MiMeDB: Showing metabocard for Saccharopine (MMDBc0000510)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:39:24 UTC

Update Date

2024-04-30 19:32:43 UTC

Metabolite ID

MMDBc0000510

Metabolite Identification

Common Name

Saccharopine

Description

Saccharopine is an intermediate in the degradation of lysine, formed by the condensation of lysine and alpha-ketoglutarate. The saccharopine pathway is the main route for lysine degradation in mammals, and its first two reactions are catalyzed by enzymatic activities known as lysine-oxoglutarate reductase (LOR) and saccharopine dehydrogenase (SDH), which reside on a single bifunctional polypeptide (LOR/SDH) (EC 1.5.1.8). The reactions involved with saccharopine dehydrogenases have very strict substrate specificity for L-lysine, 2-oxoglutarate, and NADPH. LOR/SDH has been detected in a number of mammalian tissues, mainly in the liver and kidney, contributing not only to the general nitrogen balance in the organism but also to the controlled conversion of lysine into ketone bodies. A tetrameric form has also been observed in human liver and placenta. LOR activity has also been detected in brain mitochondria during embryonic development, and this opens up the question of whether or not lysine degradation has any functional significance during brain development. As a result, there is now a new focus on the nutritional requirements for lysine in gestation and infancy. Finally, LOR and/or SDH deficiencies seem to be involved in a human autosomal genetic disorder known as familial hyperlysinemia, which is characterized by serious defects in the functioning of the nervous system and characterized by a deficiency in lysine-ketoglutarate reductase, saccharopine dehydrogenase, and saccharopine oxidoreductase activities. Saccharopinuria (high amounts of saccharopine in the urine) and saccharopinemia (an excess of saccharopine in the blood) are conditions present in some inherited disorders of lysine degradation (PMID: 463877 , 10567240 , 10772957 , 4809305 ). If present in sufficiently high levels, saccharopine can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Saccharopine is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). Many affected children with organic acidemias experience intellectual disability or delayed development.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000279
     RDKit          3D
Saccharopine
 39 38  0  0  0  0  0  0  0  0999 V2000
   -4.2431    0.6793   -0.9565 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0850   -0.4854   -0.0994 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2506   -0.1163    1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    0.3755    0.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1627   -0.7054   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2366   -0.3090   -0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    0.0188    0.6578 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4078    0.4160    0.2516 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1025   -0.6496   -0.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5014   -0.2917   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3694   -0.0549    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3377    1.0090    0.8965 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2573   -1.0393    0.7199 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4093    1.6983   -0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763    2.3087   -0.5473 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4659    2.3388   -1.0445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4111   -0.9346    0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4994   -1.9165    1.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5313   -0.2446    0.0379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1532    1.1494   -0.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2920    0.3515   -1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6729   -1.3292   -0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8229    0.6293    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1570   -1.0500    1.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967    1.2983    0.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3656    0.6306    1.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7233   -0.8533   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1430   -1.6279    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580   -1.2697   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128    0.4707   -1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6890    0.8355    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151    0.6001    1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -1.6042    0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5681   -0.8730   -1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5772    0.4794   -1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460   -1.2153   -1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0307   -2.0368    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1116    2.9655   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0593    0.3519    0.6454 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 14 16  1  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  1
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 13 37  1  0
 16 38  1  0
 19 39  1  0
M  END


  Mrv1652309032023592D          

 19 18  0  0  0  0            999 V2000
10001.123310002.5437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.408510002.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.693910002.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.979210002.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.264610002.5437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.979210003.7807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.837910002.9560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.552410002.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.266810002.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.984310002.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.697710002.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.413110002.5437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10006.128510002.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.841910002.5437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.128510003.7807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.413110001.7194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.123310001.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.408510001.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.837910001.3058    0.0000 O   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 17  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000510

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1

> <INCHI_KEY>
ZDGJAHTZVHVLOT-YUMQZZPRSA-N

> <FORMULA>
C11H20N2O6

> <MOLECULAR_WEIGHT>
276.2863

> <EXACT_MASS>
276.132136382

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.138708375547512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid

> <ALOGPS_LOGP>
-2.77

> <JCHEM_LOGP>
-5.407435330625966

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.375174811126724

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4444535649435268

> <JCHEM_PKA_STRONGEST_BASIC>
10.892138404544818

> <JCHEM_POLAR_SURFACE_AREA>
149.95

> <JCHEM_REFRACTIVITY>
63.95300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
saccharopine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000279
     RDKit          3D
Saccharopine
 39 38  0  0  0  0  0  0  0  0999 V2000
   -4.2431    0.6793   -0.9565 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0850   -0.4854   -0.0994 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2506   -0.1163    1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    0.3755    0.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1627   -0.7054   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2366   -0.3090   -0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    0.0188    0.6578 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4078    0.4160    0.2516 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1025   -0.6496   -0.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5014   -0.2917   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3694   -0.0549    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3377    1.0090    0.8965 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2573   -1.0393    0.7199 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4093    1.6983   -0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763    2.3087   -0.5473 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4659    2.3388   -1.0445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4111   -0.9346    0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4994   -1.9165    1.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5313   -0.2446    0.0379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1532    1.1494   -0.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2920    0.3515   -1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6729   -1.3292   -0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8229    0.6293    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1570   -1.0500    1.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967    1.2983    0.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3656    0.6306    1.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7233   -0.8533   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1430   -1.6279    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580   -1.2697   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128    0.4707   -1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6890    0.8355    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151    0.6001    1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -1.6042    0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5681   -0.8730   -1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5772    0.4794   -1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460   -1.2153   -1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0307   -2.0368    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1116    2.9655   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0593    0.3519    0.6454 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 14 16  1  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  1
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 13 37  1  0
 16 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.7638671.415   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.4298672.185   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8666.0958671.415   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.7618672.185   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8663.4278671.415   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8664.7618673.724   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8670.0978672.185   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8671.4318671.415   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8672.7658672.185   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8674.1048671.415   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8675.4368672.185   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8676.7718671.415   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8678.1078672.185   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8679.4388671.415   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8678.1078673.724   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0    8676.7718669.876   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0    8668.7638669.876   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8667.4298669.104   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    8670.0978669.104   0.000  0.00  0.00           O+0
CONECT    1    2    7   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12                                                            
CONECT   17    1   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0000279
HETATM    1  N1  UNL     1      -4.243   0.679  -0.956  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.085  -0.485  -0.099  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.251  -0.116   1.105  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.871   0.376   0.727  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.163  -0.705  -0.015  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.237  -0.309  -0.441  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.071   0.019   0.658  1.00  0.00           N  
HETATM    8  C6  UNL     1       2.408   0.416   0.252  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.102  -0.650  -0.508  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.501  -0.292  -0.896  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.369  -0.055   0.277  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.338   1.009   0.896  1.00  0.00           O  
HETATM   13  O2  UNL     1       6.257  -1.039   0.720  1.00  0.00           O  
HETATM   14  C10 UNL     1       2.409   1.698  -0.458  1.00  0.00           C  
HETATM   15  O3  UNL     1       1.276   2.309  -0.547  1.00  0.00           O  
HETATM   16  O4  UNL     1       3.466   2.339  -1.045  1.00  0.00           O  
HETATM   17  C11 UNL     1      -5.411  -0.935   0.412  1.00  0.00           C  
HETATM   18  O5  UNL     1      -5.499  -1.916   1.163  1.00  0.00           O  
HETATM   19  O6  UNL     1      -6.531  -0.245   0.038  1.00  0.00           O  
HETATM   20  H1  UNL     1      -5.153   1.149  -0.728  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.292   0.351  -1.937  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.673  -1.329  -0.679  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.823   0.629   1.689  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.157  -1.050   1.716  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.997   1.298   0.130  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.366   0.631   1.691  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.723  -0.853  -0.984  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.143  -1.628   0.559  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.658  -1.270  -0.880  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.213   0.471  -1.193  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.689   0.836   1.221  1.00  0.00           H  
HETATM   32  H13 UNL     1       3.015   0.600   1.197  1.00  0.00           H  
HETATM   33  H14 UNL     1       3.197  -1.604   0.092  1.00  0.00           H  
HETATM   34  H15 UNL     1       2.568  -0.873  -1.474  1.00  0.00           H  
HETATM   35  H16 UNL     1       4.577   0.479  -1.685  1.00  0.00           H  
HETATM   36  H17 UNL     1       4.946  -1.215  -1.404  1.00  0.00           H  
HETATM   37  H18 UNL     1       6.031  -2.037   0.631  1.00  0.00           H  
HETATM   38  H19 UNL     1       4.112   2.966  -0.630  1.00  0.00           H  
HETATM   39  H20 UNL     1      -7.059   0.352   0.645  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3   17   22
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   31
CONECT    8    9   14   32
CONECT    9   10   33   34
CONECT   10   11   35   36
CONECT   11   12   12   13
CONECT   13   37
CONECT   14   15   15   16
CONECT   16   38
CONECT   17   18   18   19
CONECT   19   39
END

HMDB0000279
     RDKit          3D
Saccharopine
 39 38  0  0  0  0  0  0  0  0999 V2000
   -4.2431    0.6793   -0.9565 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0850   -0.4854   -0.0994 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2506   -0.1163    1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    0.3755    0.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1627   -0.7054   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2366   -0.3090   -0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    0.0188    0.6578 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4078    0.4160    0.2516 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1025   -0.6496   -0.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5014   -0.2917   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3694   -0.0549    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3377    1.0090    0.8965 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2573   -1.0393    0.7199 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4093    1.6983   -0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763    2.3087   -0.5473 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4659    2.3388   -1.0445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4111   -0.9346    0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4994   -1.9165    1.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5313   -0.2446    0.0379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1532    1.1494   -0.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2920    0.3515   -1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6729   -1.3292   -0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8229    0.6293    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1570   -1.0500    1.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967    1.2983    0.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3656    0.6306    1.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7233   -0.8533   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1430   -1.6279    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580   -1.2697   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128    0.4707   -1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6890    0.8355    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151    0.6001    1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -1.6042    0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5681   -0.8730   -1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5772    0.4794   -1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460   -1.2153   -1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0307   -2.0368    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1116    2.9655   -0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0593    0.3519    0.6454 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 14 16  1  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  1
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 13 37  1  0
 16 38  1  0
 19 39  1  0
M  END

Synonyms

Value	Source
epsilon-N-(L-Glutar-2-yl)-L-lysine	ChEBI
N-[(S)-5-Amino-5-carboxypentyl]-L-glutamic acid	ChEBI
N6-(L-1,3-Dicarboxypropyl)-L-lysine	ChEBI
L-Saccharopine	Kegg
N-[(S)-5-Amino-5-carboxypentyl]-L-glutamate	Generator
(S)-N-(5-Amino-5-carboxypentyl)-L-glutamic acid	HMDB
L-N-(5-Amino-5-carboxypentyl)-glutamic acid	HMDB
L-Saccharopin	HMDB
N(6)-(L-1,3-Dicarboxypropyl)-L-lysine	HMDB
N-(5-Amino-5-carboxypentyl)-glutamic acid	HMDB
N-(5-Amino-5-carboxypentyl)-L-glutamic acid	HMDB
N-[(5S)-5-Amino-5-carboxypentyl]-L-glutamic acid	HMDB
Saccharopin	HMDB

Molecular Formula

C₁₁H₂₀N₂O₆

Average Mass

276.2863

Monoisotopic Mass

276.132136382

IUPAC Name

(2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid

Traditional Name

saccharopine

CAS Registry Number

Not Available

SMILES

N[C@@H](CCCCN[C@@H](CCC(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1

InChI Key

ZDGJAHTZVHVLOT-YUMQZZPRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Alpha-amino acid
L-alpha-amino acid
Tricarboxylic acid or derivatives
Amino fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

L-lysine derivative (CHEBI:16927 )
amino acid opine (CHEBI:16927 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.25 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-5.4	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.44	ChemAxon
pKa (Strongest Basic)	10.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.95 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	63.95 m³·mol⁻¹	ChemAxon
Polarizability	28.14 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0923000000-1964addb7be546c2a45a	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4j-0913000000-49fae417f545c42253dd	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0923000000-1964addb7be546c2a45a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4j-0913000000-49fae417f545c42253dd	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001u-6950000000-fed481b3c49c1ab6ccd2	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-006x-9220800000-77f63e444994f915feaa	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9240000000-d841eea4ebc5da1106f7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0a4i-0290000000-c0b375ed0505ad2eab6c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0290000000-c0b375ed0505ad2eab6c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-9240000000-d841eea4ebc5da1106f7	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06ur-0190000000-34536967c85ac70477b5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01qi-2790000000-ef0279e3d556894509f0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-6900000000-76748510f1b49f459caf	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0190000000-417ff61b4b14d1bfe5fc	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01u9-1490000000-b4e2c5921f08ff4ee977	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kms-7920000000-32382165ff3ba15b14d6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0059-0190000000-b1accd72c8a2f16e7a71	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9310000000-56c681de611fbd62d1c7	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-f91927cbf4969536ddce	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-dfdb3652043e0e0c5f80	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-1390000000-910bea675f309038db9a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f95-7900000000-1df925bebb97a29a8080	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Blood
Feces
Placenta
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192472	Alpha-aminoadipic semialdehyde synthase, mitochondrial	Unknown	Q9UDR5	Homo sapiens
MMDBp0194066	Probable saccharopine dehydrogenase	Unknown	Q8NBX0	Homo sapiens
MMDBp0194178	Aminoadipate-semialdehyde synthase	Enzyme	A4D0W4	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0002084	Oxoglutaric acid	Water	Aminoadipate-semialdehyde synthase	Saccharopine Dehydrogenase (NADP, L-Lysine Forming), Mitochondrial	VMH; KEGG	30371894
MMDBr0002085	Water	L-Glutamic acid	Aminoadipate-semialdehyde synthase	Saccharopine Dehydrogenase (NAD, L-Glutamate Forming), Mitochondrial	VMH; KEGG	30371894
MMDBr0002583	Water	L-Glutamic acid	Aminoadipate-semialdehyde synthase	N6- (L-1, 3-Dicarboxypropyl)-L-Lysine:NAD+ Oxidoreductase	VMH; KEGG	30371894
MMDBr0006068	Saccharopine	Saccharopine	Not Available	Transport of L-Saccharopinate, Intracellular	VMH	30371894
MMDBr0006069	Saccharopine	Saccharopine	Not Available	Transport of L-Saccharopinate, Extracellular	VMH	30371894
MMDBr0010977	Water	L-Glutamic acid	Not Available	N6-(L-1,3-Dicarboxypropyl)-L-lysine:NAD+ oxidoreductase	VMH	30371894
MMDBr0010992	Water	Oxoglutaric acid	Not Available	N6-(L-1,3-Dicarboxypropyl)-L-lysine:NAD+ oxidoreductase	VMH	30371894
MMDBr0012843	Water	L-Allysine	Saccharopine dehydrogenase [NADP(+), L-glutamate-forming]	Dehydrogenation	RHEA	34755880
MMDBr0013118	Water	alpha-Ketoglutarate	Saccharopine dehydrogenase [NAD(+), L-lysine-forming]	Dehydrogenation	RHEA	34755880
MMDBr0014799	Water	L-Allysine	L-saccharopine oxidase	Oxidation	RHEA	34755880
MMDBr0019595	L-Glutamic acid	Saccharopine	Saccharopine dehydrogenase [NADP(+), L-glutamate-forming]	Dehydrogenation	PathBank	31602464
MMDBr0019596	Saccharopine	L-Lysine	Saccharopine dehydrogenase [NAD(+), L-lysine-forming]	Dehydrogenation	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	11	Human stool; Human feces; Human ; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	2	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	12	Human feces; Human pleural fluid plaque; Human	Metabolic reconstruction
Bacteria	Actinobacteria	4	Human feces; Human	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	10	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified	Children (1-13 years old)	Female	Normal	HMDB	117247
Human Feces	Detected but not Quantified	Not Specified	Both	Normal	HMDB	25486321
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified				HMDB

External Links

HMDB ID

HMDB0000279

DrugBank ID

DB04207

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16927

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Casey RE, Zaleski WA, Philp M, Mendelson IS, MacKenzie SL: Biochemical and clinical studies of a new case of alpha-aminoadipic aciduria. J Inherit Metab Dis. 1978;1(4):129-35. doi: 10.1007/BF01805581. [PubMed:117247 ]
Dancis J, Hutzler J, Cox RP: Familial hyperlysinemia: enzyme studies, diagnostic methods, comments on terminology. Am J Hum Genet. 1979 May;31(3):290-9. [PubMed:463877 ]
Cederbaum SD, Shaw KN, Dancis J, Hutzler J, Blaskovics JC: Hyperlysinemia with saccharopinuria due to combined lysine-ketoglutarate reductase and saccharopine dehydrogenase deficiencies presenting as cystinuria. J Pediatr. 1979 Aug;95(2):234-8. doi: 10.1016/s0022-3476(79)80657-5. [PubMed:571908 ]
Krieger I, Bachmann C, Gronemeyer WH, Cejka J: Propionic acidemia and hyperlysinemia in a case with ornithine transcarbamylase (OTC) deficiency. J Clin Endocrinol Metab. 1976 Oct;43(4):796-802. doi: 10.1210/jcem-43-4-796. [PubMed:977722 ]
Fellows FC, Carson NA: Enzyme studies in a patient with saccharopinuria: a defect of lysine metabolism. Pediatr Res. 1974 Jan;8(1):42-9. doi: 10.1203/00006450-197401000-00008. [PubMed:4809305 ]
Papes F, Kemper EL, Cord-Neto G, Langone F, Arruda P: Lysine degradation through the saccharopine pathway in mammals: involvement of both bifunctional and monofunctional lysine-degrading enzymes in mouse. Biochem J. 1999 Dec 1;344 Pt 2:555-63. [PubMed:10567240 ]
IJlst L, de Kromme I, Oostheim W, Wanders RJ: Molecular cloning and expression of human L-pipecolate oxidase. Biochem Biophys Res Commun. 2000 Apr 21;270(3):1101-5. doi: 10.1006/bbrc.2000.2575. [PubMed:10772957 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Saccharopine (MMDBc0000510)

MOL for #<Metabolite:0x00007fa4a111a268>

3D MOL for #<Metabolite:0x00007fa4a111a268>

3D SDF for #<Metabolite:0x00007fa4a111a268>

3D-SDF for #<Metabolite:0x00007fa4a111a268>

PDB for #<Metabolite:0x00007fa4a111a268>

3D PDB for #<Metabolite:0x00007fa4a111a268>

SMILES for #<Metabolite:0x00007fa4a111a268>

INCHI for #<Metabolite:0x00007fa4a111a268>

Structure for #<Metabolite:0x00007fa4a111a268>

3D Structure for #<Metabolite:0x00007fa4a111a268>