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(E)-13-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-12-methyl-10-oxo-tridec-11-enoic acid

HCID 6476007
NotesReactions
Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
12650-69-0
Standard SMILES
C/C(=C\C(=O)CCCCCCCCC(=O)O)C[C@@H]1OC[C@H](C[C@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O
InChIKey
HRXJGZJQHHUGOH-YINQFVIBSA-N
Molecular formula
C26H44O8
Average molar mass
484.6 g/mol
Monoisotopic mass
484.30361836

Names & identifiers

Preferred name
(E)-13-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-12-methyl-10-oxo-tridec-11-enoic acid
IUPAC
(E)-13-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2R,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-12-methyl-10-oxotridec-11-enoic acid
English name
Mupirocin
Molecular formula
C26H44O9
Molecular weight
500.62

Names & synonyms

(E)-13-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2R,3S)-3-[(1S,2S)-2-hydroxy-1-methyl-propyl]oxiran-2-yl]methyl]tetrahydropyran-2-yl]-12-methyl-10-oxo-tridec-11-enoic acid(E)-13-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-12-methyl-10-oxo-tridec-11-enoic acidMUPIROCIN CALCIUM231-791-2PSEUDOMONIC ACIDPSEUDOMONIC ACID AbactrobanL-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-(2S,3S)-3-(1S,2S)-2-hydroxy-1-methylpropyloxiranylmethyl-3-methyl-, 8-carboxyoctyl ester, (2E)-TurixiTurixinMupricinMUPIROCIN

Database identifiers

CAS
12650-69-0
PubChem CID
6476007

Properties

Computed structural properties

XLogP
3
Topological polar surface area
137 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
8
Rotatable bonds
16
Heavy atoms
34
Formal charge
0
Complexity
678

Physicochemical properties

Melting point
77 · 77-780C
Boiling point
672 ℃ · 672℃
alpha
20 · D20 -19.3° (c = 1 in methanol)
Density
1.183 · 1.183±0.06 g/cm3(Predicted)
Flash point
110 ° · >110°(230°F)
storage temp.
-20 °C · Inert atmosphere,Store in freezer, under -20°C
solubility
2 O: · H2O: 12 mg/mL, soluble
form
solid
pka
4.78 · 4.78±0.10(Predicted)
color
white to tan
optical activity
-15.7 to · [α]/D -15.7 to -20°, c = 1 in methanol
Water Solubility
Soluble in DMSO or methanol. Sparingly soluble in water
λmax
222 nm · 222nm(EtOH)(lit.)
Merck
14 · 14,6302
Stability
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.

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
2
rtecs
RA6907000
hs_code
2941906000
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H317
Precautionary statements
P261-P280

Chemistry & industry

Applications · 8 items

UsesTopical antibiotics. This product is generally used for the inflammation of the skin, eczema, etc., or made into mupirocin ointment in the market.By reversibly binding to isoleucine transfer RNA synthetase, this product can prevent isoleucine incorporated so that the synthesis of all proteins in cells containing isoleucine can be stopped. Mupirocin has a unique mode of action. The epoxide-containing monic acid tail of the molecule is an analog of isoleucine and, as such, is a competitive inhibitor of isoleucyltRNA synthetase in bacterial cells. The corresponding mammalian enzyme is unaffected.

DescriptionMupirocin (pseudomonic acid A) is an antibiotic produced by Pseudomonas fluorescens. It is useful in the treatment of dermal infections, especially those involving S. aureus and S. epidermidis.

Usesantibacterial, antimycoplasmal, isoleucyl-tRNA synthetase inhibitor

UsesMupirocin, is a major component of the pseudomonic acid, an antibiotic complex produced by Pseudomonas fluorescens NCIB 10586. Topical antibacterial.

UsesPseudomonic acid is a potent antibiotic produced by Pseudomonas fluorescens, reported by Fuller et al. in 1971. Pseudomonic acid has broad spectrum activity against Gram positive bacteria and was approved for topical human use in 1985. Pseudomonic acid acts as a potent and selective inhibitor of isoleucyl-tRNA synthetase.

UsesAn antibiotic inhibitor of isoleucyl-tRNA synthetase

Usesvasodilator

General DescriptionMupirocin (pseudomonic acid A, Bactroban) is the majorcomponent of a family of structurally related antibiotics,pseudomonic acids A to D, produced by the submergedfermentation of Pseudomonas fluorescens. Although theantimicrobial properties of P. fluorescens were recordedas early as 1887, it was not until 1971 that Fuller et al.identified the metabolites responsible for this activity. Thestructure of the major and most potent metabolite,pseudomonic acid A (which represents 90%–95% of the activefraction from P. fluorescens), was later confirmed bychemical synthesis to be the 9-hydroxynonanoic acidester of monic acid.The use of mupirocin is confined to external applications.280 Systemic administration of the antibiotic resultsin rapid hydrolysis by esterases to monic acid, which is inactivein vivo because of its inability to penetrate bacteria.Mupirocin has been used for the topical treatment ofimpetigo, eczema, and folliculitis secondarily infected bysusceptible bacteria, especially staphylococci and -hemolyticstreptococci. The spectrum of antibacterial activityof mupirocin is confined to Gram-positive and Gramnegativecocci, including staphylococci, streptococci,Neisseria spp., and M. catarrhalis. The activity of the antibioticagainst most Gram-negative and Gram-positivebacilli is generally poor, with the exception of H. influenzae.It is not effective against enterococci or anaerobicbacteria.Mupirocin interferes with RNA synthesis and protein synthesisin susceptible bacteria. It specifically and reversiblybinds with bacterial isoleucyl tRNA synthase to preventthe incorporation of isoleucine into bacterial proteins.282High-level, plasmid-mediated mupirocin resistance in S. aureushas been attributed to the elaboration of a modifiedisoleucyl tRNA that does not bind mupirocin.283 Inherent resistancein bacilli is likely because of poor cellular penetrationof the antibiotic.

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Major Application
pharmaceutical
InChIKey
MINDHVHHQZYEEK-HBBNESRFSA-N
SMILES
[H][C@@]1(CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O)C[C@@H]2O[C@@]2([H])[C@@H](C)[C@H](C)O
CAS DataBase Reference
12650 · 12650-69-0(CAS DataBase Reference)
FDA UNII
0 GX863OA5 · D0GX863OA5
ATC code
6 AX09,R01AX06 · D06AX09,R01AX06
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
317 · H317
Precautionary statements
261 · P261-P280
WGK Germany
2 · 2
RTECS
6907000 · RA6907000
HS Code
2941906000 · 2941906000
Storage Class
11 · 11 - Combustible Solids

Upstream & downstream products

Upstream raw materials

Zinc silicate

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]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
天津茂田科技有限公司19102267946 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Syntechem Co.,Ltd[email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
广州市亿邦医药科技有限公司+86 (20) 28996708,29078958,28139708,29076128,28133708,28139728,28139738,28133718,021-31663278,021-31663578,021-60538387
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
Beckmann-Kenko GmbH+49 4241 9308 88 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
济南健丰化工有限公司0531-88110457; 18954159893 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
山东铭枫医药科技有限公司053155551677 15315114555 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
南京爱莉生物科技有限公司025-83208295 18913388297 · [email protected]
杭州中美华东制药江东有限公司0571-82907203 15606520558 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
上海遐瑞医药科技有限公司+86 21 61551611
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
上海昶衍化工科技有限公司021-20242659 18930833303 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海湄水化工科技有限公司021-60549325 18616193163
HBCChem, Inc.+1-510-219-6317 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
合肥宏美双圣医药科技有限公司0551-65523315 17705606359 · [email protected]
山东君泰药业有限公司15901008306 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
广州市慈铭生物科技有限公司020-38082199,29065168,38082986,29878298,29866629,4000192398
上海孚一生物科技有限公司+86 (21) 61124340
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]
Additional notes · 1 item

DefinitionChEBI: An alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2 -pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydro ybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.