NP-MRD: Showing NP-Card for L-Homocystine (NP0000269)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:14:10 UTC

NP-MRD ID

NP0000269

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Homocystine

Description

Homocystine is the double-bonded form of homocysteine, but it occurs only transiently before being converted to the harmless cystathionine via a vitamin B6-dependent enzyme. Homocystine and homocysteine-cysteine mixed disulfide account for >98% of total homocysteine in plasma from healthy individuals (PMID 11592966 ). Oxidation of low-density lipoprotein (LDL) is thought to be a major factor in the pathophysiology of atherosclerosis. Elevated plasma homocysteine is an accepted risk factor for atherosclerosis, and may act through LDL oxidation, although this is controversial. However, the major thiol in plasma is cysteine, which is present at concentrations approximately 10 times greater than homocysteine; therefore homocystine in plasma is insignificant, and consequently homocystine is unlikely to influence LDL oxidation in vivo (PMID 14732479 ). Increasing evidence supports a role for an elevation of homocysteine in schizophrenia. It has been demonstrated that neural tube defects are related to a genetic defect in homocysteine metabolism. Sufficient intake of folic acid is believed to reduce this risk by enhancing methylation of homocysteine and its conversion to methionine, thereby compensating for this genetic defect (homocystinuria). Plasma homocysteine levels are elevated when folate levels are in the lower half of the normal range (PMID 16143442 ).

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>
NP0000269

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

268.3540 Da

Monoisotopic Mass

268.05515 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	v.dorna83@yahoo.com	Not Available	Not Available	2021-08-10	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Physical Properties

State

Solid

Experimental 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

Predicted 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