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CHEBI:50845 - doxycycline

ChEBI IDCHEBI:50845
ChEBI Namedoxycycline
Stars
DefinitionTetracycline in which the 5β-hydrogen is replaced by a hydroxy group, while the 6α-hydroxy group is replaced by hydrogen. A semi-synthetic tetracycline antibiotic, it is used to inhibit bacterial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with chronic obstructive pulmonary disease (COPD), and adult periodontitis.
Secondary ChEBI IDsCHEBI:4713, CHEBI:42135
Last Modified29 September 2021
SubmitterKirill Degtyarenko
DownloadsMolfile
FormulaC22H24N2O8
Net Charge0
Average Mass444.440
Monoisotopic Mass444.15327
SMILES[H][C@@]12C(=C(O)[C@]3(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]3([H])[C@H]1O)C(=O)c1c(O)cccc1[C@@H]2C
InChIInChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1
InChIKeyJBIWCJUYHHGXTC-AKNGSSGZSA-N
Wikipedia
Roles Classification
Biological Roles:
immunomodulator  Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
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.
Applications:
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
immunomodulator  Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
doxycycline (CHEBI:50845) has role anti-inflammatory agent (CHEBI:67079)
doxycycline (CHEBI:50845) has role antibacterial drug (CHEBI:36047)
doxycycline (CHEBI:50845) has role antimalarial (CHEBI:38068)
doxycycline (CHEBI:50845) has role geroprotector (CHEBI:176497)
doxycycline (CHEBI:50845) has role immunomodulator (CHEBI:50846)
doxycycline (CHEBI:50845) is a tetracyclines (CHEBI:26895)
Incoming Relation(s)
doxycycline HCl (CHEBI:652992) has part doxycycline (CHEBI:50845)
doxycycline monohydrate (CHEBI:60648) has part doxycycline (CHEBI:50845)
IUPAC Name 
(4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
INNs  Source
doxycyclineKEGG DRUG
doxycyclinumChemIDplus
doxiciclinaChemIDplus
Synonyms  Source
DoxycyclineKEGG COMPOUND
(4S,4AR,5S,5AR,6R,12AS)-4-(DIMETHYLAMINO)-3,5,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDEPDBeChem
DoxycyclinChEBI
doxycycline (anhydrous)ChemIDplus
5-hydroxy-α-6-deoxytetracyclineChemIDplus
6α-deoxy-5-oxytetracyclineChemIDplus
Brand Names  Source
VibramycinDrugBank
JenacyclinDrugBank
SupracyclinDrugBank
Manual XrefsDatabases
C06973KEGG COMPOUND
DXTPDBeChem
D07876KEGG DRUG
DB00254DrugBank
US3019260Patent
US3200149Patent
DoxycyclineWikipedia
C00017127KNApSAcK
961DrugCentral
1840VSDB
10469369ChemSpider
CPD-19256MetaCyc
HMDB0014399HMDB
LMPK07000001LIPID MAPS
Registry NumbersSources
Reaxys:3041790Reaxys
CAS:564-25-0KEGG COMPOUND
CAS:564-25-0ChemIDplus
Citations