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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:
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.
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
protein synthesis inhibitor  A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
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.
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal 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
tetracyclineChemIDplus
tetracyclinumChemIDplus
Synonyms  Source
(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
AbramycinChemIDplus
AnhydrotetracyclineDrugBank
DeschlorobiomycinChemIDplus
LiquamycinChemIDplus
TetracyclinChEBI
Brand Name  Source
AchromycinChEBI
Manual XrefsDatabases
1739VSDB
2611DrugCentral
C06570KEGG COMPOUND
CPD0-1414MetaCyc
D00201KEGG DRUG
DB00759DrugBank
TACPDBeChem
TetracyclineWikipedia
US2699054Patent
US2712517Patent
US2886595Patent
US3005023Patent
US3019173Patent
US3301899Patent
Registry NumbersSources
Gmelin:1103368Gmelin
Reaxys:2230417Reaxys
CAS:60-54-8KEGG COMPOUND
CAS:60-54-8ChemIDplus
Citations