TETRACYCLINE

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC A01AB13 D06AA04 J01AA07 S01AA09 S02AA08 S03AA02
UNII F8VB5M810T
EPA CompTox DTXSID7023645

Structure

InChI Key OFVLGDICTFRJMM-WESIUVDSSA-N
Smiles CN(C)[C@@H]1C(O)=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)cccc4[C@@](C)(O)[C@H]3C[C@@H]12
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H24N2O8
Molecular Weight 444.44
AlogP -0.21
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 6.0
Number of Rotational Bond 2.0
Polar Surface Area 181.62
Molecular species ZWITTERION
Aromatic Rings 1.0
Heavy Atoms 32.0

Bioactivity

Mechanism of Action Action Reference
Bacterial 70S ribosome inhibitor INHIBITOR FDA PubMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Metallo protease Metallo protease MAM clan Metallo protease M10A subfamily
- - - - 100
Enzyme Transferase
- - - - 10
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Purine receptor
- - - - 2
Other cytosolic protein
- 4580 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 22
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 13200 - - 10
Unclassified protein
- 4580 - - 40
Assay Description Organism Bioactivity Reference
Inhibition of purified telomerase of Euplotes aediculatus at 50 uM Euplotes aediculatus 0.0 %
Inhibition of telomerase after assembly using recombinant Tetraymena thermophilia TR and TERT at 50 uM Tetrahymena thermophila 0.0 %
Inhibition of telomerase before assembly using recombinant Tetraymena thermophilia TR and TERT at 50 uM Tetrahymena thermophila 0.0 %
Inhibition of human telomerase before assembly using recombinant hTR and hTERT at 50 uM Homo sapiens 10.0 %
Antiproliferative effect against primary human osteoblasts assessed as BrdU incorporation into DNA after 48 hrs Homo sapiens 180.0 ug.mL-1
Antiproliferative effect against MG63 cells assessed as BrdU incorporation into DNA after 48 hrs after 48 hrs Homo sapiens 180.0 ug.mL-1
Antiproliferative effect against HeLa cells after 48 hrs Homo sapiens 400.0 ug.mL-1
Antimicrobial activity against Escherichia coli NCIM2574 by broth microdilution method Escherichia coli 4.0 ug.mL-1
Antimicrobial activity against Staphylococcus aureus NCIM2122 by broth microdilution method Staphylococcus aureus 8.0 ug.mL-1
Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 Plasmodium falciparum 5.385 ug.mL-1
Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum D6 Plasmodium falciparum D6 3.365 ug.mL-1
Antibacterial activity against Staphylococcus aureus ATCC 6535 after 48 hrs by microplate assay Staphylococcus aureus 0.15 ug.mL-1
Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 33591 after 48 hrs by microplate assay Staphylococcus aureus 0.15 ug.mL-1
Antimalarial activity after 96 hrs against Plasmodium falciparum Dd2 by [3H]hypoxanthine uptake Plasmodium falciparum 397.1 nM
Antimalarial activity after 96hrs against Plasmodium falciparum 7G8 by [3H]hypoxanthine uptake Plasmodium falciparum 696.7 nM
Antimalarial activity after 96 hrs against azithromycin-resistant Plasmodium falciparum Dd2 by [3H]hypoxanthine uptake Plasmodium falciparum 323.9 nM
Antimalarial activity after 96 hrs against azithromycin-resistant Plasmodium falciparum 7G8 by [3H]hypoxanthine uptake Plasmodium falciparum 364.7 nM
Displacement of [3H]PSB0413 from human platelet P2Y12 receptor at 10 uM Homo sapiens 2.0 %
Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 43300 after 18 hrs by broth dilution assay Staphylococcus aureus 0.2 ug.mL-1
Antibacterial activity against vancomycin-resistant Enterococcus faecalis ATCC 51299 after 18 hrs by broth dilution assay Enterococcus faecalis 0.7 ug.mL-1
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 10.4 %
Antibacterial activity against Escherichia coli after 24 hrs by NCCLS microdilution method Escherichia coli 0.09 ug.mL-1
Antibacterial activity against Pseudomonas aeruginosa after 24 hrs by NLCCS microdilution method Pseudomonas aeruginosa 0.06 ug.mL-1
Antibacterial activity against Staphylococcus aureus after 24 hrs by NLCCS microdilution method Staphylococcus aureus 0.12 ug.mL-1
Antibacterial activity against Staphylococcus epidermidis after 24 hrs by NLCCS microdilution method Staphylococcus epidermidis 0.08 ug.mL-1
Antimicrobial activity against Plasmodium falciparum Plasmodium falciparum 0.0 nM
Inhibition of MexAB-OprM efflux pump expression in Pseudomonas aeruginosa TNP090 mutant harboring las and rhl gene at 0.03 ug/ml by Cat-2,3-diO reporter gene assay relative to untreated control Pseudomonas aeruginosa 94.0 %
Inhibition of MexAB-OprM efflux pump expression in Pseudomonas aeruginosa TNP090 mutant harboring las and rhl gene at 0.016 ug/ml by Cat-2,3-diO reporter gene assay relative to untreated control Pseudomonas aeruginosa 103.0 %
Inhibition of MexAB-OprM efflux pump expression in Pseudomonas aeruginosa TNP090 mutant harboring las and rhl gene at 0.125 ug/ml by Cat-2,3-diO reporter gene assay relative to untreated control Pseudomonas aeruginosa 51.0 %
Inhibition of MexAB-OprM efflux pump expression in Pseudomonas aeruginosa TNP090 mutant harboring las and rhl gene at 0.06 ug/ml by Cat-2,3-diO reporter gene assay relative to untreated control Pseudomonas aeruginosa 69.0 %
Antibacterial activity against Escherichia coli EPI300 harboring plasmid GEM-T expressing tet(40) gene after 16 hrs Escherichia coli 60.0 ug.mL-1
Antimycobacterial activity against Mycobacterium smegmatis assessed as growth inhibition in mid-logarithmic phase by spectrophotometry Mycobacterium smegmatis 410.0 nM
Antimycobacterial activity against Mycobacterium smegmatis by GFP-based fluorescence assay Mycobacterium smegmatis 330.0 nM
Inhibition of acrAB AcrAB-TolC in Escherichia coli K-12 3-AG100 overexpressing acrAB AcrAB-TolC assessed as [3H]TMG accumulation at 800 uM by scintillation counter method Escherichia coli K-12 27.0 %
Inhibition of protein synthesis in Escherichia coli S30 extract by coupled transcription/translation assay Escherichia coli 2.0 ug.mL-1
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 22.1 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 29.5 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 51.1 %
Inhibition of beta-haematin formation by microplate reader analysis relative to hemin None 4.0 equiv
Inhibition of MMP9 in inflamed tissue isolated from chronic periodontitis patient at 500 ug/l after 15 to 30 mins by gelatin zymographic method relative to control Homo sapiens 100.0 %
Inhibition of MMP2 in inflamed tissue isolated from chronic periodontitis patient at 500 ug/l after 15 to 30 mins by gelatin zymographic method relative to control Homo sapiens 100.0 %
Inhibition of Dicer mediated biotinylated pre-miRNA-21 (unknown origin) maturation at 1 mM measured after 15 mins by cat-ELCCA relative to control Not specified 40.0 %

Related Entries

Cross References

Resources Reference
ChEBI 77932
ChEMBL CHEMBL1440
DrugBank DB00759
DrugCentral 2611
FDA SRS F8VB5M810T
Human Metabolome Database HMDB0014897
Guide to Pharmacology 10927
KEGG C06570
PDB TAC
SureChEMBL SCHEMBL3098
ZINC ZINC000084441937
CONTENTS