CHEBI:27902 - tetracycline

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ChEBI Name tetracycline
ChEBI ID CHEBI:27902
Definition A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45729, CHEBI:9474, CHEBI:26894
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Formula C22H24N2O8
Net Charge 0
Average Mass 444.43460
Monoisotopic Mass 444.153
InChI InChI=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
InChIKey OFVLGDICTFRJMM-WESIUVDSSA-N
SMILES [H][C@@]12C[C@@]3([H])C(C(=O)c4c(O)cccc4[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C
Metabolite of Species Details
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
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.
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal 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.
(via tetracyclines )
Application(s): 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.
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ChEBI Ontology
Outgoing 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 conjugate acid of tetracycline zwitterion (CHEBI:77932)
tetracycline (CHEBI:27902) is conjugate acid of tetracycline(1−) (CHEBI:71392)
Incoming 11a-hydroxytetracycline (CHEBI:134017) has functional parent tetracycline (CHEBI:27902)
tetracycline zwitterion (CHEBI:77932) is conjugate base of tetracycline (CHEBI:27902)
tetracycline(1−) (CHEBI:71392) is conjugate base 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 Sources
tetracycline ChemIDplus
tetracyclinum ChemIDplus
Synonyms Sources
(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-naphthacenecarboxamide ChemIDplus
Abramycin ChemIDplus
Achromycin ChEBI
Anhydrotetracycline DrugBank
Deschlorobiomycin ChemIDplus
Liquamycin ChemIDplus
Tetracyclin ChEBI
Tetracycline KEGG COMPOUND
TETRACYCLINE PDBeChem
tétracycline ChEBI
Tetrazyklin ChEBI
Tsiklomitsin ChemIDplus
Manual Xrefs Databases
1739 VSDB
2611 DrugCentral
C06570 KEGG COMPOUND
CPD0-1414 MetaCyc
D00201 KEGG DRUG
DB00759 DrugBank
TAC PDBeChem
Tetracycline Wikipedia
US2699054 Patent
US2712517 Patent
US2886595 Patent
US3005023 Patent
US3019173 Patent
US3301899 Patent
View more database links
Registry Numbers Types Sources
1103368 Gmelin Registry Number Gmelin
2230417 Beilstein Registry Number Beilstein
2230417 Reaxys Registry Number Reaxys
60-54-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11061623 PubMed citation Europe PMC
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Last Modified
19 September 2018