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4-(2-(2-Ethyl-5'-(6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl)-3'-methyl(2,2'-bioxolan)-5-yl)-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro(4.5)decan-7-yl)-3-methoxy-2-methylpentanoic acid

HCID 4243
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
22373-78-0
Standard SMILES
CCC1(C2OC(C3OC(O)(CO)C(C)CC3C)CC2C)CCC(C2(C)CCC3(CC(O)C(C)C(C(C)C(OC)C(C)C(=O)O)O3)O2)O1
InChIKey
GAOZTHIDHYLHMS-UHFFFAOYSA-N
Molecular formula
C36H62O11
Average molar mass
670.9 g/mol
Monoisotopic mass
670.42921279

Overview

monensin has been reported in Streptomyces cinnamonensis with data available.

Names & identifiers

Preferred name
4-(2-(2-Ethyl-5'-(6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl)-3'-methyl(2,2'-bioxolan)-5-yl)-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro(4.5)decan-7-yl)-3-methoxy-2-methylpentanoic acid
IUPAC
4-[2-[5-ethyl-5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]oxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-3-methoxy-2-methylpentanoic acid
English name
Monensin sodium salt
Molecular formula
C36H63NaO12
Molecular weight
710.87

Names & synonyms

DTXSID108601974-(2-(2-Ethyl-5'-(6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl)-3'-methyl(2,2'-bioxolan)-5-yl)-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro(4.5)decan-7-yl)-3-methoxy-2-methylpentanoic acid4-(2-{2-Ethyl-5'-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3'-methyl[2,2'-bioxolan]-5-yl}-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl)-3-methoxy-2-methylpentanoic acidRefChem:1069773DTXCID60197066Coban (Salt/Mix)Romensin (Salt/Mix)Rumensin (Salt/Mix)MLS006011801SCHEMBL1143131CHEMBL4788880GAOZTHIDHYLHMS-UHFFFAOYSA-N
Show more names
CobanRUMENSINCoban45SodiummonensinMonomycin sodiumMonensinsodiumsalMONENSINSODIUM,USPMonensin sodium 40%Monensin sodium saltPreviouscas:22136-43-2
AKOS0158428891,6-Dioxaspiro[4.5]decane-7-butyric acid, 2-[5-ethyltetrahydro-5-[tetrahydro-3-methyl-5-[tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl]-2-furyl]-2-furyl]-9-hydroxy-.beta.-methoxy-.alpha.,.gamma.,2,8-tetramethyl-SMR0047034861, 2-[5-ethyltetrahydro-5-[tetrahydro-3-methyl-5-[tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl]-2-furyl]-2-furyl]-9-hydroxy-.beta.-methoxy-.alpha.,.gamma.,2,8-tetramethyl-, monosodium salt1,6-Dioxaspiro[4.5]decane-7-butanoic acid, 2-[2-ethyloctahydro-3'-methyl-5'-[tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl][2,2'-bifuran]-5-yl]-9-hydroxy-.beta.-methoxy-.alpha.,.gamma.,2,8-tetramethyl-2-[2-Ethyloctahydro-3'-methyl-5'-[tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl][2,2'-bifuran-5-yl]]-9-hydroxy-.beta.-methoxy-.alpha.,.gamma.,2,8-tetramethyl-1,6-dioxapsiro[4.5]decan-7-butanoic acidStereoisomer of 2-[2-ethyloctahydro-3'-methyl-5'-[tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl][2,2'-bifuran-5-yl]]-9-hydroxy-.beta.-methoxy-.alpha.,.gamma.,2,8-tetramethyl-1,6-dioxaspiro[4.5]decan-7-butanoic acid

Properties

Computed structural properties

XLogP
4.2
Topological polar surface area
153 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
11
Rotatable bonds
10
Heavy atoms
47
Formal charge
0
Complexity
1,110

Physicochemical properties

Melting point
267 · 267-269 C
alpha
57.3 · 57.3 º (c=4.0, in MeOH)
storage temp.
2 · 2-8°C
solubility
50 mg/ml · Soluble in methanol at 50mg/ml
form
Off-white to beige solid
color
White
BRN
4122200 · 4122200
Stability
2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
InChIKey
XOIQMTLWECTKJL-BEMBKCOJSA-M
LogP
3.716 · 3.716 (est)
FDA UNII
1 GS872GAFV · 1GS872GAFV
EPA Substance Registry System
Monensin, monosodium salt (22373-78-0)
UNSPSC Code
12352200 · 12352200
Symbol(GHS)
6 · GHS06,GHS08,GHS09
Signal word
Danger

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
3
rtecs
JH2830000
ridadr
UN 3462 6.1/PG 2
hs_code
29419090
risk_code
25-26/27/28
Signal word
Danger
Symbol(GHS)
GHS06,GHS08,GHS09
hazard_code
T,T+
safety_code
36/37/39-45-22
hazard_class
6.1(a)
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
II
target organs
Heart,muscle
Hazard statements
H300-H319-H334-H373-H411
Hazard Classifications
Acute Tox. 2 OralAquatic Chronic 2Eye Irrit. 2STOT RE 2
Precautionary statements
P260-P264-P273-P301+P310-P304+P340+P312-P305+P351+P338

Chemistry & industry

Applications · 6 items

DescriptionMonensin is a naturally occuring ionophorous antibiotic that preferentially forms complexes with monovalent cations to enable transport across lipid membranes. Through its ability to affect pH and the sodium-potassium balance of a cell, monensin can induce cell death in Gram-positive bacteria such as Micrococcus, Bacillus, and Staphylococcus (MICs = 1-12.5 μg/ml), reduce proliferation of P. falciparum and Coccicdium protozoa, and also prevent replication of certain viruses.

UsesPoliether antibiotic. Coccidiostat.

Usesantifungal

Usesantibacterial

UsesMonensin sodium salt is used in potentiometric and spectroscopic studies of alkali metal ion complexes. Monensin (Na) is a polyether small molecule ionophore, capable of forming stable complexes to monovalent cations with specific affinity for Na+. Monensin presents a highly lipophilic scaffold around the bound ion, allowing movement of the complex through the lipid bilayer and consequent transport of the ion out of the cell. Excessive flux of ions out of the cell produces a cytotoxic effect and generates the antibiotic properties of Monensin.

General DescriptionMonensin is a polyether ionophoric antibiotic, which is produced by Streptomyces cinnamonensis. It is used to treat bacterial, fungal and parasitic infections. Monensin prevents the growth of colon cancer cells. It facilitates the transport of sodium and potassium ions between intracellular and extracellular spaces. Monensin prevents coccidiosisin poultry production.

Upstream & downstream products

Downstream products

Monensin

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
22373-78-0
PubChem CID
4243
DTXSID
DTXSID10860197
ChEMBL
CHEMBL4788880
Hazard statements
300 · H300-H319-H334-H373-H411
Precautionary statements
260 · P260-P264-P273-P301+P310-P304+P340+P312-P305+P351+P338
target organs
Heart,muscle
Hazard Codes
T,T+
Risk Statements
25 · 25-26/27/28
Safety Statements
36 · 36/37/39-45-22
RIDADR
3462 · UN 3462 6.1/PG 2
WGK Germany
3 · 3
RTECS
2830000 · JH2830000
HazardClass
6.1 · 6.1(a)
PackingGroup
II
HS Code
29419090 · 29419090
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
2 OralAquatic · Acute Tox. 2 OralAquatic Chronic 2Eye Irrit. 2STOT RE 2
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18062128043 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
Cangzhou Wanyou New Material Technology Co.,Ltd18631714998 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
上海钰康生物科技有限公司+86-18930848214 +86-021-56762820 · [email protected]
医恩医疗系统研发(上海)有限公司021-58958002 18930822973 · [email protected]
南京美博生物科技有限公司025-58619198 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
Xiamen AmoyChem Co., Ltd+86-86-5926051114 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
上海诺宝化工有限公司+86(0)21 60484900
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
上海鑫圭生物科技有限公司15121041756 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
江苏倍达医药科技有限公司0512-63009836 18994340901 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
Alfa Chemistry1-516-6625404 · [email protected]
Hebei Runbin Biotechnology Co. LTD13180553332 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
北京诺其雅盛生物科技有限公司4000-819-385 010-62329685 13718666987
九鼎化学(上海)科技有限公司4009209199 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]