MiMeDB: Showing metabocard for Thailandepsin A (MMDBc0016145)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:50:33 UTC

Update Date

2025-10-07 16:06:31 UTC

Metabolite ID

MMDBc0016145

Metabolite Identification

Common Name

Thailandepsin A

Description

Thailandepsin A is a novel class I histone deacetylase (HDAC) inhibitor derived from the bacterium Burkholderia thailandensis. Its chemical structure features a unique depsipeptide backbone, which is critical for its biological activity. Thailandepsin A exhibits broad anti-proliferative effects across various cancer types, including neuroendocrine and anaplastic thyroid cancers, by modulating key cellular pathways such as the Notch signaling pathway, which is implicated in cell differentiation and proliferation (PMID:29050323 ). Additionally, it has been shown to enhance SSTR2 expression in pulmonary carcinoid cell lines, indicating its potential role in neuroendocrine tumor therapy (PMID:31163616 ). The compound is also being explored in innovative drug delivery systems, such as thailandepsin A-loaded micelles for targeted cancer therapy, highlighting its versatility in therapeutic applications (PMID:26994874 ). Furthermore, studies have demonstrated its efficacy in inducing apoptosis and DNA damage response in ovarian cancer cells (PMID:22531354 ). Overall, thailandepsin A represents a promising candidate in the field of cancer therapeutics, with its potent HDAC inhibitory activities and potential for further development (PMID:22246221 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152108502D          

 41 42  0  0  1  0            999 V2000
    5.7072   -2.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7517   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8114    3.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041   -1.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1998   -0.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -1.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0055   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765    2.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -1.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550    2.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4072   -0.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0499   -1.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0316    0.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0263   -1.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0086   -0.1134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5214    2.0012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5668    1.1781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8613   -1.2807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5953    0.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -1.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232   -0.5740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3686    1.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900    0.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9800    1.3259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2056    1.9305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7532    0.1730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3695   -1.9306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865    0.7945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8267   -2.2766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    2.7980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219    1.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5172   -0.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    3.5761    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0966   -0.8936    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6185   -0.2174    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7294   -1.4372    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6893    0.3526    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9776    2.6886    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0949    1.8119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3532   -0.6308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -0.1423    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  6  1  4  0  0  0
  7  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  4  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 14  1  1  0  0  0
 21 18  1  0  0  0  0
 22 16  1  0  0  0  0
 23 17  1  0  0  0  0
 24 16  1  0  0  0  0
 24 19  2  0  0  0  0
 25 17  1  0  0  0  0
 25 22  2  0  0  0  0
 26 21  1  0  0  0  0
 26 23  2  0  0  0  0
 18 27  1  6  0  0  0
 19 28  1  4  0  0  0
 29 20  2  0  0  0  0
 22 30  1  4  0  0  0
 23 31  1  4  0  0  0
 32 15  1  0  0  0  0
 32 20  1  0  0  0  0
 33  3  1  0  0  0  0
 33 10  1  0  0  0  0
 34  9  1  0  0  0  0
 35 13  1  0  0  0  0
 35 34  1  0  0  0  0
 36 14  1  0  0  0  0
 15 37  1  6  0  0  0
 16 38  1  1  0  0  0
 17 39  1  6  0  0  0
 18 40  1  6  0  0  0
 21 41  1  1  0  0  0
M  END


  Mrv1652305152108502D          

 41 42  0  0  1  0            999 V2000
    5.7072   -2.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7517   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8114    3.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041   -1.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1998   -0.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365   -1.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0055   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765    2.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242   -1.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550    2.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4072   -0.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0499   -1.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0316    0.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0263   -1.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0086   -0.1134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5214    2.0012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5668    1.1781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8613   -1.2807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5953    0.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -1.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232   -0.5740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3686    1.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900    0.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9800    1.3259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2056    1.9305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7532    0.1730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3695   -1.9306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865    0.7945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8267   -2.2766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    2.7980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219    1.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5172   -0.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    3.5761    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0966   -0.8936    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6185   -0.2174    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7294   -1.4372    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6893    0.3526    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9776    2.6886    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0949    1.8119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3532   -0.6308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -0.1423    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  6  1  4  0  0  0
  7  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  4  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 14  1  1  0  0  0
 21 18  1  0  0  0  0
 22 16  1  0  0  0  0
 23 17  1  0  0  0  0
 24 16  1  0  0  0  0
 24 19  2  0  0  0  0
 25 17  1  0  0  0  0
 25 22  2  0  0  0  0
 26 21  1  0  0  0  0
 26 23  2  0  0  0  0
 18 27  1  6  0  0  0
 19 28  1  4  0  0  0
 29 20  2  0  0  0  0
 22 30  1  4  0  0  0
 23 31  1  4  0  0  0
 32 15  1  0  0  0  0
 32 20  1  0  0  0  0
 33  3  1  0  0  0  0
 33 10  1  0  0  0  0
 34  9  1  0  0  0  0
 35 13  1  0  0  0  0
 35 34  1  0  0  0  0
 36 14  1  0  0  0  0
 15 37  1  6  0  0  0
 16 38  1  1  0  0  0
 17 39  1  6  0  0  0
 18 40  1  6  0  0  0
 21 41  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0016145

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(C)(CC)[C@@]1([H])N=C(O)[C@@]2([H])CSSCCC=C[C@]([H])(CC(O)=N[C@]([H])(CCSC)C(O)=N2)OC(=O)C[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C23H37N3O6S3/c1-4-14(2)21-18(27)12-20(29)32-15-7-5-6-9-34-35-13-17(23(31)26-21)25-22(30)16(8-10-33-3)24-19(28)11-15/h5,7,14-18,21,27H,4,6,8-13H2,1-3H3,(H,24,28)(H,25,30)(H,26,31)/t14?,15-,16-,17-,18+,21-/m1/s1

> <INCHI_KEY>
VJXBYUITQBTTQM-YIRSYDPWSA-N

> <FORMULA>
C23H37N3O6S3

> <MOLECULAR_WEIGHT>
547.74

> <EXACT_MASS>
547.184449445

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.768105453058844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5S,6R,9S,20R)-6-(butan-2-yl)-5,8,18,21-tetrahydroxy-20-[2-(methylsulfanyl)ethyl]-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
-3.216225914002096

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
-6.513447676036097

> <JCHEM_PKA_STRONGEST_ACIDIC>
-9.863640547152002

> <JCHEM_PKA_STRONGEST_BASIC>
15.64313133033684

> <JCHEM_POLAR_SURFACE_AREA>
144.3

> <JCHEM_REFRACTIVITY>
143.54169999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S,6R,9S,20R)-5,8,18,21-tetrahydroxy-20-[2-(methylsulfanyl)ethyl]-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      10.653  -4.222   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.736  -1.143   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.515   6.817   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.341  -3.417   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.373  -1.756   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.815  -2.866   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.010  -0.148   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.196   5.135   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.472  -2.776   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.663   5.276   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.760  -0.745   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.693  -2.918   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.659   0.976   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.382  -1.877   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.883  -0.212   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.840   3.736   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.658   2.199   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.208  -2.391   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.111   0.991   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.058  -2.853   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.070  -1.071   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.421   3.684   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.195   1.781   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       1.829   2.475   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       5.984   3.604   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       8.873   0.323   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0       8.156  -3.604   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.348   1.483   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       3.410  -4.250   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.486   5.223   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.188   2.958   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.832  -1.513   0.000  0.00  0.00           O+0
HETATM   33  S   UNK     0       0.019   6.675   0.000  0.00  0.00           S+0
HETATM   34  S   UNK     0       3.914  -1.668   0.000  0.00  0.00           S+0
HETATM   35  S   UNK     0       4.888  -0.406   0.000  0.00  0.00           S+0
HETATM   36  H   UNK     0      10.695  -2.683   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.153   0.658   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.692   5.019   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       7.644   3.382   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       6.259  -1.177   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       6.758  -0.266   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   14                                                            
CONECT    3   33                                                            
CONECT    4    1   14                                                       
CONECT    5    6    7                                                       
CONECT    6    5    9                                                       
CONECT    7    5   15                                                       
CONECT    8   10   16                                                       
CONECT    9    6   34                                                       
CONECT   10    8   33                                                       
CONECT   11   15   19                                                       
CONECT   12   18   20                                                       
CONECT   13   17   35                                                       
CONECT   14    2    4   21   36                                             
CONECT   15    7   11   32   37                                             
CONECT   16    8   22   24   38                                             
CONECT   17   13   23   25   39                                             
CONECT   18   12   21   27   40                                             
CONECT   19   11   24   28                                                  
CONECT   20   12   29   32                                                  
CONECT   21   14   18   26   41                                             
CONECT   22   16   25   30                                                  
CONECT   23   17   26   31                                                  
CONECT   24   16   19                                                       
CONECT   25   17   22                                                       
CONECT   26   21   23                                                       
CONECT   27   18                                                            
CONECT   28   19                                                            
CONECT   29   20                                                            
CONECT   30   22                                                            
CONECT   31   23                                                            
CONECT   32   15   20                                                       
CONECT   33    3   10                                                       
CONECT   34    9   35                                                       
CONECT   35   13   34                                                       
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   18                                                            
CONECT   41   21                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   84    0
END

Synonyms

Not Available

Molecular Formula

C₂₃H₃₇N₃O₆S₃

Average Mass

547.74

Monoisotopic Mass

547.184449445

IUPAC Name

(1S,5S,6R,9S,20R)-6-(butan-2-yl)-5,8,18,21-tetrahydroxy-20-[2-(methylsulfanyl)ethyl]-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one

Traditional Name

(1S,5S,6R,9S,20R)-5,8,18,21-tetrahydroxy-20-[2-(methylsulfanyl)ethyl]-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one

CAS Registry Number

Not Available

SMILES

[H]C(C)(CC)[C@@]1([H])N=C(O)[C@@]2([H])CSSCCC=C[C@]([H])(CC(O)=N[C@]([H])(CCSC)C(O)=N2)OC(=O)C[C@]1([H])O

InChI Identifier

InChI=1S/C23H37N3O6S3/c1-4-14(2)21-18(27)12-20(29)32-15-7-5-6-9-34-35-13-17(23(31)26-21)25-22(30)16(8-10-33-3)24-19(28)11-15/h5,7,14-18,21,27H,4,6,8-13H2,1-3H3,(H,24,28)(H,25,30)(H,26,31)/t14?,15-,16-,17-,18+,21-/m1/s1

InChI Key

VJXBYUITQBTTQM-YIRSYDPWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Cyclic depsipeptide
Macrolide lactam
Macrolide
Macrolactam
Alpha-amino acid or derivatives
Secondary carboxylic acid amide
Secondary alcohol
Organic disulfide
Lactone
Lactam
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Dialkylthioether
Sulfenyl compound
Thioether
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	2.22	ALOGPS
logP	-3.2	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	-9.9	ChemAxon
pKa (Strongest Basic)	15.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	144.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	143.54 m³·mol⁻¹	ChemAxon
Polarizability	55.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	145.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	53.8
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	557.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	520.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	454.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	166.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2301.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	89.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	371.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	312.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	188.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	149.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	153.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	8.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	215.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	124.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	358.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1274.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1128.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Thailandepsin A_TMS_1	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O	standard non polar	2025-10-23	746.895
Gas Chromatography	Thailandepsin A_TMS_2	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O	standard non polar	2025-10-23	1713.82
Gas Chromatography	Thailandepsin A_TMS_3	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O	standard non polar	2025-10-23	2289.22
Gas Chromatography	Thailandepsin A_TMS_4	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1303.56
Gas Chromatography	Thailandepsin A_TMS_5	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O	standard non polar	2025-10-23	1772.77
Gas Chromatography	Thailandepsin A_TMS_6	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O	standard non polar	2025-10-23	3276.26
Gas Chromatography	Thailandepsin A_TMS_7	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2323.34
Gas Chromatography	Thailandepsin A_TMS_8	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O	standard non polar	2025-10-23	2596.76
Gas Chromatography	Thailandepsin A_TMS_9	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2680.1
Gas Chromatography	Thailandepsin A_TMS_10	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1751.14
Gas Chromatography	Thailandepsin A_TMS_11	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O	standard non polar	2025-10-23	2221.22
Gas Chromatography	Thailandepsin A_TMS_12	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1918.27
Gas Chromatography	Thailandepsin A_TMS_13	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1995.33
Gas Chromatography	Thailandepsin A_TMS_14	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1962.59
Gas Chromatography	Thailandepsin A_TMS_15	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2518.0
Gas Chromatography	Thailandepsin A_TMS_1	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O	standard polar	2025-10-23	1396.23
Gas Chromatography	Thailandepsin A_TMS_2	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O	standard polar	2025-10-23	2218.79
Gas Chromatography	Thailandepsin A_TMS_3	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O	standard polar	2025-10-23	2133.31
Gas Chromatography	Thailandepsin A_TMS_4	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2412.17
Gas Chromatography	Thailandepsin A_TMS_5	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O	standard polar	2025-10-23	2649.03
Gas Chromatography	Thailandepsin A_TMS_6	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O	standard polar	2025-10-23	2483.85
Gas Chromatography	Thailandepsin A_TMS_7	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2419.05
Gas Chromatography	Thailandepsin A_TMS_8	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O	standard polar	2025-10-23	1525.04
Gas Chromatography	Thailandepsin A_TMS_9	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2865.21
Gas Chromatography	Thailandepsin A_TMS_10	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1486.91
Gas Chromatography	Thailandepsin A_TMS_11	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O	standard polar	2025-10-23	1448.35
Gas Chromatography	Thailandepsin A_TMS_12	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	-159.24
Gas Chromatography	Thailandepsin A_TMS_13	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1514.31
Gas Chromatography	Thailandepsin A_TMS_14	CCC(C)[C@H]1N=C(O)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	4265.36
Gas Chromatography	Thailandepsin A_TMS_15	CCC(C)[C@H]1N=C(O[Si](C)(C)C)[C@H]2CSSCCC=C[C@H](CC(O[Si](C)(C)C)=N[C@H](CCSC)C(O[Si](C)(C)C)=N2)OC(=O)C[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1709.84

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1		Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50925571

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Thailandepsin A (MMDBc0016145)

MOL for #<Metabolite:0x00007f9adb391ef8>

3D MOL for #<Metabolite:0x00007f9adb391ef8>

3D SDF for #<Metabolite:0x00007f9adb391ef8>

3D-SDF for #<Metabolite:0x00007f9adb391ef8>

PDB for #<Metabolite:0x00007f9adb391ef8>

3D PDB for #<Metabolite:0x00007f9adb391ef8>

SMILES for #<Metabolite:0x00007f9adb391ef8>

INCHI for #<Metabolite:0x00007f9adb391ef8>

Structure for #<Metabolite:0x00007f9adb391ef8>

3D Structure for #<Metabolite:0x00007f9adb391ef8>