MC-033
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| Category | Antibiotics |
| Catalog number | BBF-03644 |
| CAS | 134615-15-9 |
| Molecular Weight | 941.45 |
| Molecular Formula | C49H61ClO16 |
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Description
MC-033, an inhibitor of cholesterol biosynthesis, is produced by the strain of Streptomyces sp. A3761. It inhibited the synthesis of cholesterol from Mevalonic acid with IC50 of 1.06×10-5 mol/L. It also showed weak anti-gram-positive bacteria activity and inhibited the growth of HL-60 cells.
Specification
| Synonyms | MC 033; Chlorothricin, 3B-O-de(3-chloro-6-methoxy-2-methylbenzoyl)-, 4B-(3-chloro-6-methoxy-2-methylbenzoate) |
| IUPAC Name | (3R,6R,7Z,13R,16S,17S,21R,22R)-17-[(2S,4R,5S,6R)-5-[(2R,4R,5S,6R)-5-(3-chloro-6-hydroxy-2-methylbenzoyl)oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-28-hydroxy-3,22-dimethyl-23,26-dioxo-24,27-dioxapentacyclo[23.2.1.01,6.013,22.016,21]octacosa-4,7,14,25(28)-tetraene-4-carboxylic acid |
| Canonical SMILES | CC1CC23C(C=CCCCCC4C=CC5C(C4(C(=O)OC(=C2O)C(=O)O3)C)CCCC5OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)OC(=O)C8=C(C=CC(=C8C)Cl)O)O)O)C=C1C(=O)O |
| InChI | InChI=1S/C49H61ClO16/c1-23-22-49-28(19-30(23)44(55)56)12-9-7-6-8-11-27-15-16-29-31(48(27,5)47(59)65-42(43(49)54)46(58)66-49)13-10-14-36(29)62-37-20-34(52)40(25(3)60-37)63-38-21-35(53)41(26(4)61-38)64-45(57)39-24(2)32(50)17-18-33(39)51/h9,12,15-19,23,25-29,31,34-38,40-41,51-54H,6-8,10-11,13-14,20-22H2,1-5H3,(H,55,56)/b12-9-/t23-,25-,26-,27-,28-,29+,31-,34-,35-,36+,37-,38-,40-,41-,48-,49?/m1/s1 |
| InChI Key | ZELGFPMKYWIDEX-XRIHGTRMSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Boiling Point | 1016.081°C at 760 mmHg |
| Melting Point | 285-287°C |
| Density | 1.426 g/cm3 |
Reference Reading
1. New cholesterol biosynthesis inhibitors MC-031 (O-demethylchlorothricin), -032 (O-demethylhydroxychlorothricin), -033 and -034
A Kawashima, Y Nakamura, Y Ohta, T Akama, M Yamagishi, K Hanada J Antibiot (Tokyo). 1992 Feb;45(2):207-12. doi: 10.7164/antibiotics.45.207.
In the course of our screening for microbial compounds which possessed inhibitory activities against biosynthesis of cholesterol from mevalonate, we isolated four new compounds from the cultural broth of Streptomyces sp. A7361. They are structurally related to, but distinct from chlorothricin.
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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 ╳
