Showing metabocard for 3-Sulfinoalanine (MMDBc0000381)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:36:31 UTC
Update Date2024-04-30 19:32:02 UTC
Metabolite IDMMDBc0000381
Metabolite Identification
Common Name3-Sulfinoalanine
Description3-Sulfinoalanine or cysteinesulfinic acid is an N-methyl-D-aspartate agonist. It is a product of cysteine dioxygenase or CDO (EC 1.13.11.20). In humans, cysteine catabolism is tightly regulated via regulation of cysteine dioxygenase (CDO) levels in the liver, with the turnover of CDO protein being dramatically decreased when intracellular cysteine levels increase. This occurs in response to changes in the intracellular cysteine concentration via changes in the rate of CDO ubiquitination and degradation. Expressed at high levels in the liver with lower levels in the kidney, brain, and lung, cysteine dioxygenase catalyzes the addition of molecular oxygen to the sulfhydryl group of cysteine, yielding cysteinesulfinic acid. The oxidative catabolism of cysteine to cysteinesulfinate by CDO represents an irreversible loss of cysteine from the free amino acid pool. Once generated, cysteinesulfinate is shuttled into several pathways including hypotaurine/taurine synthesis, sulfite/sulfate production, and the generation of pyruvate.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fa4ac7d58e0>


  Mrv1652303192023122D          

  9  8  0  0  0  0            999 V2000
10003.636210003.4937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.920910003.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.207310003.4937    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10002.207310004.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.491610003.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.351110003.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.063910003.4937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.351110002.2579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.636210004.3177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  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 #<Metabolite:0x00007fa4ac7d58e0>

HMDB0000996
     RDKit          3D
3-Sulfinoalanine
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.0555    1.8671    0.2225 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994    0.5203    0.0073 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8802    0.4453    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106   -1.2234    0.0336 S   0  0  0  0  0  4  0  0  0  0  0  0
    3.0039   -1.2015    0.3684 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577   -1.7275   -1.5712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928   -0.3839    0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067    0.0096    1.6025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -1.7394    0.7952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2516    2.5294    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560    2.1850   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7264    0.2167   -1.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1632    0.8308    1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3839    1.0910   -0.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6141   -1.0442   -2.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6019   -2.3752    0.1749 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  6
  3 13  1  0
  3 14  1  0
  6 15  1  0
  9 16  1  0
M  END
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3D SDF for #<Metabolite:0x00007fa4ac7d58e0>


  Mrv1652303192023122D          

  9  8  0  0  0  0            999 V2000
10003.636210003.4937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.920910003.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.207310003.4937    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10002.207310004.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.491610003.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.351110003.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.063910003.4937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.351110002.2579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.636210004.3177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000381

> <DATABASE_NAME>
MIME

> <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

$$$$
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3D-SDF for #<Metabolite:0x00007fa4ac7d58e0>

HMDB0000996
     RDKit          3D
3-Sulfinoalanine
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.0555    1.8671    0.2225 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994    0.5203    0.0073 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8802    0.4453    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106   -1.2234    0.0336 S   0  0  0  0  0  4  0  0  0  0  0  0
    3.0039   -1.2015    0.3684 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577   -1.7275   -1.5712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928   -0.3839    0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067    0.0096    1.6025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -1.7394    0.7952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2516    2.5294    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560    2.1850   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7264    0.2167   -1.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1632    0.8308    1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3839    1.0910   -0.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6141   -1.0442   -2.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6019   -2.3752    0.1749 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  6
  3 13  1  0
  3 14  1  0
  6 15  1  0
  9 16  1  0
M  END
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PDB for #<Metabolite:0x00007fa4ac7d58e0>

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 #<Metabolite:0x00007fa4ac7d58e0>

COMPND    HMDB0000996
HETATM    1  N1  UNL     1      -1.055   1.867   0.223  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.599   0.520   0.007  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.880   0.445   0.287  1.00  0.00           C  
HETATM    4  S1  UNL     1       1.511  -1.223   0.034  1.00  0.00           S  
HETATM    5  O1  UNL     1       3.004  -1.201   0.368  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.258  -1.728  -1.571  1.00  0.00           O  
HETATM    7  C3  UNL     1      -1.393  -0.384   0.843  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.307   0.010   1.602  1.00  0.00           O  
HETATM    9  O4  UNL     1      -1.123  -1.739   0.795  1.00  0.00           O  
HETATM   10  H1  UNL     1      -0.252   2.529   0.188  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.756   2.185  -0.495  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.726   0.217  -1.070  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.163   0.831   1.275  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.384   1.091  -0.467  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.614  -1.044  -2.195  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.602  -2.375   0.175  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 #<Metabolite:0x00007fa4ac7d58e0>

N[C@@H](CS(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007fa4ac7d58e0>

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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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-Sulfinato-L-alaninic acidHMDB
3-Sulphinato-L-alaninateHMDB
3-Sulphinato-L-alaninic acidHMDB
Cysteine hydrogen sulfite esterHMDB
Alanine 3-sulfinic acidHMDB
Cysteine sulfinateHMDB
Cysteine sulfinic acidHMDB
3-Sulfinato-L-alaninateHMDB
Alanine-3-sulfinic acidHMDB
Alaninesulfinic acidHMDB
CysteinesulfinateHMDB
Cysteinesulfinic acidHMDB
L-2-Amino-3-sulfinopropionic acidHMDB
3-SulfinoalanineChEBI
Molecular FormulaC3H7NO4S
Average Mass153.157
Monoisotopic Mass153.009578407
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