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Showing NP-Card for L-Cysteinesulfinic acid (NP0002862)

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Record Information
Version1.0
Created at2020-11-23 19:42:16 UTC
Updated at2021-08-12 19:52:21 UTC
NP-MRD IDNP0002862
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Cysteinesulfinic acid
Provided ByBMRBBMRB logo
Description3-Sulfinoalanine, also known as L-cysteinesulfinate, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. In humans, 3-sulfinoalanine is involved in the taurine and hypotaurine metabolism pathway. 3-Sulfinoalanine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. L-Cysteinesulfinic acid is found in Mus musculus and Trypanosoma brucei. It was first documented in 1990 (PMID: 1973601). Based on a literature review a significant number of articles have been published on 3-Sulfinoalanine (PMID: 23455439) (PMID: 17984079) (PMID: 32033212) (PMID: 11071575).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002862 (L-Cysteinesulfinic acid)


     RDKit          2D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.0106   -1.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6065   -0.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7976   -0.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017    0.3539    0.0000 S   0  0  0  0  0  4  0  0  0  0  0  0
    2.4467    1.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3608   -0.5982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342    0.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305    1.9691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6141    0.9476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556   -2.7091    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1697   -0.2771    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0788   -2.1056    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4450    1.2842    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3253   -1.5779    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7649   -0.0705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1418    2.3517    0.0000 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  2  0
  4  6  1  6
  2  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  1
  3 13  1  6
  3 14  1  0
  6 15  1  0
  9 16  1  0
M  END
Download

3D MOL for NP0002862 (L-Cysteinesulfinic acid)

NP0002862
     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.2127   -1.6632   -0.8223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7118   -0.6627    0.1458 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7122   -0.4298   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    0.7394    0.7917 S   0  0  0  0  0  4  0  0  0  0  0  0
    1.0124    2.1535    0.6869 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1915    0.8524    0.2027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6045    0.4995   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5105    0.5685   -0.8948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993    1.6016    0.8531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6057   -2.5122   -0.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9820   -1.2808   -1.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -1.1365    1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925   -1.3890   -0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7202   -0.1447   -1.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8174    0.7561    0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523    2.0479    1.1539 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  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  1
  3 13  1  0
  3 14  1  0
  6 15  1  0
  9 16  1  0
M  END
Download

3D SDF for NP0002862 (L-Cysteinesulfinic acid)


     RDKit          2D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.0106   -1.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6065   -0.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7976   -0.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017    0.3539    0.0000 S   0  0  0  0  0  4  0  0  0  0  0  0
    2.4467    1.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3608   -0.5982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342    0.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305    1.9691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6141    0.9476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556   -2.7091    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1697   -0.2771    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0788   -2.1056    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4450    1.2842    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3253   -1.5779    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7649   -0.0705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1418    2.3517    0.0000 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  2  0
  4  6  1  6
  2  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  1
  3 13  1  6
  3 14  1  0
  6 15  1  0
  9 16  1  0
M  END
> <DATABASE_ID>
NP0002862

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1

> <INCHI_KEY>
ADVPTQAUNPRNPO-REOHCLBHSA-N

> <FORMULA>
C3H7NO4S

> <MOLECULAR_WEIGHT>
153.157

> <EXACT_MASS>
153.009578407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.949980949636586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-[(R)-sulfino]propanoic acid

> <ALOGPS_LOGP>
-2.06

> <JCHEM_LOGP>
-3.82971344535222

> <ALOGPS_LOGS>
-0.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.994188668600013

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1165371093144163

> <JCHEM_PKA_STRONGEST_BASIC>
9.086747204482425

> <JCHEM_POLAR_SURFACE_AREA>
100.62

> <JCHEM_REFRACTIVITY>
28.9921

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.02e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-sulfinoalanine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002862 (L-Cysteinesulfinic acid)

NP0002862
     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.2127   -1.6632   -0.8223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7118   -0.6627    0.1458 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7122   -0.4298   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    0.7394    0.7917 S   0  0  0  0  0  4  0  0  0  0  0  0
    1.0124    2.1535    0.6869 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1915    0.8524    0.2027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6045    0.4995   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5105    0.5685   -0.8948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993    1.6016    0.8531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6057   -2.5122   -0.6774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9820   -1.2808   -1.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -1.1365    1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925   -1.3890   -0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7202   -0.1447   -1.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8174    0.7561    0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523    2.0479    1.1539 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  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  1
  3 13  1  0
  3 14  1  0
  6 15  1  0
  9 16  1  0
M  END
Download

PDB for NP0002862 (L-Cysteinesulfinic acid)

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0    8673.4548673.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8672.1198672.420   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0    8670.7878673.188   0.000  0.00  0.00           S+0
HETATM    4  O   UNK     0    8670.7878674.726   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.4518672.416   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8674.7898672.420   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8676.1198673.188   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8674.7898670.881   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    8673.4548674.726   0.000  0.00  0.00           N+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0002862 (L-Cysteinesulfinic acid)

COMPND    NP0002862
HETATM    1  N1  UNL     1      -1.213  -1.663  -0.822  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.712  -0.663   0.146  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.712  -0.430  -0.225  1.00  0.00           C  
HETATM    4  S1  UNL     1       1.571   0.739   0.792  1.00  0.00           S  
HETATM    5  O1  UNL     1       1.012   2.154   0.687  1.00  0.00           O  
HETATM    6  O2  UNL     1       3.192   0.852   0.203  1.00  0.00           O  
HETATM    7  C3  UNL     1      -1.604   0.499  -0.000  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.510   0.569  -0.895  1.00  0.00           O  
HETATM    9  O4  UNL     1      -1.499   1.602   0.853  1.00  0.00           O  
HETATM   10  H1  UNL     1      -0.606  -2.512  -0.677  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.982  -1.281  -1.772  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.839  -1.136   1.142  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.293  -1.389  -0.207  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.720  -0.145  -1.314  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.817   0.756   0.937  1.00  0.00           H  
HETATM   16  H7  UNL     1      -2.352   2.048   1.154  1.00  0.00           H  
CONECT    1    2   10   11
CONECT    2    3    7   12
CONECT    3    4   13   14
CONECT    4    5    5    6
CONECT    6   15
CONECT    7    8    8    9
CONECT    9   16
END
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SMILES for NP0002862 (L-Cysteinesulfinic acid)

N[C@@H](CS(O)=O)C(O)=O
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INCHI for NP0002862 (L-Cysteinesulfinic acid)

InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1
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View in JSmol
Synonyms
ValueSource
(2R)-2-Amino-3-sulfinopropanoic acidChEBI
3-Sulphino-L-alanineChEBI
L-Cysteinesulfinic acidChEBI
(2R)-2-Amino-3-sulfinopropanoateGenerator
(2R)-2-Amino-3-sulphinopropanoateGenerator
(2R)-2-Amino-3-sulphinopropanoic acidGenerator
3-Sulfino-L-alanineGenerator
L-CysteinesulfinateGenerator
L-CysteinesulphinateGenerator
L-Cysteinesulphinic acidGenerator
3-SulphinoalanineGenerator
3-SulfinoalanineChEBI
3-Sulfinato-L-alaninic acidGenerator, HMDB
3-Sulphinato-L-alaninateGenerator, HMDB
3-Sulphinato-L-alaninic acidGenerator, HMDB
Cysteine hydrogen sulfite esterMeSH, HMDB
Alanine 3-sulfinic acidMeSH, HMDB
Cysteine sulfinateMeSH, HMDB
Cysteine sulfinic acidMeSH, HMDB
3-Sulfinato-L-alaninateHMDB
Alanine-3-sulfinic acidHMDB
Alaninesulfinic acidHMDB
CysteinesulfinateHMDB
Cysteinesulfinic acidHMDB
L-2-Amino-3-sulfinopropionic acidHMDB
Chemical FormulaC3H7NO4S
Average Mass153.1570 Da
Monoisotopic Mass153.00958 Da
IUPAC Name(2R)-2-amino-3-[(R)-sulfino]propanoic acid
Traditional Name3-sulfinoalanine
CAS Registry NumberNot Available
SMILES
N[C@@H](CS(O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1
InChI KeyADVPTQAUNPRNPO-REOHCLBHSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Mus musculusLOTUS Database
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative ParentsNot Available
SubstituentsNot Available
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-2.1ALOGPS
logP-3.8ChemAxon
logS-0.7ALOGPS
pKa (Strongest Acidic)1.12ChemAxon
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.99 m³·mol⁻¹ChemAxon
Polarizability12.95 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000996
DrugBank IDDB02153
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022358
KNApSAcK IDNot Available
Chemspider ID1266065
KEGG Compound IDC00606
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCysteine_sulfinic_acid
METLIN IDNot Available
PubChem Compound1549098
PDB IDCSD
ChEBI ID16345
Good Scents IDNot Available
References
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  2. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  4. Lin SY, Nui DM, Tu CP, Cheng YD, Lin HL: Evidence of L-cysteinesulfinic acid in PKU neonatal hair roots, with disappearance after dietary control. Ultrastruct Pathol. 2000 Sep-Oct;24(5):351-2. doi: 10.1080/019131200750035094. [PubMed:11071575 ]
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