Mupirocin

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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

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 Number	12650-69-0
PubChem CID	446596
IUPAC Name	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
Molecular Formula	C26H44O9
Molecular Weight	500.6
XLogP	3
Topological Polar Surface Area	146
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	17
Heavy Atom Count	35
Formal Charge	0
Complexity	694

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

CAS: 12650-69-0

CID: 446596

Formula: C26H44O9

MW: 500.6

Interactive 3D Structure

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Computed Properties

Property	Value
Molecular Weight	500.6
XLogP3	3
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	17
Exact Mass	500.29853298
Monoisotopic Mass	500.29853298
Topological Polar Surface Area	146 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	694
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
B4872-5.1	Mupirocin

Mupirocin

Chemical Information

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