Natural Product (NP) Details

General Information of the NP (ID: NP1351)
Name
Mupirocin
Synonyms
Mupirocin; 12650-69-0; Pseudomonic acid; Bactroban; Mupirocine; Centany; Pseudomonic acid A; Mupirocina; Mupirocinum; BRL 4910A; BRL-4910A; UNII-D0GX863OA5; 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; Bactroban (TN); CHEMBL719; CHEBI:7025; D0GX863OA5; MRC; Bactoderm; 6-Chloro-2,4-dimethoxy pyrimidine; MFCD01711620; NCGC00164554-03; Plasimine; mupirocin calcium salt; 9-(((E)-4-((2S,3R,4R,5S)-3,4-dihydroxy-5-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyl)oxy)nonanoic acid; L-talo-Non-2-enonic acid, 5,9-anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiranyl]methyl]-3-methyl-, 8-carboxyoctyl ester, (2E)-; Mupirocine [French]; Mupirocinum [Latin]; Mupirocina [Spanish]; C26H44O9; Bactroban Ointment; BRL-4910F; 80558-54-9; Centany (TN); trans-Pseudomonic acid; Mupirocin Neo-Sensitabs; Mupirocin (USP/INN); SR-05000001947; 115074-43-6; 73346-79-9; 1jzs; Mupirocin [USAN:USP:INN:BAN]; Mupirocin,(S); 9-((E)-4-((2S,3R,4R,5S)-3,4-dihydroxy-5-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyloxy)nonanoic acid; mupirocin lithium salt; CPD000471888; SCHEMBL3291; DSSTox_CID_26438; DSSTox_RID_81614; DSSTox_GSID_46438; 8-Carboxyoctyl (E)-4-(2S,3R,4R,5S)-5-((2S,3S,4S,5S)-2,3-epoxy-5-hydroxy-4-methylhexyl)-3,4-dihydroxytetrahydro-2H-pyran-2-yl)-3-methylcrotonat; MLS001074711; BIDD:GT0320; Mupirocin, Pseudomonic Acid A; cid_446596; SCHEMBL1027618; Pseudomonic acid A lithium salt; DTXSID0046438; CHEBI:94519; GTPL10916; AOB6353; HMS2234E20; HMS3259L05; HMS3712K03; Pharmakon1600-01505706; HY-B0958; ZINC4102194; Tox21_112183; BDBM50290686; MFCD11977847; NSC759182; NSC815348; AKOS015994756; Mupirocin, >=92% (HPLC), powder; CCG-213522; DB00410; KS-5137; NC00620; NSC 759182; NSC-759182; NSC-815348; NCGC00164554-05; NCGC00164554-06; (E)-(2S,3R,4R,5S)-5-((2S,3S,4S,5S)-2,3-Epoxy-5-hydroxy-4-methylhexyl)tetrahydro-3,4-dihydroxy-beta-methyl-2H-pyran-2-crotonic acid, ester with 9-hydroxynonanoic acid; AS-11580; SMR000471888; SBI-0206892.P001; AB0010371; CAS-12650-69-0; M2955; S4297; C11758; D01076; M-8680; AB01563109_01; Mupirocin, Antibiotic for Culture Media Use Only; Q413578; SR-05000001947-1; SR-05000001947-2; BRD-K15262564-001-06-9; Mupirocin, United States Pharmacopeia (USP) Reference Standard; 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; 9-((E)-4-((2S,3R,4R,5S)-3,4-dihydroxy-5-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)-tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyloxy)nonanoic acid; 9-((E)-4-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-3-methyl-but-2-enoyloxy)-nonanoic acid; 9-((E)-4-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)oxiranylmethyl]tetrahydro-pyran-2-yl}-3-methyl-but-2-enoyloxy)nonanoic acid calcium salt; 9-((E)-4-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)oxiranylmethyl]tetrahydro-pyran-2-yl}-3-methyl-but-2-enoyloxy)nonanoic acid lithium salt; 9-({(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-({(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl)tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoyl}oxy)nonanoic acid; 9-(4-((2S,3R,4R,5S)-3,4-dihydroxy-5-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)-tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyloxy)nonanoic acid; 9-(4-{3,4-Dihydroxy-5-[3-(2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-3-methyl-but-2-enoyloxy)-nonanoic acid (Mupirocin); 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; 9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methyl-propyl]oxiran-2-yl]methyl]tetrahydropyran-2-yl]-3-methyl-but-2-enoyl]oxynonanoic 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; Nonanoic acid, 9-((3-methyl-1-oxo-4-(tetrahydro-3,4-dihydroxy-5-((3-(2-hydroxy-1-methylpropyl)oxiranyl)methyl)-2H-pyran-2-yl)-2-butenyl)oxy)-, (2S-(2alpha(E),3beta,4beta,5alpha(2R*,3R*(1R*,2R*))))-; rel-9-(((E)-4-((2S,3R,4R,5S)-3,4-Dihydroxy-5-(((2S,3S)-3-((2S,3S)-3-hydroxybutan-2-yl)oxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)-3-methylbut-2-enoyl)oxy)nonanoic acid
    Click to Show/Hide
Species Origin Pseudomonas fluorescens ...     Click to Show/Hide
Pseudomonas fluorescens
SuperKingdom: Bacteria
Phylum: Proteobacteria
Class: Gammaproteobacteria
Order: Pseudomonadales
Family: Pseudomonadaceae
Genus: Pseudomonas
Species: Pseudomonas fluorescens
Disease Bacterial infection [ICD-11: 1A00-1C4Z] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C26H44O9
PubChem CID
446596
Canonical SMILES
CC(C1C(O1)CC2COC(C(C2O)O)CC(=CC(=O)OCCCCCCCCC(=O)O)C)C(C)O
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
CAS Number
CAS 12650-69-0
ChEBI ID
CHEBI:7025
TTD Drug ID
D03JSJ
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Amoxicillin      Bacterial infection     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Mupirocin and amoxicillin-clavulanate were synergistic against 9 of 49 (18%) strains of methicillin-resistant and methicillin-susceptible Staphylococcus aureus and coagulase-negative staphylococci (CNS).
Target and Pathway
Target(s) Bacterial Isoleucyl-tRNA synthetase (Bact ileS)  Molecule Info  [3]
References
Reference 1 Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92.
Reference 2 In vitro activity of mupirocin and amoxicillin-clavulanate alone and in combination against staphylococci including those resistant to methicillin. Int J Antimicrob Agents. 2004 May;23(5):513-6.
Reference 3 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
 Download Picture         KEGG Link