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Rutamycin

Rutamycin structure

CAS No:
1404-59-7
Formula:
C44H72O11
Chemical Name:
Rutamycin
Synonyms:
Spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2′-[2H]pyran]-3,9,13-trione,22-ethyl-3′,4′,5′,6′-tetrahydro-7,11,14,15-tetrahydroxy-6′-[(2R)-2-hydroxypropyl]-5′,6,8,10,12,14,16,29-octamethyl-,(1S,2′R,4E,5′S,6S,6′S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,29R)-;Rutamycin;Oligomycin A,26-demethyl-;Spiro[2,26-dioxabicyclo[23.3.1]nonacosane-27,2′-[2H]pyran],oligomycin A deriv.;(1S,2′R,4E,5′S,6S,6′S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,29R)-22-Ethyl-3′,4′,5′,6′-tetrahydro-7,11,14,15-tetrahydroxy-6′-[(2R)-2-hydroxypropyl]-5′,6,8,10,12,14,16,29-octamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2′-[2H]pyran]-3,9,13-trione;A 272;RR 32705;Oligomycin D;Rutamycin A;1255037-35-4
Categories:
Organic Chemistry > Lactones

Description

A macrolide antibiotic of the oligomycin group, obtained from Streptomyces rutgersensis. It is used in cytochemistry as a tool to inhibit various ATPases and to uncouple oxidative phosphorylation from electron transport and also clinically as an antifungal agent.

Rutamycin Basic Attributes

Molecular Weight：

777.042

Exact Mass：

777.04

Characteristics

PSA：

180.05000

XLogP3：

5.63660

Density：

1.15g/cm3

Melting Point：

116-119 °C

Boiling Point：

883.4ºC at 760 mmHg

Flash Point：

253ºC

Refractive Index：

1.544

Toxicity：

LD50 oral in mouse: 800mg/kg

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

2811

Drug Information

MeSH：

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|Chemical agents that uncouple oxidation from phosphorylation in the metabolic cycle so that ATP synthesis does not occur. Included here are those IONOPHORES that disrupt electron transfer by short-circuiting the proton gradient across mitochondrial membranes. (See all compounds classified as Uncoupling Agents.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

MeSH Entry Terms：

A 272

Rutamycin Use and Manufacturing

Oligomycin D (rutamycin) is macrocyclic lactone belonging to the oligomycin class but identified from different species of Streptomyces in 1961. Like oligomycin A, oligomycin D inhibits mitochondrial F1F0-ATPase and is an important bioprobe to study the organisation of ATPase on the mitochondrial membrane. Oligomycin D exhibits a broad biological profile including antifungal, antitumor and nematocidal activities.

Computed Properties

Molecular Weight:777.0
XLogP3:6.6
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:3
Exact Mass:776.50746311
Monoisotopic Mass:776.50746311
Topological Polar Surface Area:180
Heavy Atom Count:55
Complexity:1360
Defined Atom Stereocenter Count:17
Defined Bond Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes