loading...| Preferred Name |
mupirocin |
| Synonyms |
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 Pseudomonic acid A mupirocinum Centany mupirocin Bactroban mupirocina mupirocine |
| Definitions |
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. |
| ID |
http://purl.obolibrary.org/obo/CHEBI_7025 |
| charge |
0 |
| database_cross_reference |
Wikipedia:Mupirocin Patent:US4071536 DrugBank:DB00410 PMID:23535880 PMID:3101012 Patent:US3977943 HMDB:HMDB0014554 PMID:22500807 KEGG:D01076 Drug_Central:1857 Patent:DE2227739 PMID:23337107 PMID:23543635 PMID:24625190 CAS:12650-69-0 |
| definition |
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. |
| formula |
C26H44O9 |
| has role |
http://purl.obolibrary.org/obo/CHEBI_36047 |
| has_alternative_id |
CHEBI:44038 |
| has_exact_synonym |
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 |
| has_obo_namespace |
chebi_ontology |
| has_related_synonym |
Pseudomonic acid A mupirocinum Centany mupirocin Bactroban mupirocina mupirocine |
| id |
CHEBI:7025 |
| in_subset | |
| 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 |
| is conjugate acid of | |
| label |
mupirocin |
| mass |
500.62220 |
| monoisotopicmass |
500.29853 |
| notation |
CHEBI:7025 |
| prefLabel |
mupirocin |
| smiles |
C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]1CO[C@@H](CC(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O |
| treeView |
http://purl.obolibrary.org/obo/CHEBI_46942 http://purl.obolibrary.org/obo/CHEBI_25384 http://purl.obolibrary.org/obo/CHEBI_51737 http://purl.obolibrary.org/obo/CHEBI_35681 |
| subClassOf |
http://purl.obolibrary.org/obo/CHEBI_46942 http://purl.obolibrary.org/obo/CHEBI_25384 http://purl.obolibrary.org/obo/CHEBI_51737 http://purl.obolibrary.org/obo/CHEBI_35681 |