Showing metabocard for L-Lysine (MMDBc0000059)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:28:53 UTC
Update Date2024-04-30 19:30:58 UTC
Metabolite IDMMDBc0000059
Metabolite Identification
Common NameL-Lysine
DescriptionL-lysine is an essential amino acid. Normal requirements for lysine have been found to be about 8 g per day or 12 mg/kg in adults. Children and infants need more, 44 mg/kg per day for an eleven to-twelve-year old, and 97 mg/kg per day for three-to six-month old. Lysine is highly concentrated in muscle compared to most other amino acids. Lysine is high in foods such as wheat germ, cottage cheese and chicken. Of meat products, wild game and pork have the highest concentration of lysine. Fruits and vegetables contain little lysine, except avocados. Normal lysine metabolism is dependent upon many nutrients including niacin, vitamin B6, riboflavin, vitamin C, glutamic acid and iron. Excess arginine antagonizes lysine. Several inborn errors of lysine metabolism are known, such as cystinuria, hyperdibasic aminoaciduria I, lysinuric protein intolerance, propionic acidemia, and tyrosinemia I. Most are marked by mental retardation with occasional diverse symptoms such as absence of secondary sex characteristics, undescended testes, abnormal facial structure, anemia, obesity, enlarged liver and spleen, and eye muscle imbalance. Lysine also may be a useful adjunct in the treatment of osteoporosis. Although high protein diets result in loss of large amounts of calcium in urine, so does lysine deficiency. Lysine may be an adjunct therapy because it reduces calcium losses in urine. Lysine deficiency also may result in immunodeficiency. Requirements for this amino acid are probably increased by stress. Lysine toxicity has not occurred with oral doses in humans. Lysine dosages are presently too small and may fail to reach the concentrations necessary to prove potential therapeutic applications. Lysine metabolites, amino caproic acid and carnitine have already shown their therapeutic potential. Thirty grams daily of amino caproic acid has been used as an initial daily dose in treating blood clotting disorders, indicating that the proper doses of lysine, its precursor, have yet to be used in medicine. Low lysine levels have been found in patients with Parkinson's, hypothyroidism, kidney disease, asthma and depression. The exact significance of these levels is unclear, yet lysine therapy can normalize the level and has been associated with improvement of some patients with these conditions. Abnormally elevated hydroxylysines have been found in virtually all chronic degenerative diseases and coumadin therapy. The levels of this stress marker may be improved by high doses of vitamin C. Lysine is particularly useful in therapy for marasmus (wasting) and herpes simplex. It stops the growth of herpes simplex in culture, and has helped to reduce the number and occurrence of cold sores in clinical studies. Dosing has not been adequately studied, but beneficial clinical effects occur in doses ranging from 100 mg to 4 g a day. Higher doses may also be useful, and toxicity has not been reported in doses as high as 8 g per day. Diets high in lysine and low in arginine can be useful in the prevention and treatment of herpes. Some researchers think herpes simplex virus is involved in many other diseases related to cranial nerves such as migraines, Bell's palsy and Meniere's disease. Herpes blister fluid will produce fatal encephalitis in the rabbit (http://www.dcnutrition.com).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fd12ea5ad28>


  Mrv1652309272007442D          

 10  9  0  0  0  0            999 V2000
 9998.9803 9997.7078    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.2656 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5517 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8362 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1208 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4074 9998.1199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6950 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4097 9997.7078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6950 9998.9445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9803 9996.8826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fd12ea5ad28>

HMDB0000182
     RDKit          3D
L-Lysine
 24 23  0  0  0  0  0  0  0  0999 V2000
   -4.0460   -0.0933    0.3046 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8810    0.7124   -0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7014   -0.2177   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4089    0.4913   -0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6698   -0.5591   -0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0410   -0.0768   -0.6928 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9656   -1.2094   -0.6151 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999    0.9634    0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9449    2.0890    0.3530 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6177    0.6961    1.0503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7158   -0.7845    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2993   -0.6370   -0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0955    1.1352   -1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7714    1.5098    0.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6229   -0.6562    0.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9099   -1.0396   -0.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169    1.3322    0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447    0.8910   -1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -1.4075   -1.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6666   -0.9934    0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0997    0.2840   -1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5493   -1.9912   -1.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1707   -1.4474    0.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5442    1.0088    0.7357 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  6
  7 22  1  0
  7 23  1  0
 10 24  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fd12ea5ad28>


  Mrv1652309272007442D          

 10  9  0  0  0  0            999 V2000
 9998.9803 9997.7078    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.2656 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5517 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8362 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1208 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4074 9998.1199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6950 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4097 9997.7078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6950 9998.9445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9803 9996.8826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000059

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1

> <INCHI_KEY>
KDXKERNSBIXSRK-YFKPBYRVSA-N

> <FORMULA>
C6H14N2O2

> <MOLECULAR_WEIGHT>
146.1876

> <EXACT_MASS>
146.105527702

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
15.843749178427787

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2,6-diaminohexanoic acid

> <ALOGPS_LOGP>
-3.76

> <JCHEM_LOGP>
-3.2145347205442243

> <ALOGPS_LOGS>
-0.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7382862451337

> <JCHEM_PKA_STRONGEST_BASIC>
10.288061623041543

> <JCHEM_POLAR_SURFACE_AREA>
89.34

> <JCHEM_REFRACTIVITY>
37.8095

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-lysine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fd12ea5ad28>

HMDB0000182
     RDKit          3D
L-Lysine
 24 23  0  0  0  0  0  0  0  0999 V2000
   -4.0460   -0.0933    0.3046 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8810    0.7124   -0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7014   -0.2177   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4089    0.4913   -0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6698   -0.5591   -0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0410   -0.0768   -0.6928 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9656   -1.2094   -0.6151 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999    0.9634    0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9449    2.0890    0.3530 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6177    0.6961    1.0503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7158   -0.7845    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2993   -0.6370   -0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0955    1.1352   -1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7714    1.5098    0.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6229   -0.6562    0.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9099   -1.0396   -0.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169    1.3322    0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447    0.8910   -1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -1.4075   -1.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6666   -0.9934    0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0997    0.2840   -1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5493   -1.9912   -1.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1707   -1.4474    0.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5442    1.0088    0.7357 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  6
  7 22  1  0
  7 23  1  0
 10 24  1  0
M  END
Download

PDB for #<Metabolite:0x00007fd12ea5ad28>

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8664.7638662.388   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.4298663.157   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8662.0968662.388   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8660.7618663.157   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8659.4258662.388   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0    8658.0948663.157   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8666.0978663.157   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8667.4318662.388   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8666.0978664.696   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    8664.7638660.848   0.000  0.00  0.00           N+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    1    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
Download

3D PDB for #<Metabolite:0x00007fd12ea5ad28>

COMPND    HMDB0000182
HETATM    1  N1  UNL     1      -4.046  -0.093   0.305  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.881   0.712  -0.048  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.701  -0.218  -0.049  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.409   0.491  -0.403  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.670  -0.559  -0.362  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.041  -0.077  -0.693  1.00  0.00           C  
HETATM    7  N2  UNL     1       2.966  -1.209  -0.615  1.00  0.00           N  
HETATM    8  C6  UNL     1       2.500   0.963   0.239  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.945   2.089   0.353  1.00  0.00           O  
HETATM   10  O2  UNL     1       3.618   0.696   1.050  1.00  0.00           O  
HETATM   11  H1  UNL     1      -3.716  -0.785   1.015  1.00  0.00           H  
HETATM   12  H2  UNL     1      -4.299  -0.637  -0.568  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.095   1.135  -1.052  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.771   1.510   0.703  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.623  -0.656   0.967  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.910  -1.040  -0.741  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.217   1.332   0.262  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.545   0.891  -1.437  1.00  0.00           H  
HETATM   19  H9  UNL     1       0.444  -1.407  -1.056  1.00  0.00           H  
HETATM   20  H10 UNL     1       0.667  -0.993   0.668  1.00  0.00           H  
HETATM   21  H11 UNL     1       2.100   0.284  -1.739  1.00  0.00           H  
HETATM   22  H12 UNL     1       2.549  -1.991  -1.147  1.00  0.00           H  
HETATM   23  H13 UNL     1       3.171  -1.447   0.360  1.00  0.00           H  
HETATM   24  H14 UNL     1       4.544   1.009   0.736  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3   13   14
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    6    7    8   21
CONECT    7   22   23
CONECT    8    9    9   10
CONECT   10   24
END
Download

SMILES for #<Metabolite:0x00007fd12ea5ad28>

NCCCC[C@H](N)C(O)=O
Download

INCHI for #<Metabolite:0x00007fd12ea5ad28>

InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1
Download
Synonyms
ValueSource
(S)-2,6-Diaminohexanoic acidChEBI
(S)-alpha,epsilon-Diaminocaproic acidChEBI
(S)-LysineChEBI
6-Ammonio-L-norleucineChEBI
KChEBI
L-2,6-Diaminocaproic acidChEBI
L-LysinChEBI
LysChEBI
LysinaChEBI
LysineChEBI
Lysine acidChEBI
LysinumChEBI
2,6-Diaminohexanoic acidKegg
(S)-2,6-DiaminohexanoateGenerator
(S)-a,epsilon-DiaminocaproateGenerator
(S)-a,epsilon-Diaminocaproic acidGenerator
(S)-alpha,epsilon-DiaminocaproateGenerator
(S)-Α,epsilon-diaminocaproateGenerator
(S)-Α,epsilon-diaminocaproic acidGenerator
L-2,6-DiaminocaproateGenerator
2,6-DiaminohexanoateGenerator
(+)-S-LysineHMDB
(S)-2,6-Diamino-hexanoateHMDB
(S)-2,6-Diamino-hexanoic acidHMDB
(S)-a,e-DiaminocaproateHMDB
(S)-a,e-Diaminocaproic acidHMDB
6-Amino-aminutrinHMDB
6-Amino-L-norleucineHMDB
a-LysineHMDB
alpha-LysineHMDB
AminutrinHMDB
H-Lys-OHHMDB
L-(+)-LysineHMDB
L-2,6-DiainohexanoateHMDB
L-2,6-Diainohexanoic acidHMDB
L-LysHMDB
Acetate, lysineHMDB
EnisylHMDB
Lysine hydrochlorideHMDB
L LysineHMDB
Lysine acetateHMDB
Molecular FormulaC6H14N2O2
Average Mass146.1876
Monoisotopic Mass146.105527702
IUPAC Name(2S)-2,6-diaminohexanoic acid
Traditional NameL-lysine
CAS Registry Number56-87-1
SMILES
NCCCC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1
InChI KeyKDXKERNSBIXSRK-YFKPBYRVSA-N