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Oligomycin A

Oligomycin A structure

CAS No:
579-13-5
Formula:
C45H74O11
Chemical Name:
Oligomycin A
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′,6,8,10,12,14,16,28,29-nonamethyl-,(1R,2′R,4E,5′S,6S,6′S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,28S,29R)-;Oligomycin A;Spiro[2,26-dioxabicyclo[23.3.1]nonacosane-27,2′-[2H]pyran],oligomycin A deriv.;(1R,2′R,4E,5′S,6S,6′S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,28S,29R)-22-Ethyl-3′,4′,5′,6′-tetrahydro-7,11,14,15-tetrahydroxy-6′-[(2R)-2-hydroxypropyl]-5′,6,8,10,12,14,16,28,29-nonamethylspiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2′-[2H]pyran]-3,9,13-trione;MCH 32;11030-76-5;21307-25-5;31422-20-5;1255037-37-6
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Oligomycin A, created by Streptomyces, acts as a mitochondrial F0F1-ATPase inhibitor, with a Ki of 1 μM; Oligomycin A shows anti-fungal activity.

A closely related group of toxic substances elaborated by various strains of Streptomyces. They are 26-membered macrolides with lactone moieties and double bonds and inhibit various ATPases, causing uncoupling of phosphorylation from mitochondrial respiration. Used as tools in cytochemistry. Some specific oligomycins are RUTAMYCIN, peliomycin, and botrycidin (formerly venturicidin X).

Oligomycin A Basic Attributes

Molecular Weight：

791.06

Exact Mass：

791.06

EC Number：

215-767-9

DSSTox ID：

DTXSID7040570

HScode：

29419090

Characteristics

PSA：

180

Appearance：

white to off-white

Density：

1.116 g/cm³

Melting Point：

140-141 °C

Boiling Point：

886.3°C at 760 mmHg

Flash Point：

252.0±27.8 °C

Refractive Index：

1.543

Water Solubility：

Soluble in DMSO, ethanol or acetone

Storage Conditions：

−20°C

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

2811

wgk germany：

hazard class code：

22-68/20/21/22-20/21/22

safety instructions：

36/37-24/25

RTECS Number：

RK3325000

Marks：

Xn,T

Hazard Statements：

H302

GHS Classification：

|Danger|H301 (50%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P301+P310, P301+P312, P307+P311, P321, P330, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 128 companies from 1 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial 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.)

MeSH Entry Terms：

Oligomycin

Oligomycin A Use and Manufacturing

Oligomycin A is the dominant analogue of a class of macrocyclic lactones isolated from selected strains of Streptomyces sp.. Oligomycin A is an inhibitor of mitochondrial F1F0-ATPase. It induces apoptosis in a variety of cell types, makes cells more susceptible to cell death, and also leads to a switch in the death mode from apoptosis to necrosis. Oligomycin A exhibits a broad biological profile including antifungal, antitumor and nematocidal activities.

Computed Properties

Molecular Weight:791.1
XLogP3:7.1
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:3
Exact Mass:790.52311317
Monoisotopic Mass:790.52311317
Topological Polar Surface Area:180
Heavy Atom Count:56
Complexity:1390
Undefined Atom Stereocenter Count:18
Undefined Bond Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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