Home > Compound List > Compound details
12650-69-0 molecular structure
click picture or here to close

9-({4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl}oxy)nonanoic acid

ChemBase ID: 293
Molecular Formular: C26H44O9
Molecular Mass: 500.62216
Monoisotopic Mass: 500.29853299
SMILES and InChIs

SMILES:
[C@H]1([C@H](CO[C@H]([C@@H]1O)C/C(=C/C(=O)OCCCCCCCCC(=O)O)/C)C[C@H]1[C@H]([C@H]([C@H](C)O)C)O1)O
Canonical SMILES:
OC(=O)CCCCCCCCOC(=O)/C=C(/C[C@@H]1OC[C@@H]([C@H]([C@H]1O)O)C[C@@H]1O[C@H]1[C@H]([C@@H](O)C)C)\C
InChI:
InChI=1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1
InChIKey:
MINDHVHHQZYEEK-HBBNESRFSA-N

Cite this record

CBID:293 http://www.chembase.cn/molecule-293.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
9-({4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl}oxy)nonanoic acid
9-{[(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}nonanoic acid
IUPAC Traditional name
mupirocin
9-({4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl}oxy)nonanoic acid
Brand Name
Bactoderm
Bactroban
Bactroban Nasal
Centany
Turixin
Synonyms
mupirocin
Mupirocin
Bifido Selective Supplement A
MUP Supplement
Mupirocin solution
Mupirocin Supplement
5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-3-methyl-[2E,8[2S,3S(1S,2S)]]-L-talonon-2-enonic acid 8-carboxyoctyl ester
BRL 4910A
Mupirocin
(2E)-5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]-oxiranyl]methyl]-3-methyl-L-talo-non-2-enonic Acid 8-Carboxyoctyl Ester
Bactoderm
Bactroban
Bactroban Ointment
Mupirocin Neo-Sensitabs
Mupricin
Pseudomonic Acid A
Turixin
trans-Pseudomonic Acid
MRC
Pseudomonic acid
Mupirocine
Bifido 选择性添加剂 A
MUP 添加剂
莫匹罗星 溶液
莫匹罗星添加剂
CAS Number
12650-69-0
EC Number
231-791-2
MDL Number
MFCD01711620
PubChem SID
46505594
24724542
160963756
PubChem CID
446596
ATC CODE
D06AX09
R01AX06
CHEMBL
719
Chemspider ID
393914
DrugBank ID
DB00410
KEGG ID
D01076
Unique Ingredient Identifier
D0GX863OA5
Wikipedia Title
Mupirocin
Medline Plus
a688004

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.8340716  H Acceptors
H Donor LogD (pH = 5.5) 1.7011259 
LogD (pH = 7.4) -0.07094509  Log P 2.4513257 
Molar Refractivity 129.3941 cm3 Polarizability 51.53534 Å3
Polar Surface Area 146.05 Å2 Rotatable Bonds 17 
Lipinski's Rule of Five false 
Log P 2.25  LOG S -4.28 
Solubility (Water) 2.65e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
DMSO: ≥10 mg/mL expand Show data source
Ethanol expand Show data source
Methanol expand Show data source
Apperance
White Crystalline Solid expand Show data source
white to tan powder expand Show data source
Melting Point
77-78°C expand Show data source
Optical Rotation
[α]/D -15.7 to -20°, c = 1 in methanol expand Show data source
Storage Condition
-20°C Freezer, Under Inert Atmosphere expand Show data source
RTECS
RA6907000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
room temp expand Show data source
Admin Routes
topical expand Show data source
Half Life
20 to 40 minutes expand Show data source
Protein Bound
97% expand Show data source
Legal Status
Rx Only (US) expand Show data source
Pregnancy Category
B (US) expand Show data source
US Licence
Bactroban expand Show data source
Purity
≥92% (HPLC) expand Show data source
Grade
for microbiology expand Show data source
Certificate of Analysis
Download expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Empirical Formula (Hill Notation)
C26H44O9 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00410 external link
Item Information
Drug Groups approved; investigational
Description Mupirocin (pseudomonic acid A, or Bactroban or Centany) is an antibiotic originally isolated from Pseudomonas fluorescens. It is used topically, and is primarily effective against Gram-positive bacteria. Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations.
Mupirocin has a unique mechanism of action, which is selective binding to bacterial isoleucyl-tRNA synthetase, which halts the incorporation of isoleucine into bacterial proteins. Because this mechanism of action is not shared with any other antibiotic, mupirocin has few problems of antibiotic cross-resistance.
Indication For the treatment of Staphylococci nasal carriers.
Pharmacology Mupirocin, an antibiotic produced from Pseudomonas fluorescens, is structurally unrelated to any other topical or systemic antibiotics. Mupirocin is used to treat infection caused by Staphylococcus aureus and beta-hemolytic streptococci including Streptococcus pyogenes. This antibiotic has little, if any, potential for cross-resistance with other antibiotics.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic. Following intravenous or oral administration, mupirocin is rapidly metabolized. The principal metabolite is monic acid, which has no antibacterial activity.
Absorption No measurable systemic absorption
Half Life 20 to 40 minutes
Protein Binding 97%
Elimination Following the application of Centany (mupirocin ointment),2% to a 400 cm2 area on the back of 23 healthy volunteers once daily for 7 days, the mean (range) cumulative urinary excretion of monic acid over 24 hrs following the last administration was 1.25% (0.2% to 3.0%) of the administered dose of mupirocin.
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - M7694 external link
Biochem/physiol Actions
Antibiotic; inhibits isoleucyl-tRNA synthetase (IRS).
Sigma Aldrich - 89914 external link
Components
(per vial, sufficient for 500 ml medium)Mupirocin 25 mgSterile Distilled Water 5 ml
Application
A selective supplement for the selective isolation of Bifidobacterium species by colony count technique from milk products.
Toronto Research Chemicals - M794000 external link
Mupirocin, is a major component of the pseudomonic acid, an antibiotic complex produced by Pseudomonas fluorescens NCIB 10586. Topical antibacterial.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Hughes, J., et al.: J. Antibiot., 31, 330 (1978)
  • • Ward, A., et al.: Drugs, 32, 425 (1978)
  • • Casewell, M.W., et al.: J. Antimicrob. Chemother., 19, 1 (1978)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle