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CHEBI:27902 - tetracycline

ChEBI IDCHEBI:27902
ChEBI Nametetracycline
Stars
DefinitionA broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.
Secondary ChEBI IDsCHEBI:9474, CHEBI:26894, CHEBI:45729
Last Modified3 June 2025
SubmitterSteve
DownloadsMolfile
FormulaC22H24N2O8
Net Charge0
Average Mass444.440
Monoisotopic Mass444.15327
SMILES[H][C@]12C[C@@]3([H])[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C1C(=O)c1c(O)cccc1[C@@]2(C)O
InChIInChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
InChIKeyOFVLGDICTFRJMM-WESIUVDSSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Roles Classification
Biological Roles:
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antibacterial drug  A drug used to treat or prevent bacterial infections.
protein synthesis inhibitor  A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
tetracycline (CHEBI:27902) has role Escherichia coli metabolite (CHEBI:76971)
tetracycline (CHEBI:27902) has role antibacterial drug (CHEBI:36047)
tetracycline (CHEBI:27902) has role antimicrobial agent (CHEBI:33281)
tetracycline (CHEBI:27902) has role antiprotozoal drug (CHEBI:35820)
tetracycline (CHEBI:27902) has role protein synthesis inhibitor (CHEBI:48001)
tetracycline (CHEBI:27902) is a tertiary α-hydroxy ketone (CHEBI:139592)
tetracycline (CHEBI:27902) is a tetracyclines (CHEBI:26895)
tetracycline (CHEBI:27902) is tautomer of tetracycline zwitterion (CHEBI:77932)
Incoming Relation(s)
11a-hydroxytetracycline (CHEBI:134017) has functional parent tetracycline (CHEBI:27902)
tetracycline zwitterion (CHEBI:77932) is tautomer of tetracycline (CHEBI:27902)
IUPAC Name 
(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
INNs  Source
tetracyclinumChemIDplus
tetracyclineChemIDplus
Synonyms  Source
TetracyclineKEGG COMPOUND
(4S,4aS,5aS,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamideChemIDplus
DeschlorobiomycinChemIDplus
TsiklomitsinChemIDplus
AbramycinChemIDplus
LiquamycinChemIDplus
Brand Name  Source
AchromycinChEBI
Manual XrefsDatabases
C06570KEGG COMPOUND
TACPDBeChem
D00201KEGG DRUG
DB00759DrugBank
US2699054Patent
US2712517Patent
US2886595Patent
US3005023Patent
US3019173Patent
US3301899Patent
TetracyclineWikipedia
CPD0-1414MetaCyc
2611DrugCentral
1739VSDB
Registry NumbersSources
Gmelin:1103368Gmelin
Reaxys:2230417Reaxys
CAS:60-54-8ChemIDplus
CAS:60-54-8KEGG COMPOUND
Citations