Manumycin F

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Manumycin F
Category Antibiotics
Catalog number BBF-02296
CAS 156317-47-4
Molecular Weight 546.62
Molecular Formula C31H34N2O7

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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; asukamycin A1; 2,4,6-Heptatrienamide, 7-cyclohexyl-N-[5-hydroxy-5-[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]-
IUPAC Name (2E,4E,6E)-7-cyclohexyl-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]hepta-2,4,6-trienamide
Canonical SMILES C1CCC(CC1)C=CC=CC=CC(=O)NC2=CC(C3C(C2=O)O3)(C=CC=CC=CC(=O)NC4=C(CCC4=O)O)O
InChI InChI=1S/C31H34N2O7/c34-23-17-18-24(35)27(23)33-26(37)16-10-3-4-11-19-31(39)20-22(28(38)29-30(31)40-29)32-25(36)15-9-2-1-6-12-21-13-7-5-8-14-21/h1-4,6,9-12,15-16,19-21,29-30,34,39H,5,7-8,13-14,17-18H2,(H,32,36)(H,33,37)/b2-1+,4-3+,12-6+,15-9+,16-10+,19-11+/t29-,30-,31+/m1/s1
InChI Key SSHVAUUEPNULMP-JHWDTTIQSA-N

Properties

Appearance Yellow Amorphous Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor)
Boiling Point 910.0°C at 760 mmHg
Melting Point >250°C (dec.)
Density 1.32 g/cm3
Solubility Soluble in Acetonitrile, DMSO

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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