Showing metabocard for Lanthionine (MMDBc0000766)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:54:29 UTC
Update Date2024-04-30 19:33:38 UTC
Metabolite IDMMDBc0000766
Metabolite Identification
Common NameLanthionine
DescriptionLanthionine belongs to the class of organic compounds known as L-cysteine-S-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated. Lanthionine is a uremic toxin (PMID: 30087103 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005645c9de6588>


  Mrv1652306042022272D          

 13 12  0  0  0  0            999 V2000
10000.849210002.0690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.134210002.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.563910002.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.849210001.2436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.419410002.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.134210003.3059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.278710002.0690    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10002.993310002.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.710910002.0690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.424410002.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.710910001.2436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.140010002.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.424410003.3059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  1  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00005645c9de6588>

HMDB0240656
     RDKit          3D
Lanthionine
 25 24  0  0  0  0  0  0  0  0999 V2000
   -2.6726   -1.6431   -0.3195 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6774   -0.3622    0.3538 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2775    0.1885    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207   -0.9081    1.2158 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5301   -0.1813    1.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315   -0.0968   -0.1818 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2166   -1.4479   -0.7011 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5012    0.5008   -0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5045   -0.1766   -0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6932    1.7861    0.4463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650    0.5804   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1773    0.2036   -1.3897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    1.8705    0.1319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8382   -2.1946   -0.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7096   -1.4668   -1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0557   -0.5009    1.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2906    1.1673    0.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9795    0.3290   -0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2124   -0.7610    1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4690    0.8711    1.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4990    0.4818   -0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6923   -2.1007   -0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7377   -1.4654   -1.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4831    2.6183   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6075    2.7080   -0.4168 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
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  1
  3 17  1  0
  3 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  6
  7 22  1  0
  7 23  1  0
 10 24  1  0
 13 25  1  0
M  END
Download

3D SDF for #<Metabolite:0x00005645c9de6588>


  Mrv1652306042022272D          

 13 12  0  0  0  0            999 V2000
10000.849210002.0690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.134210002.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.563910002.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.849210001.2436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.419410002.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.134210003.3059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.278710002.0690    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10002.993310002.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.710910002.0690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.424410002.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.710910001.2436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.140010002.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.424410003.3059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  1  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000766

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12N2O4S/c7-3(5(9)10)1-13-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1

> <INCHI_KEY>
DWPCPZJAHOETAG-IMJSIDKUSA-N

> <FORMULA>
C6H12N2O4S

> <MOLECULAR_WEIGHT>
208.23

> <EXACT_MASS>
208.051778048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.794967332949895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}propanoic acid

> <ALOGPS_LOGP>
-4.06

> <JCHEM_LOGP>
-6.03434669968463

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.4341299418536853

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7056819646375265

> <JCHEM_PKA_STRONGEST_BASIC>
9.441859276427017

> <JCHEM_POLAR_SURFACE_AREA>
126.64000000000001

> <JCHEM_REFRACTIVITY>
46.8575

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lanthionine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00005645c9de6588>

HMDB0240656
     RDKit          3D
Lanthionine
 25 24  0  0  0  0  0  0  0  0999 V2000
   -2.6726   -1.6431   -0.3195 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6774   -0.3622    0.3538 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2775    0.1885    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207   -0.9081    1.2158 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5301   -0.1813    1.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315   -0.0968   -0.1818 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2166   -1.4479   -0.7011 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5012    0.5008   -0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5045   -0.1766   -0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6932    1.7861    0.4463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650    0.5804   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1773    0.2036   -1.3897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    1.8705    0.1319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8382   -2.1946   -0.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7096   -1.4668   -1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0557   -0.5009    1.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2906    1.1673    0.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9795    0.3290   -0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2124   -0.7610    1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4690    0.8711    1.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4990    0.4818   -0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6923   -2.1007   -0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7377   -1.4654   -1.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4831    2.6183   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6075    2.7080   -0.4168 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
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  1
  3 17  1  0
  3 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  6
  7 22  1  0
  7 23  1  0
 10 24  1  0
 13 25  1  0
M  END
Download

PDB for #<Metabolite:0x00005645c9de6588>

HEADER    PROTEIN                                 04-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-20         0                                  
HETATM    1  C   UNK     0    8668.2528670.529   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.9178671.298   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.5868671.298   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8668.2528668.988   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0    8665.5838670.529   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8666.9178672.838   0.000  0.00  0.00           O+0
HETATM    7  S   UNK     0    8670.9208670.529   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0    8672.2548671.298   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.5948670.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8674.9268671.298   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8673.5948668.988   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0    8676.2618670.529   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8674.9268672.838   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   12   13                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for #<Metabolite:0x00005645c9de6588>

COMPND    HMDB0240656
HETATM    1  N1  UNL     1      -2.673  -1.643  -0.320  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.677  -0.362   0.354  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.277   0.188   0.357  1.00  0.00           C  
HETATM    4  S1  UNL     1      -0.121  -0.908   1.216  1.00  0.00           S  
HETATM    5  C3  UNL     1       1.530  -0.181   1.196  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.131  -0.097  -0.182  1.00  0.00           C  
HETATM    7  N2  UNL     1       2.217  -1.448  -0.701  1.00  0.00           N  
HETATM    8  C5  UNL     1       3.501   0.501  -0.033  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.505  -0.177  -0.349  1.00  0.00           O  
HETATM   10  O2  UNL     1       3.693   1.786   0.446  1.00  0.00           O  
HETATM   11  C6  UNL     1      -3.565   0.580  -0.360  1.00  0.00           C  
HETATM   12  O3  UNL     1      -4.177   0.204  -1.390  1.00  0.00           O  
HETATM   13  O4  UNL     1      -3.699   1.871   0.132  1.00  0.00           O  
HETATM   14  H1  UNL     1      -1.838  -2.195  -0.001  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.710  -1.467  -1.328  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.056  -0.501   1.403  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.291   1.167   0.853  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.980   0.329  -0.703  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.212  -0.761   1.865  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.469   0.871   1.579  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.499   0.482  -0.863  1.00  0.00           H  
HETATM   22  H9  UNL     1       2.692  -2.101  -0.011  1.00  0.00           H  
HETATM   23  H10 UNL     1       2.738  -1.465  -1.616  1.00  0.00           H  
HETATM   24  H11 UNL     1       3.483   2.618  -0.127  1.00  0.00           H  
HETATM   25  H12 UNL     1      -3.607   2.708  -0.417  1.00  0.00           H  
CONECT    1    2   14   15
CONECT    2    3   11   16
CONECT    3    4   17   18
CONECT    4    5
CONECT    5    6   19   20
CONECT    6    7    8   21
CONECT    7   22   23
CONECT    8    9    9   10
CONECT   10   24
CONECT   11   12   12   13
CONECT   13   25
END
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SMILES for #<Metabolite:0x00005645c9de6588>

N[C@@H](CSC[C@H](N)C(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00005645c9de6588>

InChI=1S/C6H12N2O4S/c7-3(5(9)10)1-13-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1
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Synonyms
ValueSource
(R)-S-(2-Amino-2-carboxyethyl)-L-cysteineChEBI
(R,R)-2,6-Diamino-4-thiaheptanedioic acidChEBI
(R,R)-3,3'-Thiobis-(2-aminopropanoic acid)ChEBI
(R,R)-Bis(2-amino-2-carboxyethyl)sulfideChEBI
3,3'-Thiobis-L-alanineChEBI
3,3'-Thiodi-L-alanineChEBI
beta,Beta'-thiodi-L-alanineChEBI
(R,R)-2,6-Diamino-4-thiaheptanedioateGenerator
(R,R)-3,3'-Thiobis-(2-aminopropanoate)Generator
(R,R)-Bis(2-amino-2-carboxyethyl)sulphideGenerator
b,Beta'-thiodi-L-alanineGenerator
Β,beta'-thiodi-L-alanineGenerator
3,3'-ThiodialanineHMDB
Lanthionine, (L)-(R)-isomerHMDB
L-LanthionineHMDB
S-[(2R)-2-Amino-2-carboxyethyl]-L-cysteineHMDB
LanthionineMeSH
Molecular FormulaC6H12N2O4S
Average Mass208.23
Monoisotopic Mass208.051778048
IUPAC Name(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}propanoic acid
Traditional Namelanthionine
CAS Registry NumberNot Available
SMILES
N[C@@H](CSC[C@H](N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H12N2O4S/c7-3(5(9)10)1-13-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1
InChI KeyDWPCPZJAHOETAG-IMJSIDKUSA-N