Thielavin P
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03125 |
| CAS | |
| Molecular Weight | 552.57 |
| Molecular Formula | C30H32O10 |
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Description
Thielavin P is a glucose-6-phosphatase (G6Pase) inhibitor produced by Chaetomium carinthiacum.
Specification
| IUPAC Name | 4-[4-(2,4-dihydroxy-3,5,6-trimethylbenzoyl)oxy-2-hydroxy-3,5,6-trimethylbenzoyl]oxy-2-hydroxy-3,5,6-trimethylbenzoic acid |
| Canonical SMILES | CC1=C(C(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2C)C)C(=O)OC3=C(C(=C(C(=C3C)C)C(=O)O)O)C)O)C)O)C)O)C |
| InChI | InChI=1S/C30H32O10/c1-10-13(4)22(31)16(7)23(32)20(10)29(37)40-27-15(6)12(3)21(25(34)18(27)9)30(38)39-26-14(5)11(2)19(28(35)36)24(33)17(26)8/h31-34H,1-9H3,(H,35,36) |
| InChI Key | GKMFYIPFHCBFIB-UHFFFAOYSA-N |
Properties
| Boiling Point | 849.0±65.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Thielavins as glucose-6-phosphatase (G6Pase) inhibitors: producing strain, fermentation, isolation, structural elucidation and biological activities
Shinichi Sakemi, Hideo Hirai, Toshio Ichiba, Taisuke Inagaki, Yoshinao Kato, Nakao Kojima, Hiroyuki Nishida, Janice C Parker, Toshiyuki Saito, Hiroko Tonai-Kachi, Maria A VanVolkenburg, Nobuji Yoshikawa, Yasuhiro Kojima J Antibiot (Tokyo). 2002 Nov;55(11):941-51. doi: 10.7164/antibiotics.55.941.
High-throughput screening of microbial extracts using rat hepatic microsomal glucose-6-phosphatase (G6Pase) led us to find thielavin B as a G6Pase inhibitor with inhibition of glucose output from glucagon-stimulated hepatocytes. Further searching for more potent analogs identified 11 new thielavins F-P in addition to the known thielavins A and B from a fungus Chaetomium carinthiacum ATCC 46463. Thielavin G showed the strongest activity as a G6Pase inhibitor (IC50=0.33 microM), while the IC50 of thielavin B was 5.5 microM. According to the structure-activity relationship, including authentic thielavins C, D and 3 partial hydrolysates from thielavins A and B, 3 benzoic acid-units and carboxylic acid functions are essential for G6Pase inhibition.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
