Showing metabocard for Cysteine-S-sulfate (MMDBc0000366)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:36:13 UTC
Update Date2024-10-15 19:09:33 UTC
Metabolite IDMMDBc0000366
Metabolite Identification
Common NameCysteine-S-sulfate
DescriptionCysteine-S-sulfate (SSC) is produced by reaction of inorganic sulfite and cystine by a yet unknown pathway and is a very potent NMDA-receptor agonist. Electrophysiological studies have shown that SSC displays depolarizing properties similar to glutamate. Patients affected with either Molybdenum cofactor deficiency (MOCOD, an autosomal recessive disease that leads to a combined deficiency of the enzymes sulphite oxidase, an enzyme that catalyzes the conversion of sulfite to inorganic sulfate, xanthine dehydrogenase and aldehyde oxidase) or isolated sulphite oxidase deficiency (ISOD, an extremely rare autosomal recessive disorder with identical clinical manifestations to MOCOD) excrete elevated levels of SSC. This rare disorder is associated with brain damage (seizures, spastic quadriplegia, and cerebral atrophy), mental retardation, dislocated ocular lenses, blindness, and excretion in the urine of abnormally large amounts of SSC, sulfite, and thiosulfate but no inorganic sulfate (PMID: 17764028 , 15558695 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f47044582e0>


  Mrv1652305271900072D          

 11 10  0  0  1  0            999 V2000
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f47044582e0>

HMDB0000731
     RDKit          3D
Cysteine-S-sulfate
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.6800    0.6283    1.3057 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6770    0.1058   -0.0582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3413    0.4161   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9850   -0.2722    0.1034 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8405    0.0484   -0.6470 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1010    0.8449   -1.8505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3391   -1.3278   -0.9134 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5985    0.8284    0.6129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8636   -1.3639   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8820   -1.9520   -1.1629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189   -2.1307    1.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732    1.6051    1.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6872    0.6055    1.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810    0.6199   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175    1.5373   -0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439    0.0334   -1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544    1.7015    0.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5528   -1.9280    1.9504 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  2  0
  5  7  2  0
  5  8  1  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  6
  3 15  1  0
  3 16  1  0
  8 17  1  0
 11 18  1  0
M  END
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3D SDF for #<Metabolite:0x00007f47044582e0>


  Mrv1652305271900072D          

 11 10  0  0  1  0            999 V2000
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000366

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H7NO5S2/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1

> <INCHI_KEY>
NOKPBJYHPHHWAN-REOHCLBHSA-N

> <FORMULA>
C3H7NO5S2

> <MOLECULAR_WEIGHT>
201.221

> <EXACT_MASS>
200.976563719

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
16.764815744272703

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-(sulfosulfanyl)propanoic acid

> <ALOGPS_LOGP>
-2.33

> <JCHEM_LOGP>
-2.348351581435501

> <ALOGPS_LOGS>
-0.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.1699046078189745

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.8719924638681862

> <JCHEM_PKA_STRONGEST_BASIC>
8.989135848858341

> <JCHEM_POLAR_SURFACE_AREA>
117.69

> <JCHEM_REFRACTIVITY>
38.642100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.38e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
S-sulphocysteine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f47044582e0>

HMDB0000731
     RDKit          3D
Cysteine-S-sulfate
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.6800    0.6283    1.3057 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6770    0.1058   -0.0582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3413    0.4161   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9850   -0.2722    0.1034 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8405    0.0484   -0.6470 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1010    0.8449   -1.8505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3391   -1.3278   -0.9134 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5985    0.8284    0.6129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8636   -1.3639   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8820   -1.9520   -1.1629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189   -2.1307    1.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732    1.6051    1.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6872    0.6055    1.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810    0.6199   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3175    1.5373   -0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439    0.0334   -1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544    1.7015    0.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5528   -1.9280    1.9504 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  2  0
  5  7  2  0
  5  8  1  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  6
  3 15  1  0
  3 16  1  0
  8 17  1  0
 11 18  1  0
M  END
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PDB for #<Metabolite:0x00007f47044582e0>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0       8.621   4.977   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       5.954   3.437   0.000  0.00  0.00           S+0
HETATM    5  S   UNK     0       4.620   2.667   0.000  0.00  0.00           S+0
HETATM    6  O   UNK     0       3.286   1.897   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.390   1.334   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.850   4.001   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for #<Metabolite:0x00007f47044582e0>

COMPND    HMDB0000731
HETATM    1  N1  UNL     1      -1.680   0.628   1.306  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.677   0.106  -0.058  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.341   0.416  -0.716  1.00  0.00           C  
HETATM    4  S1  UNL     1       0.985  -0.272   0.103  1.00  0.00           S  
HETATM    5  S2  UNL     1       2.840   0.048  -0.647  1.00  0.00           S  
HETATM    6  O1  UNL     1       3.101   0.845  -1.851  1.00  0.00           O  
HETATM    7  O2  UNL     1       3.339  -1.328  -0.913  1.00  0.00           O  
HETATM    8  O3  UNL     1       3.599   0.828   0.613  1.00  0.00           O  
HETATM    9  C3  UNL     1      -1.864  -1.364  -0.056  1.00  0.00           C  
HETATM   10  O4  UNL     1      -1.882  -1.952  -1.163  1.00  0.00           O  
HETATM   11  O5  UNL     1      -2.019  -2.131   1.085  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.073   1.605   1.276  1.00  0.00           H  
HETATM   13  H2  UNL     1      -0.687   0.605   1.632  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.481   0.620  -0.661  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.317   1.537  -0.850  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.444   0.033  -1.774  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.154   1.701   0.723  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.553  -1.928   1.950  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    9   14
CONECT    3    4   15   16
CONECT    4    5
CONECT    5    6    6    7    7
CONECT    5    8
CONECT    8   17
CONECT    9   10   10   11
CONECT   11   18
END
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SMILES for #<Metabolite:0x00007f47044582e0>

N[C@@H](CSS(O)(=O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007f47044582e0>

InChI=1S/C3H7NO5S2/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1
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Synonyms
ValueSource
Cysteine-S-sulfonateChEBI
Cysteinyl-S-sulfonateChEBI
Cysteinyl-S-sulfonic acidChEBI
L-Cysteine hydrogen sulfateChEBI
L-Cysteine S-sulfateChEBI
S-SulfocysteineChEBI
S-SulphO-L-cysteineChEBI
S-SulphocysteineChEBI
Cysteine-S-sulfonic acidGenerator
Cysteine-S-sulphonateGenerator
Cysteine-S-sulphonic acidGenerator
Cysteinyl-S-sulphonateGenerator
Cysteinyl-S-sulphonic acidGenerator
L-Cysteine hydrogen sulfuric acidGenerator
L-Cysteine hydrogen sulphateGenerator
L-Cysteine hydrogen sulphuric acidGenerator
L-Cysteine S-sulfuric acidGenerator
L-Cysteine S-sulphateGenerator
L-Cysteine S-sulphuric acidGenerator
S-SulfO-L-cysteineGenerator
Cysteine-S-sulfuric acidGenerator
Cysteine-S-sulphateGenerator
Cysteine-S-sulphuric acidGenerator
Alaninethiosulfuric acidHMDB
L-Cysteine hydrogen sulfate (ester)HMDB
L-Cysteine hydrogen sulphate (ester)HMDB
L-Cysteine-S-sulfonateHMDB
L-Cysteinesulfonic acidHMDB
S-Cysteinesulfonic acidHMDB
S-Sulphocysteine, monosodium saltHMDB
S-Sulphocysteine ion (1-)HMDB
Molecular FormulaC3H7NO5S2
Average Mass201.221
Monoisotopic Mass200.976563719
IUPAC Name(2R)-2-amino-3-(sulfosulfanyl)propanoic acid
Traditional NameS-sulphocysteine
CAS Registry NumberNot Available
SMILES
N[C@@H](CSS(O)(=O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H7NO5S2/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1
InChI KeyNOKPBJYHPHHWAN-REOHCLBHSA-N