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Mupirocin

CAT: 0127-OR1029741-04Size: 100 gDry Ice: NoHazardous: No
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CAT#:0127-OR1029741-04Size:100 g
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CAS Number
12650-69-0
Synonyms
9-[ (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
Purity
98%
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

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
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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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