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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:41:40 UTC

HMDB ID

HMDB0000575

Secondary Accession Numbers

HMDB00575

Metabolite Identification

Common Name

DL-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

HMDB0000575
     RDKit          3D
DL-Homocystine
 32 31  0  0  0  0  0  0  0  0999 V2000
    4.4359   -0.1171    1.1369 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188   -0.1779   -0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4197    0.3897   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5701   -0.4083    0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0688    0.4061    0.9476 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8942    0.0896   -0.9869 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352   -1.4355   -0.9428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0274   -1.2171   -0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8860   -0.0932   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1022    1.1137   -0.5941 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0065    0.0871    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8211   -0.8562    0.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1868    1.2707    1.0579 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500    0.5836   -1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1502    0.6363   -2.3475 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7059    1.2633   -0.8224 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2730    0.7650    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4516   -0.2778    1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061   -1.2449   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    1.4329    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069    0.4465   -1.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0093   -0.3228    1.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5053   -1.4621    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2565   -2.3119   -0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2420   -1.6444   -1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899   -0.9176    1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5865   -2.1593    0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2072   -0.3319   -1.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9624    1.4614   -1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4462    1.8572    0.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6122    1.5897    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7990    1.5851    0.1258 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  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 16 32  1  0
M  END

DL-Homocystine.mol
  Mrv1652305271900102D          

 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  0  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
  2  3  1  0  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>
HMDB0000575

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(CCSSCCC(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)

> <INCHI_KEY>
ZTVZLYBCZNMWCF-UHFFFAOYSA-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-[(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>
homocystine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000575
     RDKit          3D
DL-Homocystine
 32 31  0  0  0  0  0  0  0  0999 V2000
    4.4359   -0.1171    1.1369 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188   -0.1779   -0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4197    0.3897   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5701   -0.4083    0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0688    0.4061    0.9476 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8942    0.0896   -0.9869 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352   -1.4355   -0.9428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0274   -1.2171   -0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8860   -0.0932   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1022    1.1137   -0.5941 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0065    0.0871    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8211   -0.8562    0.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1868    1.2707    1.0579 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500    0.5836   -1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1502    0.6363   -2.3475 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7059    1.2633   -0.8224 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2730    0.7650    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4516   -0.2778    1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061   -1.2449   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    1.4329    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069    0.4465   -1.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0093   -0.3228    1.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5053   -1.4621    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2565   -2.3119   -0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2420   -1.6444   -1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899   -0.9176    1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5865   -2.1593    0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2072   -0.3319   -1.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9624    1.4614   -1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4462    1.8572    0.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6122    1.5897    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7990    1.5851    0.1258 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  0
 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: DL-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    HMDB0000575
HETATM    1  N1  UNL     1       4.436  -0.117   1.137  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.819  -0.178  -0.155  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.420   0.390  -0.051  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.570  -0.408   0.947  1.00  0.00           C  
HETATM    5  S1  UNL     1      -0.069   0.406   0.948  1.00  0.00           S  
HETATM    6  S2  UNL     1      -0.894   0.090  -0.987  1.00  0.00           S  
HETATM    7  C4  UNL     1      -1.835  -1.436  -0.943  1.00  0.00           C  
HETATM    8  C5  UNL     1      -3.027  -1.217  -0.013  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.886  -0.093  -0.533  1.00  0.00           C  
HETATM   10  N2  UNL     1      -3.102   1.114  -0.594  1.00  0.00           N  
HETATM   11  C7  UNL     1      -5.007   0.087   0.398  1.00  0.00           C  
HETATM   12  O1  UNL     1      -5.821  -0.856   0.601  1.00  0.00           O  
HETATM   13  O2  UNL     1      -5.187   1.271   1.058  1.00  0.00           O  
HETATM   14  C8  UNL     1       4.550   0.584  -1.165  1.00  0.00           C  
HETATM   15  O3  UNL     1       4.150   0.636  -2.347  1.00  0.00           O  
HETATM   16  O4  UNL     1       5.706   1.263  -0.822  1.00  0.00           O  
HETATM   17  H1  UNL     1       4.273   0.765   1.654  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.452  -0.278   1.047  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.706  -1.245  -0.456  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.529   1.433   0.304  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.907   0.446  -1.034  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.009  -0.323   1.942  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.505  -1.462   0.652  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.257  -2.312  -0.648  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.242  -1.644  -1.958  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.690  -0.918   1.003  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.586  -2.159   0.109  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.207  -0.332  -1.566  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.962   1.461  -1.569  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.446   1.857   0.051  1.00  0.00           H  
HETATM   31  H15 UNL     1      -4.612   1.590   1.831  1.00  0.00           H  
HETATM   32  H16 UNL     1       5.799   1.585   0.126  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

HMDB0000575
     RDKit          3D
DL-Homocystine
 32 31  0  0  0  0  0  0  0  0999 V2000
    4.4359   -0.1171    1.1369 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188   -0.1779   -0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4197    0.3897   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5701   -0.4083    0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0688    0.4061    0.9476 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8942    0.0896   -0.9869 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352   -1.4355   -0.9428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0274   -1.2171   -0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8860   -0.0932   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1022    1.1137   -0.5941 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0065    0.0871    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8211   -0.8562    0.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1868    1.2707    1.0579 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500    0.5836   -1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1502    0.6363   -2.3475 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7059    1.2633   -0.8224 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2730    0.7650    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4516   -0.2778    1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061   -1.2449   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    1.4329    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069    0.4465   -1.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0093   -0.3228    1.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5053   -1.4621    0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2565   -2.3119   -0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2420   -1.6444   -1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899   -0.9176    1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5865   -2.1593    0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2072   -0.3319   -1.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9624    1.4614   -1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4462    1.8572    0.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6122    1.5897    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7990    1.5851    0.1258 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  0
 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)	ChEBI
Homocystine	Kegg
4,4'-Dithiobis(2-aminobutyrate)	Generator
4,4'-Dithiobis	HMDB

Chemical Formula

C₈H₁₆N₂O₄S₂

Average Molecular Weight

268.354

Monoisotopic Molecular Weight

268.05514839

IUPAC Name

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

Traditional Name

homocystine

CAS Registry Number

870-93-9

SMILES

NC(CCSSCCC(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)

InChI Key

ZTVZLYBCZNMWCF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

homocystines (CHEBI:17485 )

Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

MTHFR deficiency (HMDB: HMDB0000575)
Homocystinuria (HMDB: HMDB0000575)
Methylmalonic acidemia (HMDB: HMDB0000575)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9470012)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)

Cellular substructure

Cytoplasm (HMDB: HMDB0000575)

Source

Endogenous

Endogenous (HMDB: HMDB0000575)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
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)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	263 - 265 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	157.888	30932474
[M+H]+	Not Available	158.493	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000020

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]+	159.527	31661259
DarkChem	[M-H]-	153.963	31661259
AllCCS	[M+H]+	155.248	32859911
AllCCS	[M-H]-	155.501	32859911
DeepCCS	[M+H]+	151.448	30932474
DeepCCS	[M-H]-	147.426	30932474
DeepCCS	[M-2H]-	185.307	30932474
DeepCCS	[M+Na]+	160.972	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 Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.27 minutes	32390414
Predicted by Siyang on May 30, 2022	10.5063 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	9.44 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	490.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	483.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	282.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	36.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	62.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	300.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	251.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	965.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	642.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	42.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	665.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	179.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	244.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	772.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	662.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	502.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
DL-Homocystine	NC(CCSSCCC(N)C(O)=O)C(O)=O	3629.9	Standard polar	33892256
DL-Homocystine	NC(CCSSCCC(N)C(O)=O)C(O)=O	2148.6	Standard non polar	33892256
DL-Homocystine	NC(CCSSCCC(N)C(O)=O)C(O)=O	2724.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
DL-Homocystine,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CCSSCCC(N)C(=O)O	2464.0	Semi standard non polar	33892256
DL-Homocystine,1TMS,isomer #2	C[Si](C)(C)NC(CCSSCCC(N)C(=O)O)C(=O)O	2553.4	Semi standard non polar	33892256
DL-Homocystine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(N)CCSSCCC(N)C(=O)O[Si](C)(C)C	2439.8	Semi standard non polar	33892256
DL-Homocystine,2TMS,isomer #2	C[Si](C)(C)NC(CCSSCCC(N)C(=O)O)C(=O)O[Si](C)(C)C	2484.3	Semi standard non polar	33892256
DL-Homocystine,2TMS,isomer #3	C[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C)C(=O)O	2488.2	Semi standard non polar	33892256
DL-Homocystine,2TMS,isomer #4	C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O)C(=O)O	2568.9	Semi standard non polar	33892256
DL-Homocystine,2TMS,isomer #5	C[Si](C)(C)N(C(CCSSCCC(N)C(=O)O)C(=O)O)[Si](C)(C)C	2665.8	Semi standard non polar	33892256
DL-Homocystine,3TMS,isomer #1	C[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2490.8	Semi standard non polar	33892256
DL-Homocystine,3TMS,isomer #1	C[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2544.9	Standard non polar	33892256
DL-Homocystine,3TMS,isomer #1	C[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	3748.7	Standard polar	33892256
DL-Homocystine,3TMS,isomer #2	C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O	2540.9	Semi standard non polar	33892256
DL-Homocystine,3TMS,isomer #2	C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O	2541.0	Standard non polar	33892256
DL-Homocystine,3TMS,isomer #2	C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O	3454.5	Standard polar	33892256
DL-Homocystine,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CCSSCCC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2638.2	Semi standard non polar	33892256
DL-Homocystine,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CCSSCCC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2590.6	Standard non polar	33892256
DL-Homocystine,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CCSSCCC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	4022.5	Standard polar	33892256
DL-Homocystine,3TMS,isomer #4	C[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2630.2	Semi standard non polar	33892256
DL-Homocystine,3TMS,isomer #4	C[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2611.1	Standard non polar	33892256
DL-Homocystine,3TMS,isomer #4	C[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	3873.9	Standard polar	33892256
DL-Homocystine,3TMS,isomer #5	C[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2702.7	Semi standard non polar	33892256
DL-Homocystine,3TMS,isomer #5	C[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2595.0	Standard non polar	33892256
DL-Homocystine,3TMS,isomer #5	C[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	3613.7	Standard polar	33892256
DL-Homocystine,4TMS,isomer #1	C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2522.8	Semi standard non polar	33892256
DL-Homocystine,4TMS,isomer #1	C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2614.1	Standard non polar	33892256
DL-Homocystine,4TMS,isomer #1	C[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2979.9	Standard polar	33892256
DL-Homocystine,4TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2613.3	Semi standard non polar	33892256
DL-Homocystine,4TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2675.1	Standard non polar	33892256
DL-Homocystine,4TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3586.8	Standard polar	33892256
DL-Homocystine,4TMS,isomer #3	C[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2655.4	Semi standard non polar	33892256
DL-Homocystine,4TMS,isomer #3	C[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2682.4	Standard non polar	33892256
DL-Homocystine,4TMS,isomer #3	C[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3182.3	Standard polar	33892256
DL-Homocystine,4TMS,isomer #4	C[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2667.7	Semi standard non polar	33892256
DL-Homocystine,4TMS,isomer #4	C[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2660.3	Standard non polar	33892256
DL-Homocystine,4TMS,isomer #4	C[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	3223.0	Standard polar	33892256
DL-Homocystine,4TMS,isomer #5	C[Si](C)(C)N(C(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2815.9	Semi standard non polar	33892256
DL-Homocystine,4TMS,isomer #5	C[Si](C)(C)N(C(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2749.3	Standard non polar	33892256
DL-Homocystine,4TMS,isomer #5	C[Si](C)(C)N(C(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	3351.5	Standard polar	33892256
DL-Homocystine,5TMS,isomer #1	C[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2626.3	Semi standard non polar	33892256
DL-Homocystine,5TMS,isomer #1	C[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2723.2	Standard non polar	33892256
DL-Homocystine,5TMS,isomer #1	C[Si](C)(C)NC(CCSSCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2838.3	Standard polar	33892256
DL-Homocystine,5TMS,isomer #2	C[Si](C)(C)OC(=O)C(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2820.8	Semi standard non polar	33892256
DL-Homocystine,5TMS,isomer #2	C[Si](C)(C)OC(=O)C(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2794.6	Standard non polar	33892256
DL-Homocystine,5TMS,isomer #2	C[Si](C)(C)OC(=O)C(CCSSCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3027.4	Standard polar	33892256
DL-Homocystine,6TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCSSCCC(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	2802.3	Semi standard non polar	33892256
DL-Homocystine,6TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCSSCCC(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	2823.6	Standard non polar	33892256
DL-Homocystine,6TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCSSCCC(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	2755.3	Standard polar	33892256
DL-Homocystine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(N)C(=O)O	2726.8	Semi standard non polar	33892256
DL-Homocystine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCSSCCC(N)C(=O)O)C(=O)O	2782.6	Semi standard non polar	33892256
DL-Homocystine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C	2943.6	Semi standard non polar	33892256
DL-Homocystine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCSSCCC(N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2991.2	Semi standard non polar	33892256
DL-Homocystine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2991.8	Semi standard non polar	33892256
DL-Homocystine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O	3053.2	Semi standard non polar	33892256
DL-Homocystine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(CCSSCCC(N)C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	3091.9	Semi standard non polar	33892256
DL-Homocystine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3163.1	Semi standard non polar	33892256
DL-Homocystine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3139.0	Standard non polar	33892256
DL-Homocystine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCSSCCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3734.0	Standard polar	33892256
DL-Homocystine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	3235.9	Semi standard non polar	33892256
DL-Homocystine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	3120.0	Standard non polar	33892256
DL-Homocystine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCSSCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	3503.5	Standard polar	33892256
DL-Homocystine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCCC(N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3315.9	Semi standard non polar	33892256
DL-Homocystine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCCC(N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3162.3	Standard non polar	33892256
DL-Homocystine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CCSSCCC(N)C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3907.9	Standard polar	33892256
DL-Homocystine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3293.1	Semi standard non polar	33892256
DL-Homocystine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3155.0	Standard non polar	33892256
DL-Homocystine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3801.6	Standard polar	33892256
DL-Homocystine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3362.6	Semi standard non polar	33892256
DL-Homocystine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3135.9	Standard non polar	33892256
DL-Homocystine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(CCSSCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3619.8	Standard polar	33892256
DL-Homocystine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCSSCCC(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	3374.0	Semi standard non polar	33892256
DL-Homocystine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCSSCCC(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	3317.7	Standard non polar	33892256
DL-Homocystine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCSSCCC(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	3305.7	Standard polar	33892256
DL-Homocystine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)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	3482.0	Semi standard non polar	33892256
DL-Homocystine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)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	3367.0	Standard non polar	33892256
DL-Homocystine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)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	3641.2	Standard polar	33892256
DL-Homocystine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(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	3550.0	Semi standard non polar	33892256
DL-Homocystine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(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	3341.3	Standard non polar	33892256
DL-Homocystine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(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	3403.3	Standard polar	33892256
DL-Homocystine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(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	3568.0	Semi standard non polar	33892256
DL-Homocystine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(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	3347.7	Standard non polar	33892256
DL-Homocystine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(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	3432.0	Standard polar	33892256
DL-Homocystine,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(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	3668.4	Semi standard non polar	33892256
DL-Homocystine,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(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	3369.6	Standard non polar	33892256
DL-Homocystine,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(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	3509.0	Standard polar	33892256
DL-Homocystine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(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
DL-Homocystine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(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	3524.3	Standard non polar	33892256
DL-Homocystine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(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	3267.8	Standard polar	33892256
DL-Homocystine,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(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	3878.9	Semi standard non polar	33892256
DL-Homocystine,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(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	3560.3	Standard non polar	33892256
DL-Homocystine,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(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	3333.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - DL-Homocystine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-004i-0920000000-4772adba6d14b0bf412b	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - DL-Homocystine GC-EI-TOF (Non-derivatized)	splash10-004i-0920000000-4772adba6d14b0bf412b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-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 - DL-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 - DL-Homocystine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - DL-Homocystine GC-MS (TBDMS_2_5) - 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 - DL-Homocystine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0900000000-5c60c8ff83dddb24602e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000i-9200000000-2895a3e74d847e15c6a1	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-000i-9000000000-0a6bc3cbbfaf644160a3	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-014i-0190000000-60f50f1524147fa8c11c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-001i-2920000000-bd3949a66bce9cbb215f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-06e9-9720000000-7031c8ff553e104dc664	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-00di-9210000000-eff737edd37664256745	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-00di-9000000000-560f6dc8247244af6cb4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ , negative-QTOF	splash10-014i-0190000000-dc9f97c5c65a44240b15	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ , negative-QTOF	splash10-001i-2920000000-92fb65949be59e182083	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ , negative-QTOF	splash10-06e9-9720000000-7031c8ff553e104dc664	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ , negative-QTOF	splash10-00di-9210000000-903e4d0b7abc5500ebf1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine LC-ESI-QQ , negative-QTOF	splash10-00di-9000000000-560f6dc8247244af6cb4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine , negative-QTOF	splash10-01x0-6900000000-d82f9d3a2cbf6b1216f0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine 40V, Negative-QTOF	splash10-00di-9000000000-10cb1c86c51258f8a039	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine 20V, Negative-QTOF	splash10-0230-8900000000-e4250a1fffcda8a24732	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine 10V, Negative-QTOF	splash10-0089-3910000000-c79d6d7ce56ddb31e44c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine 35V, Negative-QTOF	splash10-0230-6900000000-a3358bbf41fc201a103c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - DL-Homocystine 35V, Positive-QTOF	splash10-00m0-3920000000-d3fa502c6b1e61f23b21	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DL-Homocystine 10V, Positive-QTOF	splash10-0gi0-0290000000-0d5b5e0ed113894b2134	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DL-Homocystine 20V, Positive-QTOF	splash10-0adi-4940000000-fe801a7a155db92879a5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DL-Homocystine 40V, Positive-QTOF	splash10-000i-9600000000-fa16bd387fed9ef4ae35	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DL-Homocystine 10V, Negative-QTOF	splash10-014i-0590000000-079299cfa664ba6bb1b7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DL-Homocystine 20V, Negative-QTOF	splash10-00lr-2920000000-b1d40f0689b373431812	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - DL-Homocystine 40V, Negative-QTOF	splash10-01bi-9600000000-d4d8be33875dbb26d641	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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

Biospecimen Locations

Blood
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	9.8 +/- 2.8 uM	Adult (>18 years old)	Both	Normal	10588216	details
Blood	Detected and Quantified	0 uM	Adult (>18 years old)	Both	Normal	8456826	details
Urine	Detected and Quantified	0.21 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.0 (0.0-5.0) uM	Adult (>18 years old)	Both	Methylmalonic acidemia and homocystinuria	9470012	details
Blood	Detected and Quantified	122.5 (12.00-233.00) uM	Children (1-13 years old)	Both	Homocystinuria	MetaGene: Metabol...	details
Blood	Detected and Quantified	28-34 uM	Adult (>18 years old)	Male	Methylenetetrahydrofolate reductase deficiency	8456826	details
Urine	Detected and Quantified	22.73 (1-44.47) umol/mmol creatinine	Children (1-13 years old)	Both	Homocystinuria	MetaGene: Metabol...	details

Associated Disorders and Diseases

Disease References

Methylmalonic acidemia
Andersson HC, Shapira E: Biochemical and clinical response to hydroxocobalamin versus cyanocobalamin treatment in patients with methylmalonic acidemia and homocystinuria (cblC). J Pediatr. 1998 Jan;132(1):121-4. [PubMed:9470012 ]
Methylmalonic acidemia and homocystinuria
Andersson HC, Shapira E: Biochemical and clinical response to hydroxocobalamin versus cyanocobalamin treatment in patients with methylmalonic acidemia and homocystinuria (cblC). J Pediatr. 1998 Jan;132(1):121-4. [PubMed:9470012 ]
Homocystinuria
G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Methylenetetrahydrofolate reductase deficiency
Haworth JC, Dilling LA, Surtees RA, Seargeant LE, Lue-Shing H, Cooper BA, Rosenblatt DS: Symptomatic and asymptomatic methylenetetrahydrofolate reductase deficiency in two adult brothers. Am J Med Genet. 1993 Mar 1;45(5):572-6. [PubMed:8456826 ] G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.

Associated OMIM IDs

251000 (Methylmalonic acidemia)
236200 (Homocystinuria)
236250 (Methylenetetrahydrofolate reductase deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022123

KNApSAcK ID

Not Available

Chemspider ID

9616

KEGG Compound ID

C01817

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5557

PubChem Compound

10010

PDB ID

Not Available

ChEBI ID

17485

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Lang, K.; Keller, C. Effect of the cyclophorase system on sulfur-containing amino acids. Biochemische Zeitschrift (1955), 327 202-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Wilcken DE, Gupta VJ: Sulphr containing amino acids in chronic renal failure with particular reference to homocystine and cysteine-homocysteine mixed disulphide. Eur J Clin Invest. 1979 Aug;9(4):301-7. [PubMed:118020 ]
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 DL-Homocystine (HMDB0000575)

MOL for HMDB0000575 (DL-Homocystine)

3D MOL for HMDB0000575 (DL-Homocystine)

3D SDF for HMDB0000575 (DL-Homocystine)

3D-SDF for HMDB0000575 (DL-Homocystine)

PDB for HMDB0000575 (DL-Homocystine)

3D PDB for HMDB0000575 (DL-Homocystine)

SMILES for HMDB0000575 (DL-Homocystine)

INCHI for HMDB0000575 (DL-Homocystine)

Structure for HMDB0000575 (DL-Homocystine)

3D Structure for HMDB0000575 (DL-Homocystine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra