Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:41:42 UTC

HMDB ID

HMDB0000676

Secondary Accession Numbers

HMDB00676

Metabolite Identification

Common Name

L-Homocystine

Description

Homocystine is the oxidized form of homocysteine. Homocystine is a dipeptide consisting of two homocysteine molecules joined by a disulfide bond. Homocysteine is a sulfur-containing amino acid that arises during methionine metabolism. Homocystine occurs only transiently before being reduced to homocysteine and converted to the harmless cystathionine via a vitamin B6-dependent enzyme. Homocystine and homocysteine-cysteine mixed disulfides account for >98% of total homocysteine in plasma from healthy individuals (PMID 11592966 ). Homocystine has been shown to stereospecifically induce endothelial nitric oxide synthase-dependent lipid peroxidation in endothelial cells, thereby inducing a vascular cell type-specific oxidative stress. This vascular stress is associated with atherothrombotic cardiovascular disease (PMID: 14980706 ). High levels of homocysteine (and homocysteine) can be found in individuals suffering from homocystinura due to cystathionine synthase deficiency (PMID: 4685596 )

Structure

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

HMDB0000676
     RDKit          3D
L-Homocystine
 32 31  0  0  0  0  0  0  0  0999 V2000
    3.9753    0.3886    1.0422 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026    0.1944   -0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605   -0.1881   -0.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8187    0.9463   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1662    0.7086   -1.3407 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8766   -0.8727   -0.4149 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074   -0.3644    1.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9362    0.5517    0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9999    0.0392   -0.1604 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9869    1.1129   -0.2790 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6625   -1.1215    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9912   -2.1676    0.6473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9919   -1.0367    0.8304 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524   -0.8042   -0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4279   -1.1277   -1.8205 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8533   -1.4031    0.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8698    0.7329    1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5977   -0.4244    1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4036    1.1897   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262   -1.1141   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9442   -0.3389   -2.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560    1.0554    0.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2426    1.8567   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0899   -1.2441    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0882    0.2087    1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364    0.7696    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5892    1.5512    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5913   -0.1948   -1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4698    2.0074   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4808    1.1980    0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3055   -0.9545    1.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8067   -1.1546    0.6173 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
  9 11  1  0
 11 12  2  0
 11 13  1  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  6
 10 29  1  0
 10 30  1  0
 13 31  1  0
 16 32  1  0
M  END

Homocystine.mol
  Mrv1652305271900182D          

 16 15  0  0  0  0            999 V2000
    2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  6  0  0  0
  1  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
  6  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
 10 12  1  0  0  0  0
  1 13  2  0  0  0  0
  1 14  1  0  0  0  0
 12 15  2  0  0  0  0
 12 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000676

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)/t5-,6?/m0/s1

> <INCHI_KEY>
ZTVZLYBCZNMWCF-ZBHICJROSA-N

> <FORMULA>
C8H16N2O4S2

> <MOLECULAR_WEIGHT>
268.354

> <EXACT_MASS>
268.05514839

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.91822397662728

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid

> <ALOGPS_LOGP>
-4.15

> <JCHEM_LOGP>
-5.3204841436762065

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.403047490886738

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8009555846997536

> <JCHEM_PKA_STRONGEST_BASIC>
9.80244167200791

> <JCHEM_POLAR_SURFACE_AREA>
126.64

> <JCHEM_REFRACTIVITY>
64.38180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000676
     RDKit          3D
L-Homocystine
 32 31  0  0  0  0  0  0  0  0999 V2000
    3.9753    0.3886    1.0422 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026    0.1944   -0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605   -0.1881   -0.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8187    0.9463   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1662    0.7086   -1.3407 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8766   -0.8727   -0.4149 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074   -0.3644    1.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9362    0.5517    0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9999    0.0392   -0.1604 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9869    1.1129   -0.2790 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6625   -1.1215    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9912   -2.1676    0.6473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9919   -1.0367    0.8304 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524   -0.8042   -0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4279   -1.1277   -1.8205 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8533   -1.4031    0.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8698    0.7329    1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5977   -0.4244    1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4036    1.1897   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262   -1.1141   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9442   -0.3389   -2.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560    1.0554    0.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2426    1.8567   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0899   -1.2441    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0882    0.2087    1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364    0.7696    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5892    1.5512    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5913   -0.1948   -1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4698    2.0074   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4808    1.1980    0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3055   -0.9545    1.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8067   -1.1546    0.6173 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
  9 11  1  0
 11 12  2  0
 11 13  1  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  6
 10 29  1  0
 10 30  1  0
 13 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Homocystine.mol                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.080   0.000   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0       0.770  -1.334   0.000  0.00  0.00           S+0
HETATM    7  S   UNK     0      -0.770  -1.334   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -3.080   2.667   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -5.390   1.334   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.160   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.160  -2.667   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -6.160   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -6.160   2.667   0.000  0.00  0.00           O+0
CONECT    1    3   13   14                                                  
CONECT    2    3                                                            
CONECT    3    2    1    4                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   15   16                                                  
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15   12                                                            
CONECT   16   12                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0000676
HETATM    1  N1  UNL     1       3.975   0.389   1.042  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.103   0.194  -0.387  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.761  -0.188  -0.999  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.819   0.946  -0.707  1.00  0.00           C  
HETATM    5  S1  UNL     1       0.166   0.709  -1.341  1.00  0.00           S  
HETATM    6  S2  UNL     1      -0.877  -0.873  -0.415  1.00  0.00           S  
HETATM    7  C4  UNL     1      -1.807  -0.364   1.034  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.936   0.552   0.753  1.00  0.00           C  
HETATM    9  C6  UNL     1      -4.000   0.039  -0.160  1.00  0.00           C  
HETATM   10  N2  UNL     1      -4.987   1.113  -0.279  1.00  0.00           N  
HETATM   11  C7  UNL     1      -4.663  -1.121   0.464  1.00  0.00           C  
HETATM   12  O1  UNL     1      -3.991  -2.168   0.647  1.00  0.00           O  
HETATM   13  O2  UNL     1      -5.992  -1.037   0.830  1.00  0.00           O  
HETATM   14  C8  UNL     1       5.152  -0.804  -0.651  1.00  0.00           C  
HETATM   15  O3  UNL     1       5.428  -1.128  -1.820  1.00  0.00           O  
HETATM   16  O4  UNL     1       5.853  -1.403   0.387  1.00  0.00           O  
HETATM   17  H1  UNL     1       4.870   0.733   1.408  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.598  -0.424   1.547  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.404   1.190  -0.803  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.426  -1.114  -0.478  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.944  -0.339  -2.075  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.756   1.055   0.398  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.243   1.857  -1.177  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.090  -1.244   1.623  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.088   0.209   1.690  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.436   0.770   1.739  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.589   1.551   0.392  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.591  -0.195  -1.166  1.00  0.00           H  
HETATM   29  H13 UNL     1      -4.470   2.007  -0.475  1.00  0.00           H  
HETATM   30  H14 UNL     1      -5.481   1.198   0.642  1.00  0.00           H  
HETATM   31  H15 UNL     1      -6.306  -0.954   1.786  1.00  0.00           H  
HETATM   32  H16 UNL     1       6.807  -1.155   0.617  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3   14   19
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6
CONECT    6    7
CONECT    7    8   24   25
CONECT    8    9   26   27
CONECT    9   10   11   28
CONECT   10   29   30
CONECT   11   12   12   13
CONECT   13   31
CONECT   14   15   15   16
CONECT   16   32
END

HMDB0000676
     RDKit          3D
L-Homocystine
 32 31  0  0  0  0  0  0  0  0999 V2000
    3.9753    0.3886    1.0422 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026    0.1944   -0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605   -0.1881   -0.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8187    0.9463   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1662    0.7086   -1.3407 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8766   -0.8727   -0.4149 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074   -0.3644    1.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9362    0.5517    0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9999    0.0392   -0.1604 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9869    1.1129   -0.2790 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6625   -1.1215    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9912   -2.1676    0.6473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9919   -1.0367    0.8304 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524   -0.8042   -0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4279   -1.1277   -1.8205 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8533   -1.4031    0.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8698    0.7329    1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5977   -0.4244    1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4036    1.1897   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262   -1.1141   -0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9442   -0.3389   -2.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560    1.0554    0.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2426    1.8567   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0899   -1.2441    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0882    0.2087    1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364    0.7696    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5892    1.5512    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5913   -0.1948   -1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4698    2.0074   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4808    1.1980    0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3055   -0.9545    1.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8067   -1.1546    0.6173 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
  9 11  1  0
 11 12  2  0
 11 13  1  0
  2 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  6
 10 29  1  0
 10 30  1  0
 13 31  1  0
 16 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4,4'-Dithiobis(2-aminobutyric acid)	HMDB
4,4'-Dithiobis-2-amino-L-butyrate	HMDB
4,4'-Dithiobis-2-amino-L-butyric acid	HMDB
[S-(R,r)]-4,4'-dithiobis-2-amino-butanoate	HMDB
[S-(R,r)]-4,4'-dithiobis-2-amino-butanoic acid	HMDB
2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoate	HMDB
2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulphanyl}butanoate	HMDB
2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulphanyl}butanoic acid	HMDB

Chemical Formula

C₈H₁₆N₂O₄S₂

Average Molecular Weight

268.354

Monoisotopic Molecular Weight

268.05514839

IUPAC Name

2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid

Traditional Name

2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid

CAS Registry Number

626-72-2

SMILES

NC(CCSSCC[C@H](N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)/t5-,6?/m0/s1

InChI Key

ZTVZLYBCZNMWCF-ZBHICJROSA-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Thia fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Amino acid
Organic disulfide
Dialkyldisulfide
Carboxylic acid
Sulfenyl compound
Organic oxygen compound
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Homocystinuria (HMDB: HMDB0000676)

Disposition

Biological location

Biofluid or Excreta

Cerebrospinal fluid (HMDB: HMDB0000676)

Excreta

Urine (PMID: 2026685)

Non-excretory biofluid

Cerebrospinal Fluid (CSF) (PMID: 14264314)
Blood (PMID: 8745393)

Cellular substructure

Cytoplasm (HMDB: HMDB0000676)
Membrane (HMDB: HMDB0000676)

Source

Endogenous

Endogenous (HMDB: HMDB0000676)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Mallard duck (FooDB: FOOD00353)
Chicken (FooDB: FOOD00329)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Bovine

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Cystathionine beta-Synthase Deficiency (HMDB: HMDB0000676)

Role

Industrial application

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000215)
Homocystinuria (MarkerDB: MDB00000215)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.2 mg/mL at 25 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.5 g/L	ALOGPS
logP	-4.2	ALOGPS
logP	-5.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.8	ChemAxon
pKa (Strongest Basic)	9.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.64 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	64.38 m³·mol⁻¹	ChemAxon
Polarizability	26.92 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	158.663	31661259
DarkChem	[M-H]-	153.578	31661259
AllCCS	[M+H]+	155.248	32859911
AllCCS	[M-H]-	155.501	32859911
DeepCCS	[M+H]+	153.127	30932474
DeepCCS	[M-H]-	149.867	30932474
DeepCCS	[M-2H]-	186.033	30932474
DeepCCS	[M+Na]+	161.836	30932474
AllCCS	[M+H]+	155.2	32859911
AllCCS	[M+H-H2O]+	152.4	32859911
AllCCS	[M+NH4]+	157.9	32859911
AllCCS	[M+Na]+	158.7	32859911
AllCCS	[M-H]-	155.5	32859911
AllCCS	[M+Na-2H]-	156.4	32859911
AllCCS	[M+HCOO]-	157.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Homocystine	NC(CCSSCC[C@H](N)C(O)=O)C(O)=O	3639.5	Standard polar	33892256
L-Homocystine	NC(CCSSCC[C@H](N)C(O)=O)C(O)=O	2181.6	Standard non polar	33892256
L-Homocystine	NC(CCSSCC[C@H](N)C(O)=O)C(O)=O	2723.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Homocystine,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CCSSCCC(N)C(=O)O	2449.8	Semi standard non polar	33892256
L-Homocystine,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CCSSCC[C@H](N)C(=O)O	2476.5	Semi standard non polar	33892256
L-Homocystine,1TMS,isomer #3	C[Si](C)(C)NC(CCSSCC[C@H](N)C(=O)O)C(=O)O	2564.9	Semi standard non polar	33892256
L-Homocystine,1TMS,isomer #4	C[Si](C)(C)N[C@@H](CCSSCCC(N)C(=O)O)C(=O)O	2539.2	Semi standard non polar	33892256
L-Homocystine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CCSSCC[C@H](N)C(=O)O[Si](C)(C)C	2446.7	Semi standard non polar	33892256
L-Homocystine,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CCSSCCC(N)C(=O)O)C(=O)O[Si](C)(C)C	2466.2	Semi standard non polar	33892256
L-Homocystine,2TMS,isomer #3	C[Si](C)(C)NC(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C)C(=O)O	2482.9	Semi standard non polar	33892256
L-Homocystine,2TMS,isomer #4	C[Si](C)(C)NC(CCSSCC[C@H](N)C(=O)O)C(=O)O[Si](C)(C)C	2512.1	Semi standard non polar	33892256
L-Homocystine,2TMS,isomer #5	C[Si](C)(C)N[C@@H](CCSSCCC(N)C(=O)O[Si](C)(C)C)C(=O)O	2494.4	Semi standard non polar	33892256
L-Homocystine,2TMS,isomer #6	C[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C)C(=O)O)C(=O)O	2568.8	Semi standard non polar	33892256
L-Homocystine,2TMS,isomer #7	C[Si](C)(C)N(C(CCSSCC[C@H](N)C(=O)O)C(=O)O)[Si](C)(C)C	2663.8	Semi standard non polar	33892256
L-Homocystine,2TMS,isomer #8	C[Si](C)(C)N([C@@H](CCSSCCC(N)C(=O)O)C(=O)O)[Si](C)(C)C	2639.0	Semi standard non polar	33892256
L-Homocystine,3TMS,isomer #1	C[Si](C)(C)NC(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2500.9	Semi standard non polar	33892256
L-Homocystine,3TMS,isomer #1	C[Si](C)(C)NC(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2554.3	Standard non polar	33892256
L-Homocystine,3TMS,isomer #1	C[Si](C)(C)NC(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	3794.3	Standard polar	33892256
L-Homocystine,3TMS,isomer #10	C[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2681.5	Semi standard non polar	33892256
L-Homocystine,3TMS,isomer #10	C[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2604.7	Standard non polar	33892256
L-Homocystine,3TMS,isomer #10	C[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	3627.2	Standard polar	33892256
L-Homocystine,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CCSSCCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2483.8	Semi standard non polar	33892256
L-Homocystine,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CCSSCCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2546.0	Standard non polar	33892256
L-Homocystine,3TMS,isomer #2	C[Si](C)(C)N[C@@H](CCSSCCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	3813.4	Standard polar	33892256
L-Homocystine,3TMS,isomer #3	C[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O	2528.7	Semi standard non polar	33892256
L-Homocystine,3TMS,isomer #3	C[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O	2559.0	Standard non polar	33892256
L-Homocystine,3TMS,isomer #3	C[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O	3495.6	Standard polar	33892256
L-Homocystine,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CCSSCCC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2607.9	Semi standard non polar	33892256
L-Homocystine,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CCSSCCC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2603.4	Standard non polar	33892256
L-Homocystine,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CCSSCCC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	4078.4	Standard polar	33892256
L-Homocystine,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H](N)CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2617.6	Semi standard non polar	33892256
L-Homocystine,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H](N)CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2626.6	Standard non polar	33892256
L-Homocystine,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H](N)CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	3916.6	Standard polar	33892256
L-Homocystine,3TMS,isomer #6	C[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C	2557.4	Semi standard non polar	33892256
L-Homocystine,3TMS,isomer #6	C[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C	2545.8	Standard non polar	33892256
L-Homocystine,3TMS,isomer #6	C[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C	3487.4	Standard polar	33892256
L-Homocystine,3TMS,isomer #7	C[Si](C)(C)OC(=O)C(CCSSCC[C@H](N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2635.9	Semi standard non polar	33892256
L-Homocystine,3TMS,isomer #7	C[Si](C)(C)OC(=O)C(CCSSCC[C@H](N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2590.4	Standard non polar	33892256
L-Homocystine,3TMS,isomer #7	C[Si](C)(C)OC(=O)C(CCSSCC[C@H](N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	4066.8	Standard polar	33892256
L-Homocystine,3TMS,isomer #8	C[Si](C)(C)OC(=O)C(N)CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2608.6	Semi standard non polar	33892256
L-Homocystine,3TMS,isomer #8	C[Si](C)(C)OC(=O)C(N)CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2615.4	Standard non polar	33892256
L-Homocystine,3TMS,isomer #8	C[Si](C)(C)OC(=O)C(N)CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	3909.1	Standard polar	33892256
L-Homocystine,3TMS,isomer #9	C[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2692.0	Semi standard non polar	33892256
L-Homocystine,3TMS,isomer #9	C[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2604.8	Standard non polar	33892256
L-Homocystine,3TMS,isomer #9	C[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	3643.4	Standard polar	33892256
L-Homocystine,4TMS,isomer #1	C[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2521.9	Semi standard non polar	33892256
L-Homocystine,4TMS,isomer #1	C[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2625.9	Standard non polar	33892256
L-Homocystine,4TMS,isomer #1	C[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	3007.1	Standard polar	33892256
L-Homocystine,4TMS,isomer #2	C[Si](C)(C)OC(=O)C(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2619.2	Semi standard non polar	33892256
L-Homocystine,4TMS,isomer #2	C[Si](C)(C)OC(=O)C(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2681.5	Standard non polar	33892256
L-Homocystine,4TMS,isomer #2	C[Si](C)(C)OC(=O)C(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3623.7	Standard polar	33892256
L-Homocystine,4TMS,isomer #3	C[Si](C)(C)OC(=O)C(N)CCSSCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2606.0	Semi standard non polar	33892256
L-Homocystine,4TMS,isomer #3	C[Si](C)(C)OC(=O)C(N)CCSSCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2679.7	Standard non polar	33892256
L-Homocystine,4TMS,isomer #3	C[Si](C)(C)OC(=O)C(N)CCSSCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3635.4	Standard polar	33892256
L-Homocystine,4TMS,isomer #4	C[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2638.2	Semi standard non polar	33892256
L-Homocystine,4TMS,isomer #4	C[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2693.9	Standard non polar	33892256
L-Homocystine,4TMS,isomer #4	C[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3205.2	Standard polar	33892256
L-Homocystine,4TMS,isomer #5	C[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2639.5	Semi standard non polar	33892256
L-Homocystine,4TMS,isomer #5	C[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2673.0	Standard non polar	33892256
L-Homocystine,4TMS,isomer #5	C[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	3232.5	Standard polar	33892256
L-Homocystine,4TMS,isomer #6	C[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2678.1	Semi standard non polar	33892256
L-Homocystine,4TMS,isomer #6	C[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2668.4	Standard non polar	33892256
L-Homocystine,4TMS,isomer #6	C[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	3243.1	Standard polar	33892256
L-Homocystine,4TMS,isomer #7	C[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2643.2	Semi standard non polar	33892256
L-Homocystine,4TMS,isomer #7	C[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2687.5	Standard non polar	33892256
L-Homocystine,4TMS,isomer #7	C[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3179.1	Standard polar	33892256
L-Homocystine,4TMS,isomer #8	C[Si](C)(C)N(C(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2788.7	Semi standard non polar	33892256
L-Homocystine,4TMS,isomer #8	C[Si](C)(C)N(C(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2754.5	Standard non polar	33892256
L-Homocystine,4TMS,isomer #8	C[Si](C)(C)N(C(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	3353.9	Standard polar	33892256
L-Homocystine,5TMS,isomer #1	C[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2637.6	Semi standard non polar	33892256
L-Homocystine,5TMS,isomer #1	C[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2738.1	Standard non polar	33892256
L-Homocystine,5TMS,isomer #1	C[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2850.5	Standard polar	33892256
L-Homocystine,5TMS,isomer #2	C[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2623.5	Semi standard non polar	33892256
L-Homocystine,5TMS,isomer #2	C[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2734.1	Standard non polar	33892256
L-Homocystine,5TMS,isomer #2	C[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2839.6	Standard polar	33892256
L-Homocystine,5TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2806.8	Semi standard non polar	33892256
L-Homocystine,5TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2803.9	Standard non polar	33892256
L-Homocystine,5TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3017.1	Standard polar	33892256
L-Homocystine,5TMS,isomer #4	C[Si](C)(C)OC(=O)C(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2812.7	Semi standard non polar	33892256
L-Homocystine,5TMS,isomer #4	C[Si](C)(C)OC(=O)C(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2804.7	Standard non polar	33892256
L-Homocystine,5TMS,isomer #4	C[Si](C)(C)OC(=O)C(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3010.8	Standard polar	33892256
L-Homocystine,6TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCSSCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2804.2	Semi standard non polar	33892256
L-Homocystine,6TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCSSCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2831.2	Standard non polar	33892256
L-Homocystine,6TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCSSCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2754.2	Standard polar	33892256
L-Homocystine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCSSCCC(N)C(=O)O	2702.2	Semi standard non polar	33892256
L-Homocystine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCC[C@H](N)C(=O)O	2747.9	Semi standard non polar	33892256
L-Homocystine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N)C(=O)O)C(=O)O	2798.5	Semi standard non polar	33892256
L-Homocystine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(N)C(=O)O)C(=O)O	2780.2	Semi standard non polar	33892256
L-Homocystine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2936.6	Semi standard non polar	33892256
L-Homocystine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2963.7	Semi standard non polar	33892256
L-Homocystine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2961.7	Semi standard non polar	33892256
L-Homocystine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	3013.9	Semi standard non polar	33892256
L-Homocystine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	3005.9	Semi standard non polar	33892256
L-Homocystine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O	3049.8	Semi standard non polar	33892256
L-Homocystine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(CCSSCC[C@H](N)C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	3098.5	Semi standard non polar	33892256
L-Homocystine,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)N([C@@H](CCSSCCC(N)C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	3082.6	Semi standard non polar	33892256
L-Homocystine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3149.5	Semi standard non polar	33892256
L-Homocystine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3152.1	Standard non polar	33892256
L-Homocystine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3769.6	Standard polar	33892256
L-Homocystine,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3368.0	Semi standard non polar	33892256
L-Homocystine,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3152.9	Standard non polar	33892256
L-Homocystine,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3616.1	Standard polar	33892256
L-Homocystine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3150.2	Semi standard non polar	33892256
L-Homocystine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3145.2	Standard non polar	33892256
L-Homocystine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3773.3	Standard polar	33892256
L-Homocystine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	3211.4	Semi standard non polar	33892256
L-Homocystine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	3139.8	Standard non polar	33892256
L-Homocystine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	3526.3	Standard polar	33892256
L-Homocystine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCSSCCC(N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3299.2	Semi standard non polar	33892256
L-Homocystine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCSSCCC(N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3174.2	Standard non polar	33892256
L-Homocystine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCSSCCC(N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3935.9	Standard polar	33892256
L-Homocystine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3284.0	Semi standard non polar	33892256
L-Homocystine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3167.4	Standard non polar	33892256
L-Homocystine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3835.4	Standard polar	33892256
L-Homocystine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	3255.0	Semi standard non polar	33892256
L-Homocystine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	3129.7	Standard non polar	33892256
L-Homocystine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	3518.4	Standard polar	33892256
L-Homocystine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCC[C@H](N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3326.6	Semi standard non polar	33892256
L-Homocystine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCC[C@H](N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3162.6	Standard non polar	33892256
L-Homocystine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCC[C@H](N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3943.9	Standard polar	33892256
L-Homocystine,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3297.7	Semi standard non polar	33892256
L-Homocystine,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3166.2	Standard non polar	33892256
L-Homocystine,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3816.8	Standard polar	33892256
L-Homocystine,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3364.6	Semi standard non polar	33892256
L-Homocystine,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3147.5	Standard non polar	33892256
L-Homocystine,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3631.2	Standard polar	33892256
L-Homocystine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3373.8	Semi standard non polar	33892256
L-Homocystine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3328.2	Standard non polar	33892256
L-Homocystine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3325.3	Standard polar	33892256
L-Homocystine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3476.1	Semi standard non polar	33892256
L-Homocystine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3378.5	Standard non polar	33892256
L-Homocystine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3670.8	Standard polar	33892256
L-Homocystine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3472.6	Semi standard non polar	33892256
L-Homocystine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3368.5	Standard non polar	33892256
L-Homocystine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3663.3	Standard polar	33892256
L-Homocystine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3531.0	Semi standard non polar	33892256
L-Homocystine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3353.0	Standard non polar	33892256
L-Homocystine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3420.8	Standard polar	33892256
L-Homocystine,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3555.8	Semi standard non polar	33892256
L-Homocystine,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3357.1	Standard non polar	33892256
L-Homocystine,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3437.6	Standard polar	33892256
L-Homocystine,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3577.8	Semi standard non polar	33892256
L-Homocystine,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3359.0	Standard non polar	33892256
L-Homocystine,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3443.2	Standard polar	33892256
L-Homocystine,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3565.1	Semi standard non polar	33892256
L-Homocystine,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3357.3	Standard non polar	33892256
L-Homocystine,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3401.9	Standard polar	33892256
L-Homocystine,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)N(C(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3669.1	Semi standard non polar	33892256
L-Homocystine,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)N(C(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3388.9	Standard non polar	33892256
L-Homocystine,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)N(C(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3504.9	Standard polar	33892256
L-Homocystine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3700.7	Semi standard non polar	33892256
L-Homocystine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3532.3	Standard non polar	33892256
L-Homocystine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCSSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3282.7	Standard polar	33892256
L-Homocystine,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3707.0	Semi standard non polar	33892256
L-Homocystine,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3528.6	Standard non polar	33892256
L-Homocystine,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCSSCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3273.0	Standard polar	33892256
L-Homocystine,5TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3861.1	Semi standard non polar	33892256
L-Homocystine,5TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3563.4	Standard non polar	33892256
L-Homocystine,5TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3336.9	Standard polar	33892256
L-Homocystine,5TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3883.2	Semi standard non polar	33892256
L-Homocystine,5TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3572.2	Standard non polar	33892256
L-Homocystine,5TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3330.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - L-Homocystine GC-EI-TOF (Non-derivatized)	splash10-004i-0910000000-965ac587d29ef8ef887e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Homocystine GC-EI-TOF (Non-derivatized)	splash10-004i-1910000000-f9e93d28a230da8e9833	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Homocystine GC-EI-TOF (Non-derivatized)	splash10-004i-0910000000-965ac587d29ef8ef887e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Homocystine GC-EI-TOF (Non-derivatized)	splash10-004i-1910000000-f9e93d28a230da8e9833	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdo-9610000000-e10491cf3224336e3f4a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9322000000-c71d91c4e21c8dc7e38b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Homocystine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homocystine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0900000000-eed9e6a87dcd87f2429a	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homocystine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000i-9200000000-ff66e8130cc84f2f9307	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Homocystine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-000i-9000000000-c290f653e9d9de756e61	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocystine 10V, Positive-QTOF	splash10-0gi0-0290000000-0d5b5e0ed113894b2134	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocystine 20V, Positive-QTOF	splash10-0adi-4940000000-fe801a7a155db92879a5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocystine 40V, Positive-QTOF	splash10-000i-9600000000-fa16bd387fed9ef4ae35	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocystine 10V, Negative-QTOF	splash10-014i-0590000000-079299cfa664ba6bb1b7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocystine 20V, Negative-QTOF	splash10-00lr-2920000000-b1d40f0689b373431812	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocystine 40V, Negative-QTOF	splash10-01bi-9600000000-d4d8be33875dbb26d641	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocystine 10V, Positive-QTOF	splash10-014i-1490000000-14633966e3aac1b76927	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocystine 20V, Positive-QTOF	splash10-001r-3900000000-5e78746bf82c4b74e2da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocystine 40V, Positive-QTOF	splash10-0a4r-9100000000-cf211c8a88522ecadb5f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocystine 10V, Negative-QTOF	splash10-02t9-3920000000-03ece081c0f32738cbb4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocystine 20V, Negative-QTOF	splash10-001i-4900000000-612a915c1fc3a29beb9e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Homocystine 40V, Negative-QTOF	splash10-001i-9100000000-f378c8e7860863830ce2	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<2 uM	Children (1 - 13 years old)	Male	Normal	8745393	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	4.60-12.44 uM	Children (1-13 years old)	Not Specified	Normal	21559159	details
Urine	Detected and Quantified	0-1 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	31506554	details
Urine	Detected and Quantified	0.07 +/- 0.10 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0 - 0.33 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Not Available	details
Urine	Detected and Quantified	4.831 +/- 1.377 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	39 uM	Children (1 - 13 years old)	Male	Homocystinuria	8745393	details
Blood	Detected and Quantified	256.91 uM	Children (1-13 years old)	Female	Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation type	21559159	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0 - 0.2 uM	Children (1-13 years old)	Not Specified	Homocystinuria	14264314	details
Urine	Detected and Quantified	23 umol/mmol creatinine	Children (1 - 13 years old)	Male	Homocystinuria	8745393	details
Urine	Detected and Quantified	230 umol/mmol creatinine	Children (1 - 13 years old)	Female	Homocystinuria due to defect of N(5,10)-methylene THF deficiency	8787431	details
Urine	Detected and Quantified	18.59 +/- 15.858 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation type
Bhardwaj P, Sharma R, Sharma M: Homocystinuria: A rare condition presenting as stroke and megaloblastic anemia. J Pediatr Neurosci. 2010 Jul;5(2):129-31. doi: 10.4103/1817-1745.76110. [PubMed:21559159 ]
Homocystinuria
CARSON NA, DENT CE, FIELD CM, GAULL GE: HOMOCYSTINURIA: CLINICAL AND PATHOLOGICAL REVIEW OF TEN CASES. J Pediatr. 1965 Mar;66:565-83. [PubMed:14264314 ] Kerrin D, Murdoch Eaton D, Livingston J, Henderson M, Smith M: Homocystinuria presenting with sagittal sinus thrombosis in infancy. J Child Neurol. 1996 Jan;11(1):70-1. [PubMed:8745393 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Homocystinuria due to defect of N(5,10)-methylene THF deficiency
Ronge E, Kjellman B: Long term treatment with betaine in methylenetetrahydrofolate reductase deficiency. Arch Dis Child. 1996 Mar;74(3):239-41. [PubMed:8787431 ]

Associated OMIM IDs

250940 (Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation type)
236200 (Homocystinuria)
610247 (Eosinophilic esophagitis)
236250 (Homocystinuria due to defect of N(5,10)-methylene THF deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022176

KNApSAcK ID

Not Available

Chemspider ID

62590

KEGG Compound ID

C01817

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Homocystine

METLIN ID

Not Available

PubChem Compound

69382

PDB ID

Not Available

ChEBI ID

89698

Food Biomarker Ontology

Not Available

VMH ID

LHCYSTIN

MarkerDB ID

MDB00000215

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Haurani FI, Hall CA, Rubin R: Megaloblastic anemia as a result of an abnormal transcobalamin II (Cardeza). J Clin Invest. 1979 Nov;64(5):1253-9. [PubMed:500809 ]
Tomaiuolo M, Vecchione G, Grandone E, Cocomazzi N, Casetta B, Di Minno G, Margaglione M: A new method for determination of plasma homocystine by isotope dilution and electrospray tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Sep 14;842(1):64-9. Epub 2006 Jun 19. [PubMed:16787765 ]
Dudman NP, Guo XW, Crooks R, Xie L, Silberberg JS: Assay of plasma homocysteine: light sensitivity of the fluorescent 7-benzo-2-oxa-1, 3-diazole-4-sulfonic acid derivative, and use of appropriate calibrators. Clin Chem. 1996 Dec;42(12):2028-32. [PubMed:8969644 ]
Kurczynski TW, Muir WA, Fleisher LD, Palomaki JF, Gaull GE, Rassin DK, Abramowsky C: Maternal homocystinuria: studies of an untreated mother and fetus. Arch Dis Child. 1980 Sep;55(9):721-3. [PubMed:7436540 ]
Magera MJ, Lacey JM, Casetta B, Rinaldo P: Method for the determination of total homocysteine in plasma and urine by stable isotope dilution and electrospray tandem mass spectrometry. Clin Chem. 1999 Sep;45(9):1517-22. [PubMed:10471655 ]
Sengupta S, Wehbe C, Majors AK, Ketterer ME, DiBello PM, Jacobsen DW: Relative roles of albumin and ceruloplasmin in the formation of homocystine, homocysteine-cysteine-mixed disulfide, and cystine in circulation. J Biol Chem. 2001 Dec 14;276(50):46896-904. Epub 2001 Oct 9. [PubMed:11592966 ]
Nakano E, Williamson MP, Williams NH, Powers HJ: Copper-mediated LDL oxidation by homocysteine and related compounds depends largely on copper ligation. Biochim Biophys Acta. 2004 Jan 20;1688(1):33-42. [PubMed:14732479 ]
Brown AS, Susser ES: Homocysteine and schizophrenia: from prenatal to adult life. Prog Neuropsychopharmacol Biol Psychiatry. 2005 Sep;29(7):1175-80. [PubMed:16143442 ]
Heydrick SJ, Weiss N, Thomas SR, Cap AP, Pimentel DR, Loscalzo J, Keaney JF Jr: L-Homocysteine and L-homocystine stereospecifically induce endothelial nitric oxide synthase-dependent lipid peroxidation in endothelial cells. Free Radic Biol Med. 2004 Mar 1;36(5):632-40. doi: 10.1016/j.freeradbiomed.2003.12.001. [PubMed:14980706 ]
Wilcken B, Turner B: Homocystinuria. Reduced folate levels during pyridoxine treatment. Arch Dis Child. 1973 Jan;48(1):58-62. doi: 10.1136/adc.48.1.58. [PubMed:4685596 ]

Showing metabocard for L-Homocystine (HMDB0000676)

MOL for HMDB0000676 (L-Homocystine)

3D MOL for HMDB0000676 (L-Homocystine)

3D SDF for HMDB0000676 (L-Homocystine)

3D-SDF for HMDB0000676 (L-Homocystine)

PDB for HMDB0000676 (L-Homocystine)

3D PDB for HMDB0000676 (L-Homocystine)

SMILES for HMDB0000676 (L-Homocystine)

INCHI for HMDB0000676 (L-Homocystine)

Structure for HMDB0000676 (L-Homocystine)

3D Structure for HMDB0000676 (L-Homocystine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra