SML1151
Thiophene-4
≥98% (HPLC)
Synonym(s):
5-(Aminocarbonyl)-4-methyl-2-[(pentafluorobenzoyl)amino]-3-thiophenecarboxylic acid ethyl ester, TP4
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About This Item
Empirical Formula (Hill Notation):
C16H11F5N2O4S
CAS Number:
Molecular Weight:
422.33
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Quality Segment
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 20 mg/mL, clear
storage temp.
2-8°C
SMILES string
NC(C1=C(C)C(C(OCC)=O)=C(NC(C2=C(F)C(F)=C(F)C(F)=C2F)=O)S1)=O
InChI
1S/C16H11F5N2O4S/c1-3-27-16(26)5-4(2)12(13(22)24)28-15(5)23-14(25)6-7(17)9(19)11(21)10(20)8(6)18/h3H2,1-2H3,(H2,22,24)(H,23,25)
InChI key
ANCBHJKEYPZCTE-UHFFFAOYSA-N
Biochem/physiol Actions
Thiophene-4 (TP4) is an inhibitor of polyketide synthase 13 (Pks13), which plays a critical role in the biosynthesis of mycolic acid, an essential component of the cell wall in M. tuberculosis, and is a potential new target for tuberculosis treatment.
Thiophene-4 (TP4) is an inhibitor of polyketide synthase 13 (Pks13), which plays a critical role in the biosynthesis of mycolic acid, an essential component of the cell wall in M. tuberculosis, and is a potential new target for tuberculosis treatment. TP4 inhibits FadD32-dependent loading of the mycolic acid precursor meromycoloyl chain onto acyl carrier protein (ACP) domains located at the N terminus of Pks13, preventing synthesis of mycolic acid and resulting in mycobacterial cell death. TP4 bacteriosidal activity is equivalent to treatment with the first-line drug isoniazid, and enhances its activity, but is less likely to cause resistance. The minimal inhibitory concentration (MIC) values of TP4 against drug-susceptible multidrug-resistant M. tuberculosis strains is approximately 500 nM.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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