Manumycin E

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Manumycin E
Category Antibiotics
Catalog number BBF-02295
CAS 156250-43-0
Molecular Weight 534.61
Molecular Formula C30H34N2O7

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Description

It is produced by the strain of Str. sp. WB-83. It has anti-gram-positive bacteria and Escherichia coli effects, but the effect is very weak against other anti-gram-negative bacteria, and has no effect on fungi. It inhibits RAS Faraday base transfer with IC50 of 5 μmol/L. It has weak cytotoxic activity against human cloned cancer cell lines HCT-116 (IC50 is 15.6 μg/mL).

Specification

Synonyms Asukamycin E; 2,4,6-Undecatrienamide, N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxo-1,3,5-heptatrienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-10-methyl-, (2E,4E,6E)-
IUPAC Name (2E,4E,6E)-N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-7-oxohepta-1,3,5-trienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-10-methylundeca-2,4,6-trienamide
Canonical SMILES CC(C)CCC=CC=CC=CC(=O)NC1=CC(C2C(C1=O)O2)(C=CC=CC=CC(=O)NC3=C(CCC3=O)O)O
InChI InChI=1S/C30H34N2O7/c1-20(2)13-9-5-3-4-6-10-14-24(35)31-21-19-30(38,29-28(39-29)27(21)37)18-12-8-7-11-15-25(36)32-26-22(33)16-17-23(26)34/h3-8,10-12,14-15,18-20,28-29,33,38H,9,13,16-17H2,1-2H3,(H,31,35)(H,32,36)/b5-3+,6-4+,8-7+,14-10+,15-11+,18-12+/t28-,29-,30+/m1/s1
InChI Key VVOBNOKKAUOIJN-YBEHSRRHSA-N

Properties

Appearance Yellow Amorphous Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor)
Boiling Point 878.8±65.0°C (Predicted)
Melting Point >250°C (dec.)
Density 1.29±0.1 g/cm3 (Predicted)
Solubility Soluble in Acetonitrile, Methanol

Reference Reading

1. Manumycins E, F and G, new members of manumycin class antibiotics, from Streptomyces sp
Y Z Shu, S Huang, R R Wang, K S Lam, S E Klohr, K J Volk, D M Pirnik, J S Wells, P B Fernandes, P S Patel J Antibiot (Tokyo). 1994 Mar;47(3):324-33. doi: 10.7164/antibiotics.47.324.
Three new manumycin class antibiotics, namely manumycins E, F and G, were isolated from the culture broth of Streptomyces sp. strain WB-8376. Their structures were established by spectroscopic methods, and the S configuration of C-4 in the epoxycyclohexenone moiety was determined by CD exciton chirality method for each of the three compounds. Manumycins E, F and G are active against Gram-positive bacteria, and have moderate inhibitory effects on the farnesylation of p21 ras protein. They demonstrated weak cytotoxic activity against human colon tumor cell HCT-116.

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