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Showing metabocard for Ethionamide (HMDB0014747)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2023-02-21 17:18:16 UTC
HMDB IDHMDB0014747
Secondary Accession Numbers
  • HMDB14747
Metabolite Identification
Common NameEthionamide
DescriptionEthionamide is only found in individuals that have used or taken this drug. It is a second-line antitubercular agent that inhibits mycolic acid synthesis. It also may be used for treatment of leprosy. (From Smith and Reynard, Textbook of Pharmacology, 1992, p868)Ethionamide may be bacteriostatic or bactericidal in action, depending on the concentration of the drug attained at the site of infection and the susceptibility of the infecting organism. Ethionamide, like prothionamide and pyrazinamide, is a nicotinic acid derivative related to isoniazid. It is thought that ethionamide undergoes intracellular modification and acts in a similar fashion to isoniazid. Isoniazid inhibits the synthesis of mycoloic acids, an essential component of the bacterial cell wall. Specifically isoniazid inhibits InhA, the enoyl reductase from Mycobacterium tuberculosis, by forming a covalent adduct with the NAD cofactor. It is the INH-NAD adduct that acts as a slow, tight-binding competitive inhibitor of InhA.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014747 (Ethionamide)

609
  Mrv0541 02231214482D          

 11 11  0  0  0  0            999 V2000
    2.3644    1.6005    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.2870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.6005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0  0  0  0
  2  5  2  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
Download

3D MOL for HMDB0014747 (Ethionamide)

HMDB0014747
     RDKit          3D
Ethionamide
 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.9689   -0.2791   -0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1913   -0.0940    0.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8940    0.5295    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1504   -0.3277    0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4111    0.1552   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5025   -0.7474   -0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6337   -1.9797    0.1639 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6204   -0.4091   -1.6509 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570    1.5318   -0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4908    2.3457    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7004    1.8463    0.3957 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6789   -1.2785   -0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0526   -0.2147   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6228    0.4618   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156   -1.0902    1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7541    0.5334    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0575   -1.4063    0.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7960   -2.5540    0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590   -2.4138    0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5122    1.9505   -0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    3.4404    0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  4 17  1  0
  7 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
M  END
Download

3D SDF for HMDB0014747 (Ethionamide)

609
  Mrv0541 02231214482D          

 11 11  0  0  0  0            999 V2000
    2.3644    1.6005    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.2870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.6005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0  0  0  0
  2  5  2  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014747

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=NC=CC(=C1)C(N)=S

> <INCHI_IDENTIFIER>
InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)

> <INCHI_KEY>
AEOCXXJPGCBFJA-UHFFFAOYSA-N

> <FORMULA>
C8H10N2S

> <MOLECULAR_WEIGHT>
166.243

> <EXACT_MASS>
166.05646902

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
17.98666589320431

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-ethylpyridine-4-carbothioamide

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
1.3279892836666667

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.89396990677615

> <JCHEM_PKA_STRONGEST_BASIC>
5.003405417249389

> <JCHEM_POLAR_SURFACE_AREA>
38.91

> <JCHEM_REFRACTIVITY>
50.1888

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethionamide

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0014747 (Ethionamide)

HMDB0014747
     RDKit          3D
Ethionamide
 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.9689   -0.2791   -0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1913   -0.0940    0.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8940    0.5295    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1504   -0.3277    0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4111    0.1552   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5025   -0.7474   -0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6337   -1.9797    0.1639 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6204   -0.4091   -1.6509 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570    1.5318   -0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4908    2.3457    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7004    1.8463    0.3957 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6789   -1.2785   -0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0526   -0.2147   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6228    0.4618   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156   -1.0902    1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7541    0.5334    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0575   -1.4063    0.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7960   -2.5540    0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590   -2.4138    0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5122    1.9505   -0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    3.4404    0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  4 17  1  0
  7 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
M  END
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PDB for HMDB0014747 (Ethionamide)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 609                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.414   2.988   0.000  0.00  0.00           S+0
HETATM    2  N   UNK     0       5.747  -2.402   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       7.081   2.988   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.080  -2.402   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  -1.632   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -0.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747   0.678   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080  -3.942   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -0.092   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -1.632   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   2.218   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2    5   10                                                       
CONECT    3   11                                                            
CONECT    4    5    8                                                       
CONECT    5    2    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    9   11                                                  
CONECT    8    4                                                            
CONECT    9    7   10                                                       
CONECT   10    2    9                                                       
CONECT   11    1    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0014747 (Ethionamide)

COMPND    HMDB0014747
HETATM    1  C1  UNL     1      -2.969  -0.279  -0.462  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.191  -0.094   0.841  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.894   0.529   0.460  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.150  -0.328   0.161  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.411   0.155  -0.208  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.502  -0.747  -0.520  1.00  0.00           C  
HETATM    7  N1  UNL     1       2.634  -1.980   0.164  1.00  0.00           N  
HETATM    8  S1  UNL     1       3.620  -0.409  -1.651  1.00  0.00           S  
HETATM    9  C7  UNL     1       1.557   1.532  -0.259  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.491   2.346   0.046  1.00  0.00           C  
HETATM   11  N2  UNL     1      -0.700   1.846   0.396  1.00  0.00           N  
HETATM   12  H1  UNL     1      -2.679  -1.278  -0.884  1.00  0.00           H  
HETATM   13  H2  UNL     1      -4.053  -0.215  -0.254  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.623   0.462  -1.215  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.016  -1.090   1.272  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.754   0.533   1.559  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.058  -1.406   0.195  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.796  -2.554   0.479  1.00  0.00           H  
HETATM   19  H8  UNL     1       3.559  -2.414   0.408  1.00  0.00           H  
HETATM   20  H9  UNL     1       2.512   1.951  -0.539  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.588   3.440   0.011  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4    4   11
CONECT    4    5   17
CONECT    5    6    9    9
CONECT    6    7    8    8
CONECT    7   18   19
CONECT    9   10   20
CONECT   10   11   11   21
END
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SMILES for HMDB0014747 (Ethionamide)

CCC1=NC=CC(=C1)C(N)=S
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INCHI for HMDB0014747 (Ethionamide)

InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC8H10N2S
Average Molecular Weight166.243
Monoisotopic Molecular Weight166.05646902
IUPAC Name2-ethylpyridine-4-carbothioamide
Traditional Nameethionamide
CAS Registry Number536-33-4
SMILES
CCC1=NC=CC(=C1)C(N)=S
InChI Identifier
InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)
InChI KeyAEOCXXJPGCBFJA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassNot Available
Direct ParentPyridines and derivatives
Alternative Parents
Substituents
  • Pyridine
  • Heteroaromatic compound
  • Thioamide
  • Azacycle
  • Thiocarboxylic acid amide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Thiocarbonyl group
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point163 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.84 g/LNot Available
LogP0.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00609 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00609 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00609
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2041901
KEGG Compound IDC07665
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthionamide
METLIN IDNot Available
PubChem Compound2761171
PDB IDNot Available
ChEBI ID4885
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available