IDNP0086851
Secondary Accession NumbersNone
Natural Product Identification
Common NameN(6)-Methyllysine
DescriptionN(6)-Methyllysine, also known as N-methyl-L-lysine or melys, 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. N(6)-Methyllysine is a very strong basic compound (based on its pKa). N(6)-Methyllysine is found in Apis cerana and Trypanosoma brucei. N(6)-Methyllysine was first documented in 1963 (PMID: 14032673). An L-lysine derivative that is L-lysine in which one of the hydrogens attached to N(6) is substituted by a methyl group (PMID: 15756599).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086851 (N(6)-Methyllysine)


  Mrv0541 02231219202D          

 11 10  0  0  1  0            999 V2000
   13.7124  -11.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4269  -11.2803    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1414  -11.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4269  -10.4553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9980  -11.2803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7124  -12.5178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8559  -11.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5704  -11.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2848  -11.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9993  -11.6928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7138  -11.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  1  0  0  0
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0086851 (N(6)-Methyllysine)

     RDKit          3D

 27 26  0  0  0  0  0  0  0  0999 V2000
    3.5474   -0.9580   -0.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999   -0.1957    0.2224 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6234    0.5144   -0.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8038    1.4001    0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0887    0.6578    1.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8594   -0.3617    0.8489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9271    0.2489   -0.0134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7375    1.1983    0.7306 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039   -0.7931   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0588   -0.7569   -0.3523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -1.8243   -1.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6696   -1.9667   -0.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -0.4211   -0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3487   -0.9395   -1.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1136   -0.8816    0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0699    1.1050   -1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385   -0.2206   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0953    1.9667   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4634    2.1943    0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8321    0.1299    2.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4293    1.3719    2.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3496   -0.8431    1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719   -1.1261    0.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806    0.8041   -0.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8633    0.8037    1.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6725    1.2399    0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9623   -2.3466   -1.9230 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  1  0
  7  9  1  0
  9 11  1  0
  9 10  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
 11 27  1  0
M  END
Download

3D SDF for NP0086851 (N(6)-Methyllysine)


  Mrv0541 02231219202D          

 11 10  0  0  1  0            999 V2000
   13.7124  -11.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4269  -11.2803    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1414  -11.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4269  -10.4553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9980  -11.2803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7124  -12.5178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8559  -11.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5704  -11.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2848  -11.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9993  -11.6928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7138  -11.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  1  0  0  0
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086851

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNCCCC[C@H](N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H16N2O2/c1-9-5-3-2-4-6(8)7(10)11/h6,9H,2-5,8H2,1H3,(H,10,11)/t6-/m0/s1

> <INCHI_KEY>
PQNASZJZHFPQLE-LURJTMIESA-N

> <FORMULA>
C7H16N2O2

> <MOLECULAR_WEIGHT>
160.2141

> <EXACT_MASS>
160.121177766

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
18.03722192401942

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-6-(methylamino)hexanoic acid

> <ALOGPS_LOGP>
-2.37

> <JCHEM_LOGP>
-2.9121419829334894

> <ALOGPS_LOGS>
-0.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7952434302703955

> <JCHEM_PKA_STRONGEST_BASIC>
10.584347443918325

> <JCHEM_POLAR_SURFACE_AREA>
75.35000000000001

> <JCHEM_REFRACTIVITY>
42.5841

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-methyl-L-lysine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0086851 (N(6)-Methyllysine)

Download
PDB for NP0086851 (N(6)-Methyllysine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      25.596 -21.827   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.930 -21.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.264 -21.827   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      26.930 -19.517   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0      24.263 -21.057   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      25.596 -23.367   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      29.598 -21.057   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.931 -21.827   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.265 -21.057   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      33.599 -21.827   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      34.932 -21.057   0.000  0.00  0.00           C+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2    7                                                       
CONECT    4    2                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

Download
3D PDB for NP0086851 (N(6)-Methyllysine)
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SMILES for NP0086851 (N(6)-Methyllysine)
CNCCCC[C@H](N)C(O)=O
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INCHI for NP0086851 (N(6)-Methyllysine)
InChI=1S/C7H16N2O2/c1-9-5-3-2-4-6(8)7(10)11/h6,9H,2-5,8H2,1H3,(H,10,11)/t6-/m0/s1
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View in JSmol
Synonyms
ValueSource
(S)-2-Amino-6-methylaminohexanoic acidChEBI
epsilon-MethyllysineChEBI
Epsilon-N-MethyllysineChEBI
MeLysChEBI
N(zeta)-MethyllysineChEBI
N-Epsilon-MethyllysineChEBI
N-Methyl-L-lysineChEBI
N6-Methyl-L-lysineChEBI
N(epsilon)-Methyl-L-lysineChEBI
(S)-2-Amino-6-methylaminohexanoateGenerator
N(Z)-MethyllysineGenerator
N(Ζ)-methyllysineGenerator
(2S)-2-Amino-6-(methylamino)hexanoateHMDB
(2S)-2-Amino-6-(methylamino)hexanoic acidHMDB
N(6)-Methyl-L-lysineHMDB
N-Methyl-lysineHMDB
epsilon-N-Methyllysine hydrochloride, (L-lys)-isomerHMDB
epsilon-N-Methyllysine, (DL-lys)-isomerHMDB
N(epsilon)-Monomethyl-lysineHMDB
N(6)-MethyllysineChEBI
Chemical FormulaC7H16N2O2
Average Mass160.2141 Da
Monoisotopic Mass160.12118 Da
IUPAC Name(2S)-2-amino-6-(methylamino)hexanoic acid
Traditional NameN-methyl-L-lysine
CAS Registry NumberNot Available
SMILES
CNCCCC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C7H16N2O2/c1-9-5-3-2-4-6(8)7(10)11/h6,9H,2-5,8H2,1H3,(H,10,11)/t6-/m0/s1
InChI KeyPQNASZJZHFPQLE-LURJTMIESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
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
    • 

  • Carboxylic acid
    • 

  • Secondary aliphatic amine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Secondary amine
    • 

  • Carbonyl group
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.4ALOGPS
logP-2.9ChemAxon
logS-0.49ALOGPS
pKa (Strongest Acidic)2.8ChemAxon
pKa (Strongest Basic)10.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area75.35 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.58 m³·mol⁻¹ChemAxon
Polarizability18.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002038  
DrugBank IDDB01714  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022812  
KNApSAcK IDNot Available
Chemspider ID144469  
KEGG Compound IDC02728  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound164795  
PDB IDNot Available
ChEBI ID17604  
Good Scents IDNot Available
References
General References
  1. Kalasz H, Klebovich I, Balogh-Nemes K, Szilagyi A, Tihanyi M, Szarvas T, Lengyel J: Detection of N-monomethyl-lysine generated by metabolic transmethylation. Anal Bioanal Chem. 2005 Jun;382(3):760-4. doi: 10.1007/s00216-005-3089-4. Epub 2005 Mar 9. [PubMed:15756599  ] 
  2. KIM S, BENOITON L, PAIK WK: On the metabolism of epsilon-N-methyl-L-lysine by rat-kidney homogenate. Biochim Biophys Acta. 1963 Jun 4;71:745-7. doi: 10.1016/0006-3002(63)91156-9. [PubMed:14032673  ]