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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:39:20 UTC

Update Date

2022-11-23 22:29:20 UTC

HMDB ID

HMDB0259177

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Trichostatin A

Description

N-hydroxy7-[4-(dimethylamino)phenyl]-4,6-dimethyl-7-oxohepta-2,4-dienimidic acid belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review very few articles have been published on N-hydroxy7-[4-(dimethylamino)phenyl]-4,6-dimethyl-7-oxohepta-2,4-dienimidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Trichostatin a is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Trichostatin A is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0259177
     RDKit          3D
trichostatin A
 44 44  0  0  0  0  0  0  0  0999 V2000
    3.7478   -1.7050   -0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9279   -0.6744    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217    0.5347    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9222    0.6308    0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5878    1.9301    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6904    2.7588    1.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9448    1.9890    0.7671 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2185    2.0590    0.7450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6062   -0.6821    0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776   -1.8213   -0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3440   -2.8098    0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2950   -1.2873   -1.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1764   -1.3965   -2.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211   -0.6114   -0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655    0.1285   -1.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4755    0.6848   -1.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0354    0.5327   -0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3025    1.0655    0.1412 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4525    0.1741    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5736    2.4488    0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -0.1809    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0926   -0.7444    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5526   -2.0894    0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3544   -1.2758   -1.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2206   -2.6132   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0801    1.3653    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5267   -0.1459   -0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9391    3.2666    1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5941    1.8079   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1118    0.1034    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4595   -2.3492   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235   -2.3348    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0893   -3.6941    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6170   -3.2804    0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8653    0.2688   -2.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0601    1.2776   -2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4693   -0.4990    0.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3996    0.7373   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3093   -0.4393   -0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4633    2.5425    1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8011    2.9547   -0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7186    2.9731    0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7642   -0.3144    1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466   -1.2853    1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  2  9  2  3
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 17 21  1  0
 21 22  2  0
 22 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
M  END


  Mrv0541 04121512082D          

 22 22  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  4  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259177

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C=C(C)C=CC(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O3/c1-12(5-10-16(20)18-22)11-13(2)17(21)14-6-8-15(9-7-14)19(3)4/h5-11,13,22H,1-4H3,(H,18,20)

> <INCHI_KEY>
RTKIYFITIVXBLE-UHFFFAOYSA-N

> <FORMULA>
C17H22N2O3

> <MOLECULAR_WEIGHT>
302.374

> <EXACT_MASS>
302.163042576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.99488725686492

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.4096309773333324

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.09038690351591

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.5673114677343

> <JCHEM_PKA_STRONGEST_BASIC>
3.360376109059752

> <JCHEM_POLAR_SURFACE_AREA>
69.64

> <JCHEM_REFRACTIVITY>
90.2389

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259177
     RDKit          3D
trichostatin A
 44 44  0  0  0  0  0  0  0  0999 V2000
    3.7478   -1.7050   -0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9279   -0.6744    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217    0.5347    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9222    0.6308    0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5878    1.9301    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6904    2.7588    1.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9448    1.9890    0.7671 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2185    2.0590    0.7450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6062   -0.6821    0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776   -1.8213   -0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3440   -2.8098    0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2950   -1.2873   -1.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1764   -1.3965   -2.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211   -0.6114   -0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655    0.1285   -1.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4755    0.6848   -1.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0354    0.5327   -0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3025    1.0655    0.1412 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4525    0.1741    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5736    2.4488    0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -0.1809    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0926   -0.7444    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5526   -2.0894    0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3544   -1.2758   -1.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2206   -2.6132   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0801    1.3653    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5267   -0.1459   -0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9391    3.2666    1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5941    1.8079   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1118    0.1034    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4595   -2.3492   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235   -2.3348    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0893   -3.6941    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6170   -3.2804    0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8653    0.2688   -2.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0601    1.2776   -2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4693   -0.4990    0.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3996    0.7373   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3093   -0.4393   -0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4633    2.5425    1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8011    2.9547   -0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7186    2.9731    0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7642   -0.3144    1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466   -1.2853    1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  2  9  2  3
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 17 21  1  0
 21 22  2  0
 22 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       4.001  11.550   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       4.001  13.090   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0259177
HETATM    1  C1  UNL     1       3.748  -1.705  -0.607  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.928  -0.674   0.035  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.622   0.535   0.449  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.922   0.631   0.360  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.588   1.930   0.796  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.690   2.759   1.133  1.00  0.00           O  
HETATM    7  N1  UNL     1       6.945   1.989   0.767  1.00  0.00           N  
HETATM    8  O2  UNL     1       8.218   2.059   0.745  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.606  -0.682   0.189  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.778  -1.821  -0.334  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.344  -2.810   0.663  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.295  -1.287  -1.186  1.00  0.00           C  
HETATM   13  O3  UNL     1      -0.176  -1.396  -2.479  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.521  -0.611  -0.794  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.265   0.129  -1.720  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.475   0.685  -1.423  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.035   0.533  -0.140  1.00  0.00           C  
HETATM   18  N2  UNL     1      -5.303   1.065   0.141  1.00  0.00           N  
HETATM   19  C14 UNL     1      -6.452   0.174   0.087  1.00  0.00           C  
HETATM   20  C15 UNL     1      -5.574   2.449   0.465  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.336  -0.181   0.787  1.00  0.00           C  
HETATM   22  C17 UNL     1      -2.093  -0.744   0.458  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.553  -2.089   0.119  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.354  -1.276  -1.431  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.221  -2.613  -0.889  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.080   1.365   0.859  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.527  -0.146  -0.002  1.00  0.00           H  
HETATM   28  H6  UNL     1       6.939   3.267   1.223  1.00  0.00           H  
HETATM   29  H7  UNL     1       8.594   1.808  -0.155  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.112   0.103   0.682  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.460  -2.349  -1.053  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.323  -2.335   1.662  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.089  -3.694   0.735  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.617  -3.280   0.374  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.865   0.269  -2.706  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.060   1.278  -2.128  1.00  0.00           H  
HETATM   37  H15 UNL     1      -6.469  -0.499   0.998  1.00  0.00           H  
HETATM   38  H16 UNL     1      -7.400   0.737  -0.018  1.00  0.00           H  
HETATM   39  H17 UNL     1      -6.309  -0.439  -0.832  1.00  0.00           H  
HETATM   40  H18 UNL     1      -6.463   2.543   1.117  1.00  0.00           H  
HETATM   41  H19 UNL     1      -5.801   2.955  -0.494  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.719   2.973   0.927  1.00  0.00           H  
HETATM   43  H21 UNL     1      -3.764  -0.314   1.774  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.647  -1.285   1.267  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    9    9
CONECT    3    4    4   26
CONECT    4    5   27
CONECT    5    6    6    7
CONECT    7    8   28
CONECT    8   29
CONECT    9   10   30
CONECT   10   11   12   31
CONECT   11   32   33   34
CONECT   12   13   13   14
CONECT   14   15   15   22
CONECT   15   16   35
CONECT   16   17   17   36
CONECT   17   18   21
CONECT   18   19   20
CONECT   19   37   38   39
CONECT   20   40   41   42
CONECT   21   22   22   43
CONECT   22   44
END

HMDB0259177
     RDKit          3D
trichostatin A
 44 44  0  0  0  0  0  0  0  0999 V2000
    3.7478   -1.7050   -0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9279   -0.6744    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217    0.5347    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9222    0.6308    0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5878    1.9301    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6904    2.7588    1.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9448    1.9890    0.7671 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2185    2.0590    0.7450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6062   -0.6821    0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776   -1.8213   -0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3440   -2.8098    0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2950   -1.2873   -1.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1764   -1.3965   -2.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211   -0.6114   -0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655    0.1285   -1.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4755    0.6848   -1.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0354    0.5327   -0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3025    1.0655    0.1412 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4525    0.1741    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5736    2.4488    0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -0.1809    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0926   -0.7444    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5526   -2.0894    0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3544   -1.2758   -1.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2206   -2.6132   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0801    1.3653    0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5267   -0.1459   -0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9391    3.2666    1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5941    1.8079   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1118    0.1034    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4595   -2.3492   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235   -2.3348    1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0893   -3.6941    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6170   -3.2804    0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8653    0.2688   -2.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0601    1.2776   -2.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4693   -0.4990    0.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3996    0.7373   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3093   -0.4393   -0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4633    2.5425    1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8011    2.9547   -0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7186    2.9731    0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7642   -0.3144    1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466   -1.2853    1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  2  9  2  3
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 17 21  1  0
 21 22  2  0
 22 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Hydroxy7-[4-(dimethylamino)phenyl]-4,6-dimethyl-7-oxohepta-2,4-dienimidate	Generator

Chemical Formula

C₁₇H₂₂N₂O₃

Average Molecular Weight

302.374

Monoisotopic Molecular Weight

302.163042576

IUPAC Name

7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide

Traditional Name

7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide

CAS Registry Number

Not Available

SMILES

CC(C=C(C)C=CC(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C

InChI Identifier

InChI=1S/C17H22N2O3/c1-12(5-10-16(20)18-22)11-13(2)17(21)14-6-8-15(9-7-14)19(3)4/h5-11,13,22H,1-4H3,(H,18,20)

InChI Key

RTKIYFITIVXBLE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Phenylpropane
Benzoyl
Tertiary aliphatic/aromatic amine
Aniline or substituted anilines
Dialkylarylamine
Aryl alkyl ketone
Monocyclic benzene moiety
Benzenoid
Tertiary amine
Amine
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	2.36	ALOGPS
logP	2.41	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.57	ChemAxon
pKa (Strongest Basic)	3.36	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90.24 m³·mol⁻¹	ChemAxon
Polarizability	33.99 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	171.596	30932474
DeepCCS	[M-H]-	169.238	30932474
DeepCCS	[M-2H]-	202.919	30932474
DeepCCS	[M+Na]+	178.147	30932474
AllCCS	[M+H]+	175.1	32859911
AllCCS	[M+H-H2O]+	171.9	32859911
AllCCS	[M+NH4]+	178.2	32859911
AllCCS	[M+Na]+	179.1	32859911
AllCCS	[M-H]-	176.3	32859911
AllCCS	[M+Na-2H]-	176.9	32859911
AllCCS	[M+HCOO]-	177.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.84 minutes	32390414
Predicted by Siyang on May 30, 2022	14.1825 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.5 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2468.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	310.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	471.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	534.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1283.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	447.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1419.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	386.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	373.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	257.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	257.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trichostatin A	CC(C=C(C)C=CC(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C	4021.8	Standard polar	33892256
trichostatin A	CC(C=C(C)C=CC(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C	2738.1	Standard non polar	33892256
trichostatin A	CC(C=C(C)C=CC(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C	3088.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trichostatin A,1TMS,isomer #1	CC(C=CC(=O)N(O)[Si](C)(C)C)=CC(C)C(=O)C1=CC=C(N(C)C)C=C1	2983.1	Semi standard non polar	33892256
trichostatin A,1TMS,isomer #1	CC(C=CC(=O)N(O)[Si](C)(C)C)=CC(C)C(=O)C1=CC=C(N(C)C)C=C1	2760.6	Standard non polar	33892256
trichostatin A,1TMS,isomer #1	CC(C=CC(=O)N(O)[Si](C)(C)C)=CC(C)C(=O)C1=CC=C(N(C)C)C=C1	3425.9	Standard polar	33892256
trichostatin A,1TBDMS,isomer #1	CC(C=CC(=O)N(O)[Si](C)(C)C(C)(C)C)=CC(C)C(=O)C1=CC=C(N(C)C)C=C1	3210.0	Semi standard non polar	33892256
trichostatin A,1TBDMS,isomer #1	CC(C=CC(=O)N(O)[Si](C)(C)C(C)(C)C)=CC(C)C(=O)C1=CC=C(N(C)C)C=C1	2959.0	Standard non polar	33892256
trichostatin A,1TBDMS,isomer #1	CC(C=CC(=O)N(O)[Si](C)(C)C(C)(C)C)=CC(C)C(=O)C1=CC=C(N(C)C)C=C1	3446.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Trichostatin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1930000000-4083471e97d0edded83b	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trichostatin A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5562

PDB ID

Not Available

ChEBI ID

91570

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Trichostatin A (HMDB0259177)

MOL for HMDB0259177 (Trichostatin A)

3D MOL for HMDB0259177 (Trichostatin A)

3D SDF for HMDB0259177 (Trichostatin A)

3D-SDF for HMDB0259177 (Trichostatin A)

PDB for HMDB0259177 (Trichostatin A)

3D PDB for HMDB0259177 (Trichostatin A)

SMILES for HMDB0259177 (Trichostatin A)

INCHI for HMDB0259177 (Trichostatin A)

Structure for HMDB0259177 (Trichostatin A)

3D Structure for HMDB0259177 (Trichostatin A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra