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MC-034

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Category Antibiotics
Catalog number BBF-03645
CAS 134615-16-0
Molecular Weight 957.45
Molecular Formula C49H61ClO17

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

MC-034, 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 18.3×10-5 mol/L. It also showed weak anti-gram-positive bacteria activity and inhibited the growth of HL-60 cells.

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Synonyms MC 034; Chlorothricin, 3B-O-de(3-chloro-6-methoxy-2-methylbenzoyl)-2A-hydroxy-, 4B-(3-chloro-6-methoxy-2-methylbenzoate)
IUPAC Name (3R,6R,7Z,13R,16S,17S,21R,22R)-17-[(2R,4R,5S,6R)-5-[(2S,4R,5S,6R)-5-(3-chloro-6-hydroxy-2-methylbenzoyl)oxy-4-hydroxy-6-methyloxan-2-yl]oxy-3,4-dihydroxy-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)CCCC5OC6C(C(C(C(O6)C)OC7CC(C(C(O7)C)OC(=O)C8=C(C=CC(=C8C)Cl)O)O)O)O)C=C1C(=O)O
InChI InChI=1S/C49H61ClO17/c1-22-21-49-27(19-29(22)43(56)57)12-9-7-6-8-11-26-15-16-28-30(48(26,5)47(60)66-41(42(49)55)45(59)67-49)13-10-14-34(28)63-46-38(54)37(53)40(25(4)62-46)64-35-20-33(52)39(24(3)61-35)65-44(58)36-23(2)31(50)17-18-32(36)51/h9,12,15-19,22,24-28,30,33-35,37-40,46,51-55H,6-8,10-11,13-14,20-21H2,1-5H3,(H,56,57)/b12-9-/t22-,24-,25-,26-,27-,28+,30-,33-,34+,35+,37-,38?,39-,40-,46+,48-,49?/m1/s1
InChI Key GDKOCPOPNXYMKU-ITKXNXJMSA-N
Antibiotic Activity Spectrum Gram-positive bacteria; neoplastics (Tumor)
Boiling Point 1032.4°C at 760 mmHg
Melting Point 267-269°C
Density 1.45 g/cm3
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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