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Showing metabocard for Carbimazole (HMDB0014533)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:13 UTC
HMDB IDHMDB0014533
Secondary Accession Numbers
  • HMDB14533
Metabolite Identification
Common NameCarbimazole
DescriptionCarbimazole is only found in individuals that have used or taken this drug. It is an imidazole antithyroid agent. Carbimazole is metabolized to methimazole, which is responsible for the antithyroid activity. [PubChem]Carbimazole is an aitithyroid agent that decreases the uptake and concentration of inorganic iodine by thyroid, it also reduces the formation of di-iodotyrosine and thyroxine. Once converted to its active form of methimazole, it prevents the thyroid peroxidase enzyme from coupling and iodinating the tyrosine residues on thyroglobulin, hence reducing the production of the thyroid hormones T3 and T4.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014533 (Carbimazole)

389
  Mrv0541 02231214382D          

 12 12  0  0  0  0            999 V2000
    4.5311    0.4990    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.9685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    1.5386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    0.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4115    0.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666    1.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9764    2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3 10  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  7  8  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
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3D MOL for HMDB0014533 (Carbimazole)

HMDB0014533
     RDKit          3D
Carbimazole
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.7419    0.2963   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1546   -1.0908   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -1.0503    0.2992 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9090   -0.2850   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3458    0.3658   -1.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844   -0.2098   -0.0677 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1123   -0.8301    0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4444   -0.4553    0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6196    0.3860   -0.1604 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8814    1.0096   -0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4047    0.5200   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0857    1.4495   -2.0282 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454    0.1931    0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6482    0.8308   -0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2641    0.8606    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328   -1.8122    0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1665   -1.3959   -1.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759   -1.5040    1.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481   -0.7760    1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7808    1.4087   -1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7067    0.2407   -0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1512    1.8483    0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11  6  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  7 18  1  0
  8 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
M  END
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3D SDF for HMDB0014533 (Carbimazole)

389
  Mrv0541 02231214382D          

 12 12  0  0  0  0            999 V2000
    4.5311    0.4990    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.9685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    1.5386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    0.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4115    0.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666    1.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9764    2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3 10  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  7  8  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014533

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)N1C=CN(C)C1=S

> <INCHI_IDENTIFIER>
InChI=1S/C7H10N2O2S/c1-3-11-7(10)9-5-4-8(2)6(9)12/h4-5H,3H2,1-2H3

> <INCHI_KEY>
CFOYWRHIYXMDOT-UHFFFAOYSA-N

> <FORMULA>
C7H10N2O2S

> <MOLECULAR_WEIGHT>
186.232

> <EXACT_MASS>
186.046298264

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.706131643135368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazole-1-carboxylate

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
1.3485111993333334

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9999999999999996

> <JCHEM_POLAR_SURFACE_AREA>
32.78

> <JCHEM_REFRACTIVITY>
49.170300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carbimazole

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0014533 (Carbimazole)

HMDB0014533
     RDKit          3D
Carbimazole
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.7419    0.2963   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1546   -1.0908   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -1.0503    0.2992 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9090   -0.2850   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3458    0.3658   -1.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844   -0.2098   -0.0677 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1123   -0.8301    0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4444   -0.4553    0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6196    0.3860   -0.1604 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8814    1.0096   -0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4047    0.5200   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0857    1.4495   -2.0282 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454    0.1931    0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6482    0.8308   -0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2641    0.8606    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328   -1.8122    0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1665   -1.3959   -1.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759   -1.5040    1.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481   -0.7760    1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7808    1.4087   -1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7067    0.2407   -0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1512    1.8483    0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11  6  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  7 18  1  0
  8 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
M  END
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PDB for HMDB0014533 (Carbimazole)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 389                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       8.458   0.931   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       4.414  -1.808   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.081  -1.808   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.518   2.872   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.748   0.502   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.993   1.407   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.501   1.407   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.978   2.872   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.423   4.118   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -1.038   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -3.348   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -4.118   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2   10   11                                                       
CONECT    3   10                                                            
CONECT    4    6    8    9                                                  
CONECT    5    6    7   10                                                  
CONECT    6    1    4    5                                                  
CONECT    7    5    8                                                       
CONECT    8    4    7                                                       
CONECT    9    4                                                            
CONECT   10    2    3    5                                                  
CONECT   11    2   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0014533 (Carbimazole)

COMPND    HMDB0014533
HETATM    1  C1  UNL     1       3.742   0.296  -0.019  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.155  -1.091  -0.084  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.787  -1.050   0.299  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.909  -0.285  -0.414  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.346   0.366  -1.397  1.00  0.00           O  
HETATM    6  N1  UNL     1      -0.484  -0.210  -0.068  1.00  0.00           N  
HETATM    7  C4  UNL     1      -1.112  -0.830   0.937  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.444  -0.455   0.875  1.00  0.00           C  
HETATM    9  N2  UNL     1      -2.620   0.386  -0.160  1.00  0.00           N  
HETATM   10  C6  UNL     1      -3.881   1.010  -0.567  1.00  0.00           C  
HETATM   11  C7  UNL     1      -1.405   0.520  -0.721  1.00  0.00           C  
HETATM   12  S1  UNL     1      -1.086   1.450  -2.028  1.00  0.00           S  
HETATM   13  H1  UNL     1       4.845   0.193   0.162  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.648   0.831  -0.987  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.264   0.861   0.785  1.00  0.00           H  
HETATM   16  H4  UNL     1       3.733  -1.812   0.520  1.00  0.00           H  
HETATM   17  H5  UNL     1       3.167  -1.396  -1.161  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.676  -1.504   1.672  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.248  -0.776   1.547  1.00  0.00           H  
HETATM   20  H8  UNL     1      -3.781   1.409  -1.597  1.00  0.00           H  
HETATM   21  H9  UNL     1      -4.707   0.241  -0.585  1.00  0.00           H  
HETATM   22  H10 UNL     1      -4.151   1.848   0.092  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   11
CONECT    7    8    8   18
CONECT    8    9   19
CONECT    9   10   11
CONECT   10   20   21   22
CONECT   11   12   12
END
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SMILES for HMDB0014533 (Carbimazole)

CCOC(=O)N1C=CN(C)C1=S
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INCHI for HMDB0014533 (Carbimazole)

InChI=1S/C7H10N2O2S/c1-3-11-7(10)9-5-4-8(2)6(9)12/h4-5H,3H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC7H10N2O2S
Average Molecular Weight186.232
Monoisotopic Molecular Weight186.046298264
IUPAC Nameethyl 3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazole-1-carboxylate
Traditional Namecarbimazole
CAS Registry Number22232-54-8
SMILES
CCOC(=O)N1C=CN(C)C1=S
InChI Identifier
InChI=1S/C7H10N2O2S/c1-3-11-7(10)9-5-4-8(2)6(9)12/h4-5H,3H2,1-2H3
InChI KeyCFOYWRHIYXMDOT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carbonylimidazoles. These are substituted imidazoles in which the imidazole ring bears a carbonyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentCarbonylimidazoles
Alternative Parents
Substituents
  • Imidazole-1-carbonyl group
  • Imidazole-2-thione
  • N-substituted imidazole
  • Heteroaromatic compound
  • Carbonic acid derivative
  • Thiourea
  • Azacycle
  • Organic nitrogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Point123.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.14 g/LNot Available
LogP0.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available134.362http://allccs.zhulab.cn/database/detail?ID=AllCCS00001095
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00389 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00389 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00389
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28829
KEGG Compound IDC07615
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarbimazole
METLIN IDNot Available
PubChem Compound31072
PDB IDNot Available
ChEBI ID617099
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

Enzymes

Enzyme Details
1. Thyroid peroxidase
General function:
Involved in calcium ion binding
Specific function:
Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name:
TPO
Uniprot ID:
P07202
Molecular weight:
102961.63
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Guilhem I, Massart C, Poirier JY, Maugendre D: Differential evolution of thyroid peroxidase and thyrotropin receptor antibodies in Graves' disease: thyroid peroxidase antibody activity reverts to pretreatment level after carbimazole withdrawal. Thyroid. 2006 Oct;16(10):1041-5. [PubMed:17042691 ]
  3. Magnusson RP, Taurog A, Dorris ML: Mechanism of iodide-dependent catalatic activity of thyroid peroxidase and lactoperoxidase. J Biol Chem. 1984 Jan 10;259(1):197-205. [PubMed:6706930 ]
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Enzyme Details
2. Cytochrome P450 19A1
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
References
  1. Ayub M, Levell MJ: Structure-activity relationships of the inhibition of human placental aromatase by imidazole drugs including ketoconazole. J Steroid Biochem. 1988 Jul;31(1):65-72. [PubMed:3398530 ]