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Showing NP-Card for s-mercaptocysteine (NP0216294)

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Record Information
Version2.0
Created at2022-09-05 16:11:32 UTC
Updated at2022-09-05 16:11:32 UTC
NP-MRD IDNP0216294
Secondary Accession NumbersNone
Natural Product Identification
Common Names-mercaptocysteine
DescriptionS-Mercaptocysteine, also known as thiocysteine or cysteine persulfide, 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. s-mercaptocysteine is found in Apis cerana. s-mercaptocysteine was first documented in 1997 (PMID: 9099686). S-Mercaptocysteine is a very strong basic compound (based on its pKa) (PMID: 10753862) (PMID: 10760256) (PMID: 12382038) (PMID: 12386155) (PMID: 12686149) (PMID: 14644425).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0216294 (s-mercaptocysteine)


  Mrv0541 02231216262D          

  8  7  0  0  1  0            999 V2000
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    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
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for NP0216294 (s-mercaptocysteine)

     RDKit          3D

 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.5523    1.4767    0.2658 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329    0.3091   -0.5464 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6427   -0.4906   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1027    0.4454   -0.8682 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7904   -0.8186   -0.5700 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7465   -0.5466   -0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0396   -1.6467   -0.6055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4979   -0.1350    1.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2669    2.3303   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0288    1.3728    1.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7894    0.5859   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5142   -1.4147   -0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6817   -0.8116    0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2753   -0.6336    0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5104   -0.0229    0.9586 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
  2  6  1  0
  6  8  1  0
  6  7  2  0
  1  9  1  0
  1 10  1  0
  2 11  1  6
  3 12  1  0
  3 13  1  0
  5 14  1  0
  8 15  1  0
M  END
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3D SDF for NP0216294 (s-mercaptocysteine)


  Mrv0541 02231216262D          

  8  7  0  0  1  0            999 V2000
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    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
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0216294

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H7NO2S2/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1

> <INCHI_KEY>
XBKONSCREBSMCS-REOHCLBHSA-N

> <FORMULA>
C3H7NO2S2

> <MOLECULAR_WEIGHT>
153.223

> <EXACT_MASS>
152.991819853

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.303144702994363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-disulfanylpropanoic acid

> <ALOGPS_LOGP>
-2.04

> <JCHEM_LOGP>
-2.4268166982934516

> <ALOGPS_LOGS>
-1.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.604394519018404

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0417635608407756

> <JCHEM_PKA_STRONGEST_BASIC>
8.901312913994765

> <JCHEM_POLAR_SURFACE_AREA>
63.32

> <JCHEM_REFRACTIVITY>
33.9917

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiocysteine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0216294 (s-mercaptocysteine)

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PDB for NP0216294 (s-mercaptocysteine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       0.976   2.104   0.000  0.00  0.00           S+0
HETATM    5  S   UNK     0      -0.357   1.334   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0216294 (s-mercaptocysteine)
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SMILES for NP0216294 (s-mercaptocysteine)
N[C@@H](CSS)C(O)=O
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INCHI for NP0216294 (s-mercaptocysteine)
InChI=1S/C3H7NO2S2/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
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Synonyms
ValueSource
(R)-2-Amino-3-disulfanylpropanoic acidChEBI
2-Amino-3-disulfanylpropanoic acidChEBI
2-Amino-3-hydrodisulfidopropanoic acidChEBI
2-Amino-3-hydropersulfidopropanoic acidChEBI
2-Amino-3-persulfhydrylpropanoic acidChEBI
3-(Thiosulfeno)-alanineChEBI
Cysteine persulfideChEBI
Cysteine perthiolChEBI
S-SulfanylcysteineChEBI
ThiocysteineChEBI
S-Mercapto-L-cysteineKegg
L-ThiocysteineKegg
(R)-2-Amino-3-disulfanylpropanoateGenerator
(R)-2-Amino-3-disulphanylpropanoateGenerator
(R)-2-Amino-3-disulphanylpropanoic acidGenerator
2-Amino-3-disulfanylpropanoateGenerator
2-Amino-3-disulphanylpropanoateGenerator
2-Amino-3-disulphanylpropanoic acidGenerator
2-Amino-3-hydrodisulfidopropanoateGenerator
2-Amino-3-hydrodisulphidopropanoateGenerator
2-Amino-3-hydrodisulphidopropanoic acidGenerator
2-Amino-3-hydropersulfidopropanoateGenerator
2-Amino-3-hydropersulphidopropanoateGenerator
2-Amino-3-hydropersulphidopropanoic acidGenerator
2-Amino-3-persulfhydrylpropanoateGenerator
2-Amino-3-persulphhydrylpropanoateGenerator
2-Amino-3-persulphhydrylpropanoic acidGenerator
3-(Thiosulpheno)-alanineGenerator
Cysteine persulphideGenerator
S-SulphanylcysteineGenerator
Thiocysteine, (L)-isomerMeSH
Thiocysteine, (D)-isomerMeSH
3-Disulphanyl-L-alanineGenerator
Chemical FormulaC3H7NO2S2
Average Mass153.2230 Da
Monoisotopic Mass152.99182 Da
IUPAC Name(2R)-2-amino-3-disulfanylpropanoic acid
Traditional Namethiocysteine
CAS Registry NumberNot Available
SMILES
N[C@@H](CSS)C(O)=O
InChI Identifier
InChI=1S/C3H7NO2S2/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
InChI KeyXBKONSCREBSMCS-REOHCLBHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS 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
    • 

  • 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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2ALOGPS
logP-2.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)2.04ChemAxon
pKa (Strongest Basic)8.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.99 m³·mol⁻¹ChemAxon
Polarizability14.3 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB02761  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01962  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound165331  
PDB IDNot Available
ChEBI ID28839  
Good Scents IDNot Available
References
General References
  1. Kambampati R, Lauhon CT: Evidence for the transfer of sulfane sulfur from IscS to ThiI during the in vitro biosynthesis of 4-thiouridine in Escherichia coli tRNA. J Biol Chem. 2000 Apr 14;275(15):10727-30. doi: 10.1074/jbc.275.15.10727. [PubMed:10753862  ] 
  2. Clausen T, Kaiser JT, Steegborn C, Huber R, Kessler D: Crystal structure of the cystine C-S lyase from Synechocystis: stabilization of cysteine persulfide for FeS cluster biosynthesis. Proc Natl Acad Sci U S A. 2000 Apr 11;97(8):3856-61. doi: 10.1073/pnas.97.8.3856. [PubMed:10760256  ] 
  3. Mihara H, Esaki N: Bacterial cysteine desulfurases: their function and mechanisms. Appl Microbiol Biotechnol. 2002 Oct;60(1-2):12-23. doi:  10.1007/s00253-002-1107-4. Epub 2002 Sep 4. [PubMed:12382038  ] 
  4. Kaiser JT, Bruno S, Clausen T, Huber R, Schiaretti F, Mozzarelli A, Kessler D: Snapshots of the cystine lyase C-DES during catalysis. Studies in solution and in the crystalline state. J Biol Chem. 2003 Jan 3;278(1):357-65. doi: 10.1074/jbc.M209862200. Epub 2002 Oct  16. [PubMed:12386155  ] 
  5. Kurihara T, Mihara H, Kato S, Yoshimura T, Esaki N: Assembly of iron-sulfur clusters mediated by cysteine desulfurases, IscS, CsdB and CSD, from Escherichia coli. Biochim Biophys Acta. 2003 Apr 11;1647(1-2):303-9. doi:  10.1016/s1570-9639(03)00078-5. [PubMed:12686149  ] 
  6. Ollagnier-de-Choudens S, Lascoux D, Loiseau L, Barras F, Forest E, Fontecave M: Mechanistic studies of the SufS-SufE cysteine desulfurase: evidence for sulfur transfer from SufS to SufE. FEBS Lett. 2003 Dec 4;555(2):263-7. doi: 10.1016/s0014-5793(03)01244-4. [PubMed:14644425  ] 
  7. Wright CM, Christman GD, Snellinger AM, Johnston MV, Mueller EG: Direct evidence for enzyme persulfide and disulfide intermediates during 4-thiouridine biosynthesis. Chem Commun (Camb). 2006 Aug 7;(29):3104-6. doi: 10.1039/b604040c. Epub 2006 Jun  14. [PubMed:16855700  ] 
  8. Leibrecht I, Kessler D: A novel L-cysteine/cystine C-S-lyase directing [2Fe-2S] cluster formation of Synechocystis ferredoxin. J Biol Chem. 1997 Apr 18;272(16):10442-7. doi: 10.1074/jbc.272.16.10442. [PubMed:9099686  ] 
  9. Lang T, Kessler D: Evidence for cysteine persulfide as reaction product of L-Cyst(e)ine C-S-lyase (C-DES) from Synechocystis. Analyses using cystine analogues and recombinant C-DES. J Biol Chem. 1999 Jan 1;274(1):189-95. doi: 10.1074/jbc.274.1.189. [PubMed:9867829  ] 
  10. LOTUS database [Link]