ECMDB: 2-Mercapto-1-methylimidazole (ECMDB21406) (M2MDB001801)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References XML

Record Information

Version

2.0

Creation Date

2012-08-03 15:09:30 -0600

Update Date

2015-06-03 17:21:25 -0600

Secondary Accession Numbers

ECMDB21406

Identification

Name:

2-Mercapto-1-methylimidazole

Description

2-Mercapto-1-methylimidazole is a thioureylene antithyroid agent that inhibits the formation of thyroid hormones by interfering with the incorporation of iodine into tyrosyl residues of thyroglobulin. This is done by interfering with the oxidation of iodide ion and iodotyrosyl groups through inhibition of the peroxidase enzyme. [PubChem]

Structure

MOL SDF PDB SMILES InChI

Synonyms:

1,3-Dihydro-1-methyl-2H-imidazole-2-thione
1-Methyl-1,3-dihydro-2H-imidazole-2-thione
1-Methyl-1,3-dihydroimidazole-2-thione
1-Methyl-2-imidazolethiol
1-Methyl-2-mercapto-Imidazole
1-Methyl-2-mercaptoimidazole
1-Methyl-4-Imidazoline-2-thione
1-Methyl-Imidazole-2-thio
1-Methyl-Imidazole-2-thiol
1-Methylimidazole-2(3H)-thione
1-Methylimidazole-2-thiol
1-Methylimidazole-2-thione
1-Metylo 2 merkaptoimidazolem
2-Mercaptomethylimidazole
Basolan
Danantizol
Favistan
Frentirox
Mercaptazole
Mercasolyl
Mercazole
Mercazolyl
Merkastan
Merkazolil
Metazolo
Methamazole
Methiamazole
Methimazol
Methimazole
Methylmercaptoimidazole
Metizol
Metothyrin
Metothyrine
Metotirin
N-Methyl-2-mercaptoimidazole
Strumazol
Strumazole
Tapazole
Tapuzole
Thacapzol
Thiamazol
Thiamazole
Thiamazolum
Thimazole
Thycapsol
Thycapzol
Thymidazol
Thymidazole
Tiamazol
USAF EL-30

Chemical Formula:

C₄H₆N₂S

Weight:

Average: 114.169
Monoisotopic: 114.025168892

InChI Key:

PMRYVIKBURPHAH-UHFFFAOYSA-N

InChI:

InChI=1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)

CAS number:

60-56-0

IUPAC Name:

1-methyl-2,3-dihydro-1H-imidazole-2-thione

Traditional IUPAC Name:

methimazole

SMILES:

CN1C=CNC1=S

Chemical Taxonomy

Description

belongs to the class of organic compounds known as imidazolethiones. These are aromatic compounds containing an imidazole ring which bears a thioketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolines

Sub Class

Imidazolines

Direct Parent

Imidazolethiones

Alternative Parents

Substituents

N-substituted imidazole
Imidazole-2-thione
Heteroaromatic compound
Imidazole
Azole
Thiourea
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:50673 )
thioureas (CHEBI:50673 )
a small molecule (CPD-11282 )

Physical Properties

State:

Solid

Charge:

Melting point:

146 °C

Experimental Properties:

Property	Value	Source
LogP:	-0.34	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	11.3 g/L	ALOGPS
logP	-0.38	ALOGPS
logP	0.75	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	10.41	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.27 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.23 m³·mol⁻¹	ChemAxon
Polarizability	11.64 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
186± 0 uM	BW25113	48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco	Stationary Phase, glucose limited	Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h	37 oC	PMID: 17379776

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9400000000-2a587b1850e13e97c2cf	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-066r-8900000000-9230df83b87c13377bfb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0900000000-275f9771b8d1d7486052	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0900000000-1763fdc1a812fa765250	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0900000000-78877e6d65fda61a0e67	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-1900000000-c979e7cdbceb656b6a1e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-1900000000-1447e5774eda5dc3fe26	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-066r-9300000000-41d253a513ee17fed774	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-11684a341cebaa28c427	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a60-9000000000-7637560408e70990bc27	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - -1V, Positive	splash10-066r-8900000000-9230df83b87c13377bfb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-374ccd1b69e853438841	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-c6da240ee4f95cf882f2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-275f9771b8d1d7486052	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-1763fdc1a812fa765250	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-fb071a5f16c608333fba	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-78877e6d65fda61a0e67	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-3e543dd0166f52789fcd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0900-9300000000-90c58541a936c6fdd275	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-9a1c61f319838c2ebce9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-022c-9200000000-3ef9cd647246e770cc65	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03k9-9800000000-4cd0298581c2529c50e7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-7f5fe02e4938bb18ff53	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-810e7a010dd805f3251d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-e88140069cbfa61f9c51	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-3969b3a3102e9214d562	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	50673
HMDB ID	HMDB0014901
Pubchem Compound ID	1349907
Kegg ID	C07190
ChemSpider ID	1131173
Wikipedia ID	Methimazole
BioCyc ID	Not Available
Ligand Expo	MMZ

2-Mercapto-1-methylimidazole (ECMDB21406) (M2MDB001801)

Structure for #<Compound:0xa720d3f0>