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CHEBI:149836 - tigecycline

Default Structure
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.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antibacterial drug  A drug used to treat or prevent bacterial infections.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
ChEBI Ontology
Outgoing Relation(s)
tigecycline (CHEBI:149836) has role antibacterial agent (CHEBI:33282)
tigecycline (CHEBI:149836) has role antibacterial drug (CHEBI:36047)
tigecycline (CHEBI:149836) has role antiinfective agent (CHEBI:35441)
tigecycline (CHEBI:149836) has role antineoplastic agent (CHEBI:35610)
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
INN  Source
tigeciclinaWHO MedNet
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
Brand Name  Source
Tigecycline accordChEMBL
Manual XrefsDatabases
2661DrugCentral
C12012KEGG COMPOUND
D01079KEGG DRUG
DB00560DrugBank
Registry NumbersSources
Reaxys:8379453Reaxys
CAS:220620-09-7ChemIDplus
CAS:220620-09-7KEGG COMPOUND
Citations