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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 08:05:53 UTC

Update Date

2021-09-24 08:05:53 UTC

HMDB ID

HMDB0304217

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-hydroxyindole thiazolidine carboxylate

Description

5-hydroxyindole thiazolidine carboxylate belongs to alpha amino acids and derivatives class of compounds. Those are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. 5-hydroxyindole thiazolidine carboxylate is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 5-hydroxyindole thiazolidine carboxylate can be found in a number of food items such as biscuit, common pea, black salsify, and guava, which makes 5-hydroxyindole thiazolidine carboxylate a potential biomarker for the consumption of these food products.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0304217
     RDKit          3D
5-hydroxyindole thiazolidine carboxylate
 33 35  0  0  0  0  0  0  0  0999 V2000
    3.7273   -1.9719    1.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9965   -1.0530    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2400   -1.1137   -0.1405 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0862    0.0539    0.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7192    1.4018    0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920    2.4065    0.6892 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008    1.0048    0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3925    0.9322   -0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5915   -0.1519   -0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4630   -1.3738   -1.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6259   -2.0008   -1.3220 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011   -1.2335   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8137   -1.4003   -0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4893   -0.4163    0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8660    0.7703    0.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5472    1.7529    1.5240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594    0.9270    0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8825   -0.0458   -0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8900   -0.0811    0.9721 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -1.1510   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9202    0.0684   -0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2745    1.7886   -0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572    1.3786    1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614    1.0863    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1352    0.8548   -1.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1368    1.9092   -0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4294   -1.7547   -1.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515   -2.9589   -1.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2873   -2.3424   -0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5302   -0.5944    0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0894    2.4884    1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432    1.8410    0.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -1.0213    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  7 19  1  0
 19  4  1  0
 18  9  1  0
 18 12  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
M  END


  Mrv1533005141521412D          

 19 21  0  0  0  0            999 V2000
   -3.2867    0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9541    0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729   -0.3699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330    0.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615    1.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5410    1.6793    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185    0.3736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 13 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304217

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1CSC(CC2=CNC3=CC=C(O)C=C23)N1

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O3S/c16-8-1-2-10-9(4-8)7(5-14-10)3-12-15-11(6-19-12)13(17)18/h1-2,4-5,11-12,14-16H,3,6H2,(H,17,18)

> <INCHI_KEY>
DFSPELNJAJEWOM-UHFFFAOYSA-N

> <FORMULA>
C13H14N2O3S

> <MOLECULAR_WEIGHT>
278.33

> <EXACT_MASS>
278.072513493

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.89263167250227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(5-hydroxy-1H-indol-3-yl)methyl]-1,3-thiazolidine-4-carboxylic acid

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
-0.8352456348723208

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.67111813181727

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.557382763054723

> <JCHEM_PKA_STRONGEST_BASIC>
8.920588737342168

> <JCHEM_POLAR_SURFACE_AREA>
85.35000000000001

> <JCHEM_REFRACTIVITY>
73.20420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(5-hydroxy-1H-indol-3-yl)methyl]-1,3-thiazolidine-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304217
     RDKit          3D
5-hydroxyindole thiazolidine carboxylate
 33 35  0  0  0  0  0  0  0  0999 V2000
    3.7273   -1.9719    1.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9965   -1.0530    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2400   -1.1137   -0.1405 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0862    0.0539    0.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7192    1.4018    0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920    2.4065    0.6892 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008    1.0048    0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3925    0.9322   -0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5915   -0.1519   -0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4630   -1.3738   -1.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6259   -2.0008   -1.3220 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011   -1.2335   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8137   -1.4003   -0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4893   -0.4163    0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8660    0.7703    0.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5472    1.7529    1.5240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594    0.9270    0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8825   -0.0458   -0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8900   -0.0811    0.9721 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -1.1510   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9202    0.0684   -0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2745    1.7886   -0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572    1.3786    1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614    1.0863    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1352    0.8548   -1.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1368    1.9092   -0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4294   -1.7547   -1.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515   -2.9589   -1.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2873   -2.3424   -0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5302   -0.5944    0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0894    2.4884    1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432    1.8410    0.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -1.0213    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  7 19  1  0
 19  4  1  0
 18  9  1  0
 18 12  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  C   UNK     0      -6.135   0.841   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -7.381   1.746   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -6.296  -0.691   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.728   1.467   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.408   2.974   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0      -2.876   3.135   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -3.395   0.697   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    4                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0304217
HETATM    1  O1  UNL     1       3.727  -1.972   1.310  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.996  -1.053   0.501  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.240  -1.114  -0.140  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.086   0.054   0.206  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.719   1.402   0.574  1.00  0.00           C  
HETATM    6  S1  UNL     1       2.192   2.406   0.689  1.00  0.00           S  
HETATM    7  C4  UNL     1       1.001   1.005   0.688  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.392   0.932  -0.692  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.591  -0.152  -0.836  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.463  -1.374  -1.459  1.00  0.00           C  
HETATM   11  N1  UNL     1      -1.626  -2.001  -1.322  1.00  0.00           N  
HETATM   12  C8  UNL     1      -2.501  -1.233  -0.636  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.814  -1.400  -0.229  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.489  -0.416   0.483  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.866   0.770   0.810  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.547   1.753   1.524  1.00  0.00           O  
HETATM   17  C12 UNL     1      -2.559   0.927   0.400  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.882  -0.046  -0.307  1.00  0.00           C  
HETATM   19  N2  UNL     1       1.890  -0.081   0.972  1.00  0.00           N  
HETATM   20  H1  UNL     1       5.242  -1.151  -1.163  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.920   0.068  -0.891  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.274   1.789  -0.290  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.257   1.379   1.518  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.261   1.086   1.481  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.135   0.855  -1.487  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.137   1.909  -0.852  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.429  -1.755  -1.969  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.852  -2.959  -1.688  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.287  -2.342  -0.496  1.00  0.00           H  
HETATM   30  H11 UNL     1      -5.530  -0.594   0.784  1.00  0.00           H  
HETATM   31  H12 UNL     1      -5.089   2.488   1.043  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.043   1.841   0.637  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.514  -1.021   0.838  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   19   21
CONECT    5    6   22   23
CONECT    6    7
CONECT    7    8   19   24
CONECT    8    9   25   26
CONECT    9   10   10   18
CONECT   10   11   27
CONECT   11   12   28
CONECT   12   13   13   18
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16   17
CONECT   16   31
CONECT   17   18   18   32
CONECT   19   33
END

HMDB0304217
     RDKit          3D
5-hydroxyindole thiazolidine carboxylate
 33 35  0  0  0  0  0  0  0  0999 V2000
    3.7273   -1.9719    1.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9965   -1.0530    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2400   -1.1137   -0.1405 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0862    0.0539    0.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7192    1.4018    0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920    2.4065    0.6892 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008    1.0048    0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3925    0.9322   -0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5915   -0.1519   -0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4630   -1.3738   -1.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6259   -2.0008   -1.3220 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011   -1.2335   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8137   -1.4003   -0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4893   -0.4163    0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8660    0.7703    0.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5472    1.7529    1.5240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594    0.9270    0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8825   -0.0458   -0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8900   -0.0811    0.9721 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -1.1510   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9202    0.0684   -0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2745    1.7886   -0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572    1.3786    1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614    1.0863    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1352    0.8548   -1.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1368    1.9092   -0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4294   -1.7547   -1.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515   -2.9589   -1.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2873   -2.3424   -0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5302   -0.5944    0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0894    2.4884    1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432    1.8410    0.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139   -1.0213    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  7 19  1  0
 19  4  1  0
 18  9  1  0
 18 12  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[(5-Hydroxy-1H-indol-3-yl)methyl]-1,3-thiazolidine-4-carboxylate	Generator
5-Hydroxyindole thiazolidine carboxylic acid	MetaCyc, Generator
2-(3'-(5'-Hydroxyindolyl)methyl)-1,3-thiazolidine-4-carboxylic acid	MeSH

Chemical Formula

C₁₃H₁₄N₂O₃S

Average Molecular Weight

278.33

Monoisotopic Molecular Weight

278.072513493

IUPAC Name

2-[(5-hydroxy-1H-indol-3-yl)methyl]-1,3-thiazolidine-4-carboxylic acid

Traditional Name

2-[(5-hydroxy-1H-indol-3-yl)methyl]-1,3-thiazolidine-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1CSC(CC2=CNC3=CC=C(O)C=C23)N1

InChI Identifier

InChI=1S/C13H14N2O3S/c16-8-1-2-10-9(4-8)7(5-14-10)3-12-15-11(6-19-12)13(17)18/h1-2,4-5,11-12,14-16H,3,6H2,(H,17,18)

InChI Key

DFSPELNJAJEWOM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
3-alkylindole
Hydroxyindole
Indole
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Substituted pyrrole
Benzenoid
Pyrrole
Thiazolidine
Heteroaromatic compound
Amino acid
Azacycle
Organoheterocyclic compound
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Thioether
Hemithioaminal
Dialkylthioether
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Amine
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-11670 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.72	ALOGPS
logP	-0.84	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	1.56	ChemAxon
pKa (Strongest Basic)	8.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	85.35 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.2 m³·mol⁻¹	ChemAxon
Polarizability	27.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	162.68	32859911
AllCCS	[M+H-H2O]+	159.159	32859911
AllCCS	[M+Na]+	166.886	32859911
AllCCS	[M+NH4]+	165.946	32859911
AllCCS	[M-H]-	164.128	32859911
AllCCS	[M+Na-2H]-	163.747	32859911
AllCCS	[M+HCOO]-	163.446	32859911
DeepCCS	[M-2H]-	196.023	30932474
DeepCCS	[M+Na]+	171.484	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-hydroxyindole thiazolidine carboxylate,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)N1	2910.1	Semi standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)N1	2806.0	Standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)N1	3634.9	Standard polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1CSC(CC2=C[NH]C3=CC=C(O[Si](C)(C)C)C=C23)N1[Si](C)(C)C	2908.5	Semi standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1CSC(CC2=C[NH]C3=CC=C(O[Si](C)(C)C)C=C23)N1[Si](C)(C)C	2784.7	Standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1CSC(CC2=C[NH]C3=CC=C(O[Si](C)(C)C)C=C23)N1[Si](C)(C)C	3312.3	Standard polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C)C3=CC=C(O)C=C23)N1[Si](C)(C)C	2881.3	Semi standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C)C3=CC=C(O)C=C23)N1[Si](C)(C)C	2797.8	Standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C)C3=CC=C(O)C=C23)N1[Si](C)(C)C	3376.3	Standard polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C2C(=C1)C(CC1SCC(C(=O)O)N1[Si](C)(C)C)=CN2[Si](C)(C)C	2916.7	Semi standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C2C(=C1)C(CC1SCC(C(=O)O)N1[Si](C)(C)C)=CN2[Si](C)(C)C	2774.3	Standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C2C(=C1)C(CC1SCC(C(=O)O)N1[Si](C)(C)C)=CN2[Si](C)(C)C	3465.8	Standard polar	33892256
5-hydroxyindole thiazolidine carboxylate,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)N1[Si](C)(C)C	2937.6	Semi standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)N1[Si](C)(C)C	2801.6	Standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C23)N1[Si](C)(C)C	3163.4	Standard polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)N1	3550.4	Semi standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)N1	3457.1	Standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)N1	3689.0	Standard polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1CSC(CC2=C[NH]C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)N1[Si](C)(C)C(C)(C)C	3600.1	Semi standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1CSC(CC2=C[NH]C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)N1[Si](C)(C)C(C)(C)C	3450.7	Standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1CSC(CC2=C[NH]C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)N1[Si](C)(C)C(C)(C)C	3519.8	Standard polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C23)N1[Si](C)(C)C(C)(C)C	3542.7	Semi standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C23)N1[Si](C)(C)C(C)(C)C	3432.7	Standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C23)N1[Si](C)(C)C(C)(C)C	3528.4	Standard polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CC1SCC(C(=O)O)N1[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3604.2	Semi standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CC1SCC(C(=O)O)N1[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3409.9	Standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CC1SCC(C(=O)O)N1[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3619.1	Standard polar	33892256
5-hydroxyindole thiazolidine carboxylate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)N1[Si](C)(C)C(C)(C)C	3778.3	Semi standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)N1[Si](C)(C)C(C)(C)C	3564.5	Standard non polar	33892256
5-hydroxyindole thiazolidine carboxylate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CSC(CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C23)N1[Si](C)(C)C(C)(C)C	3439.2	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-hydroxyindole thiazolidine carboxylate 10V, Positive-QTOF	splash10-01t9-0090000000-1acd1db7f968b2562383	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-hydroxyindole thiazolidine carboxylate 20V, Positive-QTOF	splash10-01si-0190000000-d75a5ef112fdc4fa26f7	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-hydroxyindole thiazolidine carboxylate 40V, Positive-QTOF	splash10-0005-1900000000-23f26289e61269101720	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-hydroxyindole thiazolidine carboxylate 10V, Negative-QTOF	splash10-004i-0090000000-3cb7b63ac8f7d6662689	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-hydroxyindole thiazolidine carboxylate 20V, Negative-QTOF	splash10-01si-4390000000-a54e3bd29b9b9c586e32	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-hydroxyindole thiazolidine carboxylate 40V, Negative-QTOF	splash10-001i-9600000000-ccc9ba2e88b0ec24e481	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-hydroxyindole thiazolidine carboxylate 10V, Negative-QTOF	splash10-004i-0190000000-6576924c970f6f4e9590	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-hydroxyindole thiazolidine carboxylate 20V, Negative-QTOF	splash10-0a4i-5940000000-750de626386dda9b6f1f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-hydroxyindole thiazolidine carboxylate 40V, Negative-QTOF	splash10-053r-9600000000-58ae816583ffc9bd6bb2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-hydroxyindole thiazolidine carboxylate 10V, Positive-QTOF	splash10-004i-0090000000-e6eeb2ed1349726f961f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-hydroxyindole thiazolidine carboxylate 20V, Positive-QTOF	splash10-000t-0930000000-68239cab64942eefd788	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-hydroxyindole thiazolidine carboxylate 40V, Positive-QTOF	splash10-0a4i-0960000000-e4b2567b47d1da35cea5	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030575

KNApSAcK ID

Not Available

Chemspider ID

169392

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

195334

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 5-hydroxyindole thiazolidine carboxylate (HMDB0304217)

MOL for HMDB0304217 (5-hydroxyindole thiazolidine carboxylate)

3D MOL for HMDB0304217 (5-hydroxyindole thiazolidine carboxylate)

3D SDF for HMDB0304217 (5-hydroxyindole thiazolidine carboxylate)

3D-SDF for HMDB0304217 (5-hydroxyindole thiazolidine carboxylate)

PDB for HMDB0304217 (5-hydroxyindole thiazolidine carboxylate)

3D PDB for HMDB0304217 (5-hydroxyindole thiazolidine carboxylate)

SMILES for HMDB0304217 (5-hydroxyindole thiazolidine carboxylate)

INCHI for HMDB0304217 (5-hydroxyindole thiazolidine carboxylate)

Structure for HMDB0304217 (5-hydroxyindole thiazolidine carboxylate)

3D Structure for HMDB0304217 (5-hydroxyindole thiazolidine carboxylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra