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CHEBI:149836 - tigecycline

ChEBI IDCHEBI:149836
ChEBI Nametigecycline
Stars
DefinitionTetracycline in which the hydroxy group at position 5 and the methyl group at position 6 are replaced by hydrogen, and with a dimethylamino substituent and an (N-tert-butylglycyl)amino substituent at positions 7 and 9, respectively. A glycylcycline antibiotic, it has activity against a broad range of Gram-positive and Gram-negative bacteria, including tetracycline-resistant organisms. It is used for the intravenous treatment of complicated skin and skin structure infections caused by susceptible organisms.
Secondary ChEBI IDsCHEBI:29696, CHEBI:473970
Last Modified7 February 2018
DownloadsMolfile
FormulaC29H39N5O8
Net Charge0
Average Mass585.658
Monoisotopic Mass585.27986
SMILES[H][C@@]12Cc3c(N(C)C)cc(NC(=O)CNC(C)(C)C)c(O)c3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2
InChIInChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36,38-39,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1
InChIKeyFPZLLRFZJZRHSY-HJYUBDRYSA-N
Roles Classification
Biological Roles:
antibacterial drug  A drug used to treat or prevent bacterial infections.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
tigecycline (CHEBI:149836) has role antibacterial drug (CHEBI:36047)
tigecycline (CHEBI:149836) is a tertiary α-hydroxy ketone (CHEBI:139592)
tigecycline (CHEBI:149836) is a tetracyclines (CHEBI:26895)
tigecycline (CHEBI:149836) is conjugate base of tigecycline(1+) (CHEBI:142708)
Incoming Relation(s)
11a-hydroxytigecycline(1+) (CHEBI:142709) has functional parent tigecycline (CHEBI:149836)
tigecycline(1+) (CHEBI:142708) is conjugate acid of tigecycline (CHEBI:149836)
IUPAC Name 
(4S,4aS,5aR,12aS)-9-[(N-tert-butylglycyl)amino]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
Synonym  Source
(4S,4aS,5aR,12aS)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamideChemIDplus
Manual XrefsDatabases
2661DrugCentral
C12012KEGG COMPOUND
D01079KEGG DRUG
DB00560DrugBank
Registry NumbersSources
Reaxys:8379453Reaxys
CAS:220620-09-7ChemIDplus
CAS:220620-09-7KEGG COMPOUND
Citations