Showing NP-Card for L-Cystine (NP0001012)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:38:38 UTC
NP-MRD IDNP0001012
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Cystine
DescriptionCystine is an oxidized dimeric form of cysteine. It is formed by linking two cysteine residues via a disulfide bond (Cys-S-S-Cys) between the -SH groups. Cystine is found in high concentrations in digestive enzymes and in the cells of the immune system, skeletal and connective tissues, skin, and hair. Hair and skin are 10-14% cystine. Cystine is the preferred form of cysteine for the synthesis of glutathione in cells involved in the immune system (e.G. Macrophages and astrocytes). Lymphocytes and neurons prefer cysteine for glutathione production. Optimizing glutathione levels in macrophages and astrocytes with cystine allows these cells to provide cysteine to lymphocytes and neurons directly upon demand (Wikipedia).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001012 (L-Cystine)

  Mrv1652303202019002D          

 14 13  0  0  0  0            999 V2000
    2.5076    0.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931   -0.2350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5076    1.0025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931   -1.0600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3642   -0.2350    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787    0.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2221   -0.2350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937   -0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    0.1775    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4937   -1.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    1.0025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503    0.1775    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0648   -0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2082    0.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  1  1  0  0  0
  2  6  1  0  0  0  0
  5  6  1  0  0  0  0
  7  1  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  1  0  0  0
  9 13  1  0  0  0  0
 12 13  1  0  0  0  0
 14  8  1  0  0  0  0
  5 12  1  0  0  0  0
M  END
Download

3D MOL for NP0001012 (L-Cystine)

HMDB0000192
     RDKit          3D
L-Cystine
 26 25  0  0  0  0  0  0  0  0999 V2000
    2.4477    0.4123   -0.6289 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8759    0.7345    0.7399 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7101    0.3742    1.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2141    1.2915    1.2282 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5507    0.7937   -0.6837 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006   -0.5630   -0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886   -0.3021    0.0629 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7634   -1.5499   -0.0401 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087    0.7844   -0.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040    0.5401   -1.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1965    2.0601   -0.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0130   -0.1468    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309   -0.0330    2.2213 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335   -1.0909    0.2299 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7454   -0.3669   -0.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2621    0.0247   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1495    1.7876    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5168   -0.7059    1.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9790    0.6277    2.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066   -1.4217   -0.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9270   -0.8768   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8536   -0.0969    1.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7983   -1.7967   -1.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1878   -2.3195    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8041    2.8431   -0.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5121   -1.0038   -0.0514 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
  7  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  6
  3 18  1  0
  3 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  1
  8 23  1  0
  8 24  1  0
 11 25  1  0
 14 26  1  0
M  END
Download

3D SDF for NP0001012 (L-Cystine)

  Mrv1652303202019002D          

 14 13  0  0  0  0            999 V2000
    2.5076    0.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931   -0.2350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5076    1.0025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7931   -1.0600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3642   -0.2350    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787    0.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2221   -0.2350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937   -0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    0.1775    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4937   -1.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    1.0025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503    0.1775    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0648   -0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2082    0.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  1  1  0  0  0
  2  6  1  0  0  0  0
  5  6  1  0  0  0  0
  7  1  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  1  0  0  0
  9 13  1  0  0  0  0
 12 13  1  0  0  0  0
 14  8  1  0  0  0  0
  5 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001012

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1

> <INCHI_KEY>
LEVWYRKDKASIDU-IMJSIDKUSA-N

> <FORMULA>
C6H12N2O4S2

> <MOLECULAR_WEIGHT>
240.3

> <EXACT_MASS>
240.023848262

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
22.772305661239265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid

> <ALOGPS_LOGP>
-3.16

> <JCHEM_LOGP>
-5.897687960059564

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.267408279723485

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5564231091903382

> <JCHEM_PKA_STRONGEST_BASIC>
9.342140596747571

> <JCHEM_POLAR_SURFACE_AREA>
126.64000000000001

> <JCHEM_REFRACTIVITY>
54.87179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-cystine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001012 (L-Cystine)

HMDB0000192
     RDKit          3D
L-Cystine
 26 25  0  0  0  0  0  0  0  0999 V2000
    2.4477    0.4123   -0.6289 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8759    0.7345    0.7399 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7101    0.3742    1.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2141    1.2915    1.2282 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5507    0.7937   -0.6837 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006   -0.5630   -0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886   -0.3021    0.0629 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7634   -1.5499   -0.0401 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087    0.7844   -0.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040    0.5401   -1.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1965    2.0601   -0.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0130   -0.1468    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309   -0.0330    2.2213 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335   -1.0909    0.2299 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7454   -0.3669   -0.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2621    0.0247   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1495    1.7876    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5168   -0.7059    1.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9790    0.6277    2.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066   -1.4217   -0.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9270   -0.8768   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8536   -0.0969    1.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7983   -1.7967   -1.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1878   -2.3195    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8041    2.8431   -0.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5121   -1.0038   -0.0514 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
  7  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  6
  3 18  1  0
  3 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  1
  8 23  1  0
  8 24  1  0
 11 25  1  0
 14 26  1  0
M  END
Download

PDB for NP0001012 (L-Cystine)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       4.681   0.331   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.347  -0.439   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.681   1.871   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       3.347  -1.979   0.000  0.00  0.00           N+0
HETATM    5  S   UNK     0       0.680  -0.439   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0       2.014   0.331   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.015  -0.439   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.655  -0.439   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.321   0.331   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.655  -1.979   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -3.321   1.871   0.000  0.00  0.00           N+0
HETATM   12  S   UNK     0      -0.654   0.331   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0      -1.988  -0.439   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.989   0.331   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4    6                                                  
CONECT    3    1                                                            
CONECT    4    2                                                            
CONECT    5    6   12                                                       
CONECT    6    2    5                                                       
CONECT    7    1                                                            
CONECT    8    9   10   14                                                  
CONECT    9    8   11   13                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12   13    5                                                       
CONECT   13    9   12                                                       
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END
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3D PDB for NP0001012 (L-Cystine)

COMPND    HMDB0000192
HETATM    1  N1  UNL     1       2.448   0.412  -0.629  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.876   0.734   0.740  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.710   0.374   1.629  1.00  0.00           C  
HETATM    4  S1  UNL     1       0.214   1.292   1.228  1.00  0.00           S  
HETATM    5  S2  UNL     1      -0.551   0.794  -0.684  1.00  0.00           S  
HETATM    6  C3  UNL     1      -1.701  -0.563  -0.653  1.00  0.00           C  
HETATM    7  C4  UNL     1      -2.989  -0.302   0.063  1.00  0.00           C  
HETATM    8  N2  UNL     1      -3.763  -1.550  -0.040  1.00  0.00           N  
HETATM    9  C5  UNL     1      -3.709   0.784  -0.622  1.00  0.00           C  
HETATM   10  O1  UNL     1      -4.804   0.540  -1.169  1.00  0.00           O  
HETATM   11  O2  UNL     1      -3.196   2.060  -0.669  1.00  0.00           O  
HETATM   12  C6  UNL     1       4.013  -0.147   1.091  1.00  0.00           C  
HETATM   13  O3  UNL     1       4.531  -0.033   2.221  1.00  0.00           O  
HETATM   14  O4  UNL     1       4.533  -1.091   0.230  1.00  0.00           O  
HETATM   15  H1  UNL     1       1.745  -0.367  -0.619  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.262   0.025  -1.173  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.150   1.788   0.785  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.517  -0.706   1.611  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.979   0.628   2.678  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.207  -1.422  -0.108  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.927  -0.877  -1.681  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.854  -0.097   1.144  1.00  0.00           H  
HETATM   23  H9  UNL     1      -3.798  -1.797  -1.067  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.188  -2.319   0.397  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.804   2.843  -0.850  1.00  0.00           H  
HETATM   26  H12 UNL     1       5.512  -1.004  -0.051  1.00  0.00           H  
CONECT    1    2   15   16
CONECT    2    3   12   17
CONECT    3    4   18   19
CONECT    4    5
CONECT    5    6
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23   24
CONECT    9   10   10   11
CONECT   11   25
CONECT   12   13   13   14
CONECT   14   26
END
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SMILES for NP0001012 (L-Cystine)

N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O
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INCHI for NP0001012 (L-Cystine)

InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1
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View in JSmol
Synonyms
Chemical FormulaC6H12N2O4S2
Average Mass240.3000 Da
Monoisotopic Mass240.02385 Da
IUPAC Name(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
Traditional NameL-cystine
CAS Registry Number56-89-3
SMILES
N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1
InChI KeyLEVWYRKDKASIDU-IMJSIDKUSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-cysteine-S-conjugates
Alternative Parents
Substituents
  • L-cysteine-s-conjugate
  • Alpha-amino acid
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Organic disulfide
  • Dialkyldisulfide
  • Amino acid
  • Sulfenyl compound
  • Carboxylic acid
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point260.5 °CNot Available
Boiling Point467.00 to 469.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.19 mg/mLNot Available
LogP-5.08Chmelík, J., Hudecek, J., Putyera, K., Makovicka, J., Kalous, V., & Chmelíková, J. (1991). Characterization of the hydrophobic properties of amino acids on the basis of their partition and distribution coefficients in the 1-octanol-water system. Collection of Czechoslovak chemical communications, 56(10), 2030-2041.
Predicted Properties
PropertyValueSource
Water Solubility16.8 g/LALOGPS
logP-3.2ALOGPS
logP-5.9ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)9.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity54.87 m³·mol⁻¹ChemAxon
Polarizability22.77 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000192
DrugBank IDDB00138
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012672
KNApSAcK IDC00001352
Chemspider ID60997
KEGG Compound IDC00491
BioCyc IDNot Available
BiGG ID35134
Wikipedia LinkCystine
METLIN ID5207
PubChem Compound67678
PDB IDNot Available
ChEBI ID16283
Good Scents IDrw1253521
References
General References