MOCIMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C43H60N2O12
Molecular Weight	796.9427
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	7
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](C(=O)NC\C=C\C=C(/C)[C@@H](OC)C(C)[C@@H]1O[C@H](\C=C\C=C\C=C(/C)C(=O)C2=C(O)C=CNC2=O)[C@H](O)[C@@H]1O)[C@@]3(O)O[C@@H](\C=C\C=C/C)C(C)(C)[C@@H](O)[C@H]3O

InChI

InChIKey=HMSYAPGFKGSXAJ-PAHGNTJYSA-N

InChI=1S/C43H60N2O12/c1-9-11-13-21-31-42(6,7)38(50)39(51)43(54,57-31)28(10-2)40(52)44-23-17-16-19-26(4)36(55-8)27(5)37-35(49)34(48)30(56-37)20-15-12-14-18-25(3)33(47)32-29(46)22-24-45-41(32)53/h9,11-22,24,27-28,30-31,34-39,48-51,54H,10,23H2,1-8H3,(H,44,52)(H2,45,46,53)/b11-9-,14-12+,17-16+,20-15+,21-13+,25-18+,26-19+/t27-,28-,30-,31+,34+,35+,36-,37+,38+,39-,43-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3356609
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/994327

Mocimycin (also known as kyrromycin) was isolated from Streptomyces ramocissimus and tested in vitro against wide range of bacterias. Although having showed good results, drug did not enter clinical trials. Mocimycin acts by binding tightly and specifically to bacterial EF-Tu. Upon administration the antibiotic prevents EF-Tu-GDP from leaving the ribosome and thus inhibits bacterial protein synthesis. Nowadays, the antibiotic is mainly used to study bacterial protein synthesis at the level of elongation factor EF-Tu-GDP release.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial elongation factor Tu 2 Target ID: Bacterial elongation factor Tu Sources: https://www.ncbi.nlm.nih.gov/pubmed/3356609	Inhibitor 8297		10.0 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/994327	Curative		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antibiotic X-5108. V. Structures of antibiotic X-5108 and mocimycin.	1973 Dec 12	4773251
Antibiotic X-5108. VII. Absolute stereochemistry of 8-amino-3-methoxy-2,4-dimethyl-4,6-octadienal, a compound derived from antibiotic X-5108 and mocimycin.	1974 Apr 27	4833349
Antibacterial activity of efrotomycin.	1976 Oct	994327
Antibiotic X-5108. IX. Chemical conversion of mocimycin to aurodox and derivatives of aurodox, goldinamine and mocimycin.	1979 Apr	381270

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Mocimycin was tested against different bacterial strains. MIC values (24h incubation) were: 0.39 ug/ml for Hemophilus influenzae, 150 ug/ml for Shigella sp., 300 ug/ml for Staphyloccus aureus, 0.78 ug/ml for Streptococcus pneumoniae, <0.4 ug/ml for Streptococcus pyogenes.

Name

Type

Language

MOCIMYCIN

Official Name

English

MOCIMYCIN [MART.]

Common Name

English

mocimycin [INN]

Common Name

English

MYC 8003

Code

English

NSC-316094

Code

English

DELVOMYCIN

Common Name

English

MYC-8003

Code

English

MOCIMYCIN [MI]

Common Name

English

KIRROMYCIN

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID201023647