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Mupirocin

CAT: 0926-AM26100-02Size: 10 gDry Ice: NoHazardous: No
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CAT#:0926-AM26100-02Size:10 g
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
12650-69-0
Synonyms
(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 a cid 8-carboxyoctyl ester; BRL 4910A, Pseudomonic acid; Bactoderm
Smiles
C[C@H] ([C@H]1[C@@H] (O1) C[C@H]2CO[C@H] ([C@@H] ([C@@H]2O) O) C/C (=C/C (=O) OCCCCCCCCC (=O) O) /C) [C@H] (C) O
Molecular Formula
C26H44O9
Molecular Weight
500.62 g/mol
Controlled
No

Chemical Information

Mupirocin

Mupirocin is 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-2H-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-hydroxybutan-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. It has a role as an antibacterial drug, a protein synthesis inhibitor and a bacterial metabolite. It is a monocarboxylic acid, a triol, an epoxide, a secondary alcohol, a member of oxanes and an alpha,beta-unsaturated carboxylic ester. It is a conjugate acid of a mupirocin(1-).

CAS Number12650-69-0
PubChem CID446596
IUPAC Name9-[(E)-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]oxynonanoic acid
Molecular FormulaC26H44O9
Molecular Weight500.6
XLogP3
Topological Polar Surface Area146
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count17
Heavy Atom Count35
Formal Charge0
Complexity694
SMILES
C[C@H]([C@H]1[C@@H](O1)C[C@H]2CO[C@H]([C@@H]([C@@H]2O)O)C/C(=C/C(=O)OCCCCCCCCC(=O)O)/C)[C@H](C)O
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
Chemical Structure
2D Structure
2D structure of Mupirocin
CAS: 12650-69-0
CID: 446596
Formula: C26H44O9
MW: 500.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight500.6
XLogP33
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count17
Exact Mass500.29853298
Monoisotopic Mass500.29853298
Topological Polar Surface Area146 Ų
Heavy Atom Count35
Formal Charge0
Complexity694
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
B4872-5.1Mupirocin

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