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Showing NP-Card for Cysteine-S-sulfate (NP0000950)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:19:37 UTC
NP-MRD IDNP0000950
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000950 (Cysteine-S-sulfate)


  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 NP0000950 (Cysteine-S-sulfate)

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
Download

3D SDF for NP0000950 (Cysteine-S-sulfate)


  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>
NP0000950

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000950 (Cysteine-S-sulfate)

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
Download

PDB for NP0000950 (Cysteine-S-sulfate)

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 NP0000950 (Cysteine-S-sulfate)

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 NP0000950 (Cysteine-S-sulfate)

N[C@@H](CSS(O)(=O)=O)C(O)=O
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INCHI for NP0000950 (Cysteine-S-sulfate)

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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View in JSmol
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
Chemical FormulaC3H7NO5S2
Average Mass201.2210 Da
Monoisotopic Mass200.97656 Da
IUPAC Name(2R)-2-amino-3-(sulfosulfanyl)propanoic acid
Traditional NameS-sulphocysteine
CAS Registry Number1637-71-4
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-09-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Varshavi.d262021-09-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-09-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Varshavi.d262021-09-05View 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
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-02View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Daphnia pulexLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as s-sulfo-l-cysteines. These are s-conjugated L-cysteine where the S-substituent is specified as a sulfo group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentS-sulfo-L-cysteines
Alternative Parents
Substituents
  • S-sulfo-l-cysteine
  • Alpha-amino acid
  • L-alpha-amino acid
  • S-alkyl thiosulfate
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Sulfenyl compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 - 171 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility53.8 g/LALOGPS
logP-2.3ALOGPS
logP-2.3ChemAxon
logS-0.57ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)8.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.64 m³·mol⁻¹ChemAxon
Polarizability16.76 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000731
DrugBank IDDB04370
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031160
KNApSAcK IDNot Available
Chemspider ID102939
KEGG Compound IDC05824
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound115015
PDB IDNot Available
ChEBI ID27891
Good Scents IDNot Available
References
General References
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  4. Beemer FA, Duran M, Wadman SK, Cats BP: Absence of hepatic molybdenum cofactor. An inborn error of metabolism associated with lens dislocation. Ophthalmic Paediatr Genet. 1985 Apr;5(3):191-5. [PubMed:3877898 ]
  5. Abbas AK, Xia W, Tranberg M, Wigstrom H, Weber SG, Sandberg M: S-sulfo-cysteine is an endogenous amino acid in neonatal rat brain but an unlikely mediator of cysteine neurotoxicity. Neurochem Res. 2008 Feb;33(2):301-7. Epub 2007 Sep 1. [PubMed:17764028 ]
  6. Rashed MS, Saadallah AA, Rahbeeni Z, Eyaid W, Seidahmed MZ, Al-Shahwan S, Salih MA, Osman ME, Al-Amoudi M, Al-Ahaidib L, Jacob M: Determination of urinary S-sulphocysteine, xanthine and hypoxanthine by liquid chromatography-electrospray tandem mass spectrometry. Biomed Chromatogr. 2005 Apr;19(3):223-30. [PubMed:15558695 ]