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CHEBI:50845 - doxycycline

Default Structure
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.
antibacterial drug  A drug used to treat or prevent bacterial infections.
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.
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.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
immunomodulator  Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
antibacterial drug  A drug used to treat or prevent bacterial infections.
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.
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
doxiciclinaChemIDplus
doxycyclineKEGG DRUG
doxycyclinumChemIDplus
Synonyms  Source
(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
5-hydroxy-α-6-deoxytetracyclineChemIDplus
6α-deoxy-5-oxytetracyclineChemIDplus
DoxycyclinChEBI
DoxycyclineKEGG COMPOUND
doxycycline (anhydrous)ChemIDplus
Brand Names  Source
JenacyclinDrugBank
SupracyclinDrugBank
VibramycinDrugBank
Manual XrefsDatabases
10469369ChemSpider
1840VSDB
961DrugCentral
C00017127KNApSAcK
C06973KEGG COMPOUND
CPD-19256MetaCyc
D07876KEGG DRUG
DB00254DrugBank
DoxycyclineWikipedia
DXTPDBeChem
HMDB0014399HMDB
LMPK07000001LIPID MAPS
US3019260Patent
US3200149Patent
Registry NumbersSources
Reaxys:3041790Reaxys
CAS:564-25-0KEGG COMPOUND
CAS:564-25-0ChemIDplus
Citations