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Showing NP-Card for cysteic acid (NP0250922)

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Record Information
Version2.0
Created at2022-09-07 13:55:53 UTC
Updated at2022-09-07 13:55:53 UTC
NP-MRD IDNP0250922
Secondary Accession NumbersNone
Natural Product Identification
Common Namecysteic acid
DescriptionCysteic acid, also known as cysteate or 3-sulfoalanine, 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). An amino sulfonic acid that is the sulfonic acid analogue of cysteine. Cysteic acid is a very strong basic compound (based on its pKa). Cysteic acid exists in all living species, ranging from bacteria to humans. Within humans, cysteic acid participates in a number of enzymatic reactions. In particular, cysteic acid can be converted into taurine through its interaction with the enzyme cysteine sulfinic acid decarboxylase. In addition, cysteic acid can be converted into taurine through its interaction with the enzyme glutamate decarboxylase 1. cysteic acid is found in Claviceps purpurea, Pinus ponderosa and Puccinia graminis. cysteic acid was first documented in 1988 (PMID: 3240976). In humans, cysteic acid is involved in taurine and hypotaurine metabolism (PMID: 8387962) (PMID: 1547560) (PMID: 21876281) (PMID: 25156684).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0250922 (cysteic acid)


  Mrv0541 02231219352D          

 10  9  0  0  0  0            999 V2000
   22.6051   -9.6576    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.3197  -10.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7472   -9.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1926  -10.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0176   -8.9431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4617   -8.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1762  -10.4826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1762   -9.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8907   -9.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4617   -9.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  2  0  0  0  0
  1  9  1  0  0  0  0
  3 10  1  0  0  0  0
  6 10  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
Download

3D MOL for NP0250922 (cysteic acid)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
    0.4562   -1.4857    0.8116 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6911   -0.4799   -0.1796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2729    0.6782   -0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9449    0.1807   -0.2813 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.3075   -0.8574    0.7705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -0.4148   -1.6474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709    1.5043   -0.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1026   -0.0280   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8849   -0.5564    0.6516 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6025    0.9239   -1.0217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146   -2.3271    0.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3618   -1.8487    1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5134   -0.9433   -1.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1733    1.1725    0.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0382    1.4513   -0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8010    1.2796   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0577    1.7507   -0.7049 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  7  1  0
  4  5  2  0
  4  6  2  0
  2  8  1  0
  8 10  1  0
  8  9  2  0
  1 11  1  0
  1 12  1  0
  2 13  1  6
  3 14  1  0
  3 15  1  0
  7 16  1  0
 10 17  1  0
M  END
Download

3D SDF for NP0250922 (cysteic acid)


  Mrv0541 02231219352D          

 10  9  0  0  0  0            999 V2000
   22.6051   -9.6576    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.3197  -10.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7472   -9.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1926  -10.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0176   -8.9431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4617   -8.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1762  -10.4826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1762   -9.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8907   -9.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4617   -9.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  2  0  0  0  0
  1  9  1  0  0  0  0
  3 10  1  0  0  0  0
  6 10  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250922

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CS(O)(=O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)

> <INCHI_KEY>
XVOYSCVBGLVSOL-UHFFFAOYSA-N

> <FORMULA>
C3H7NO5S

> <MOLECULAR_WEIGHT>
169.156

> <EXACT_MASS>
169.004493029

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
13.559896862018855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.39

> <JCHEM_LOGP>
-2.957299196822919

> <ALOGPS_LOGS>
-0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.2422625178335887

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.7161956659222701

> <JCHEM_PKA_STRONGEST_BASIC>
8.793320902393107

> <JCHEM_POLAR_SURFACE_AREA>
117.68999999999998

> <JCHEM_REFRACTIVITY>
30.435

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cysteic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0250922 (cysteic acid)

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PDB for NP0250922 (cysteic acid)
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  S   UNK     0      42.196 -18.028   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      43.530 -18.798   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      36.861 -18.028   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      41.426 -19.361   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      42.966 -16.694   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      38.195 -15.717   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      39.529 -19.568   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      39.529 -18.028   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      40.863 -17.258   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      38.195 -17.258   0.000  0.00  0.00           C+0
CONECT    1    2    4    5    9                                             
CONECT    2    1                                                            
CONECT    3   10                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6   10                                                            
CONECT    7    8                                                            
CONECT    8    7    9   10                                                  
CONECT    9    1    8                                                       
CONECT   10    3    6    8                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0250922 (cysteic acid)
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SMILES for NP0250922 (cysteic acid)
NC(CS(O)(=O)=O)C(O)=O
Download
INCHI for NP0250922 (cysteic acid)
InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)
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Synonyms
ValueSource
3-SulfoalanineChEBI
beta-SulfoalanineChEBI
Cysteine sulfonic acidChEBI
3-SulphoalanineGenerator
b-SulfoalanineGenerator
b-SulphoalanineGenerator
beta-SulphoalanineGenerator
Β-sulfoalanineGenerator
Β-sulphoalanineGenerator
Cysteine sulfonateGenerator
Cysteine sulphonateGenerator
Cysteine sulphonic acidGenerator
CysteateGenerator
2-Amino-3-sulfopropanoateHMDB
2-Amino-3-sulfopropanoic acidHMDB
2-Amino-3-sulfopropionateHMDB
2-Amino-3-sulfopropionic acidHMDB
CepteateHMDB
Cepteic acidHMDB
CipteateHMDB
Cipteic acidHMDB
CysteinateHMDB
CysteinesulfonateHMDB
Cysteinesulfonic acidHMDB
Cysteinic acidHMDB
CysterateHMDB
Cysteric acidHMDB
L-CysteateHMDB
L-Cysteic acidHMDB
3 SulfoalanineHMDB
Acid, cysteicHMDB
beta SulfoalanineHMDB
Chemical FormulaC3H7NO5S
Average Mass169.1560 Da
Monoisotopic Mass169.00449 Da
IUPAC Name2-amino-3-sulfopropanoic acid
Traditional Namecysteic acid
CAS Registry NumberNot Available
SMILES
NC(CS(O)(=O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)
InChI KeyXVOYSCVBGLVSOL-UHFFFAOYSA-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
Claviceps purpureaLOTUS Database
Pinus ponderosaLOTUS Database
Puccinia graminisLOTUS 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
    • 

  • Organic sulfonic acid or derivatives
    • 

  • Organosulfonic acid or derivatives
    • 

  • Alkanesulfonic acid
    • 

  • Sulfonyl
    • 

  • Organosulfonic acid
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • 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-2.4ALOGPS
logP-3ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)-1.7ChemAxon
pKa (Strongest Basic)8.79ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.44 m³·mol⁻¹ChemAxon
Polarizability13.56 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002757  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023061  
KNApSAcK IDNot Available
Chemspider ID23942  
KEGG Compound IDC00506  
BioCyc IDNot Available
BiGG ID35186  
Wikipedia LinkCysteic_acid  
METLIN ID332  
PubChem Compound25701  
PDB IDNot Available
ChEBI ID21260  
Good Scents IDNot Available
References
General References
  1. Jasin HE: Oxidative modification of inflammatory synovial fluid immunoglobulin G. Inflammation. 1993 Apr;17(2):167-81. [PubMed:8387962  ] 
  2. Sarwar G, Botting HG, Peace RW: Complete amino acid analysis in hydrolysates of foods and feces by liquid chromatography of precolumn phenylisothiocyanate derivatives. J Assoc Off Anal Chem. 1988 Nov-Dec;71(6):1172-5. [PubMed:3240976  ] 
  3. Paroni R, De Vecchi E, Fermo I, Arcelloni C, Diomede L, Magni F, Bonini PA: Total urinary hydroxyproline determined with rapid and simple high-performance liquid chromatography. Clin Chem. 1992 Mar;38(3):407-11. [PubMed:1547560  ] 
  4. Inoue T, Takehara K, Shimizu N, Kitajima Y, Shinohara K, Ito A: Application of XANES profiles to X-ray spectromicroscopy for biomedical specimens: part II. Mapping oxidation state of cysteine in human hair. J Xray Sci Technol. 2011;19(3):313-20. doi: 10.3233/XST-2011-0295. [PubMed:21876281  ] 
  5. Baseggio Conrado A, D'Angelantonio M, Torreggiani A, Pecci L, Fontana M: Reactivity of hypotaurine and cysteine sulfinic acid toward carbonate radical anion and nitrogen dioxide as explored by the peroxidase activity of Cu,Zn superoxide dismutase and by pulse radiolysis. Free Radic Res. 2014 Nov;48(11):1300-10. doi: 10.3109/10715762.2014.951839. Epub  2014 Sep 4. [PubMed:25156684  ] 
  6. LOTUS database [Link]