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Showing NP-Card for S-Methylcysteine sulfoxide (NP0045365)

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Record Information
Version2.0
Created at2022-03-17 19:18:41 UTC
Updated at2022-03-17 19:18:41 UTC
NP-MRD IDNP0045365
Secondary Accession NumbersNone
Natural Product Identification
Common NameS-Methylcysteine sulfoxide
Description(S)C(S)S-S-Methylcysteine sulfoxide, also known as kale anemia factor or S-methyl-L-cysteinesulfoxide, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon) (S)C(S)S-S-Methylcysteine sulfoxide is a very strong basic compound (based on its pKa). Outside of the human body, (S)C(S)S-S-Methylcysteine sulfoxide has been detected, but not quantified in, several different foods, such as cabbages, garden onions, soft-necked garlics, and white cabbages. S-Methylcysteine sulfoxide is found in Allium fistulosum, Allium siculum, Brassica napus and Tulbaghia violacea. This could make (S)C(S)S-S-methylcysteine sulfoxide a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045365 (S-Methylcysteine sulfoxide)


  Mrv0541 05061304462D          

  9  8  0  0  0  0            999 V2000
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    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
    2.6664    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  8  2  0  0  0  0
M  END
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3D MOL for NP0045365 (S-Methylcysteine sulfoxide)

     RDKit          3D

 18 17  0  0  0  0  0  0  0  0999 V2000
    2.9618    0.5298    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2279    0.7714   -0.2226 S   0  0  0  0  0  4  0  0  0  0  0  0
    0.7237    1.9157    0.6477 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3672   -0.7285    0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1012   -0.6949   -0.1621 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3470   -0.4277   -1.5786 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596    0.2508    0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7849    0.1889    1.9028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6667    1.2237    0.0974 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6102    1.2936   -0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086    0.4724    1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3408   -0.4595   -0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4916   -0.9779    1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083   -1.5494   -0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4936   -1.7248    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3274   -0.7460   -1.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7331   -1.1177   -2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3266    1.7801    0.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  9  1  0
  7  8  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  1
  6 16  1  0
  6 17  1  0
  9 18  1  0
M  END
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3D SDF for NP0045365 (S-Methylcysteine sulfoxide)


  Mrv0541 05061304462D          

  9  8  0  0  0  0            999 V2000
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    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
    2.6664    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045365

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS(=O)CC(N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO3S/c1-9(8)2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)

> <INCHI_KEY>
ZZLHPCSGGOGHFW-UHFFFAOYSA-N

> <FORMULA>
C4H9NO3S

> <MOLECULAR_WEIGHT>
151.184

> <EXACT_MASS>
151.030313849

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
14.057245356452487

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-methanesulfinylpropanoic acid

> <ALOGPS_LOGP>
-2.56

> <JCHEM_LOGP>
-4.624623685245077

> <ALOGPS_LOGS>
-0.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.609491919121825

> <JCHEM_PKA_STRONGEST_BASIC>
8.448660956659266

> <JCHEM_POLAR_SURFACE_AREA>
80.39000000000001

> <JCHEM_REFRACTIVITY>
34.587700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-methanesulfinylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0045365 (S-Methylcysteine sulfoxide)

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PDB for NP0045365 (S-Methylcysteine sulfoxide)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+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  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.310  -0.206   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.976   3.644   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
HETATM    9  S   UNK     0       4.977   1.334   0.000  0.00  0.00           S+0
CONECT    1    9                                                            
CONECT    2    3    9                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3    6    7                                                  
CONECT    5    3                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    9                                                            
CONECT    9    1    2    8                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0045365 (S-Methylcysteine sulfoxide)
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SMILES for NP0045365 (S-Methylcysteine sulfoxide)
CS(=O)CC(N)C(O)=O
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INCHI for NP0045365 (S-Methylcysteine sulfoxide)
InChI=1S/C4H9NO3S/c1-9(8)2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)
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Synonyms
ValueSource
(S)C(S)S-S-Methylcysteine sulphoxideGenerator
MethyIIn, pyrolyzateHMDB
S-Methylcysteine sulfoxideHMDB
Kale anemia factorHMDB
S-Methyl-L-cysteinesulfoxideHMDB
MethiinHMDB
Methiin, (L-ala)-(S)-isomerHMDB
Methiin, (DL-ala)-isomerHMDB
Methiin, (L-ala)-(R)-isomerHMDB
Methiin, (L-ala)-isomerHMDB
2-Amino-3-methanesulfinylpropanoateGenerator
2-Amino-3-methanesulphinylpropanoateGenerator
2-Amino-3-methanesulphinylpropanoic acidGenerator
S-Methylcysteine sulphoxideGenerator
Chemical FormulaC4H9NO3S
Average Mass151.1840 Da
Monoisotopic Mass151.03031 Da
IUPAC Name2-amino-3-methanesulfinylpropanoic acid
Traditional Name2-amino-3-methanesulfinylpropanoic acid
CAS Registry Number32726-14-0
SMILES
CS(=O)CC(N)C(O)=O
InChI Identifier
InChI=1S/C4H9NO3S/c1-9(8)2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)
InChI KeyZZLHPCSGGOGHFW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium cepaFooDB
Allium fistulosumLOTUS Database
Allium sativumFooDB
Allium siculumLOTUS Database
Brassica napusLOTUS Database
Brassica oleracea var. capitataFooDB
Tulbaghia violaceaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acids  
Alternative Parents
Substituents
  • Alpha-amino acid
    • 

  • Sulfoxide
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Sulfinyl 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 DescriptorsNot Available
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-2.6ALOGPS
logP-4.6ChemAxon
logS-0.48ALOGPS
pKa (Strongest Acidic)1.61ChemAxon
pKa (Strongest Basic)8.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.59 m³·mol⁻¹ChemAxon
Polarizability14.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029432  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000534  
KNApSAcK IDNot Available
Chemspider ID74136  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound82142  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available