tetracycline   Click here for help

GtoPdb Ligand ID: 10927

Synonyms: achromycin | Ala-Tet® | Brodspec® | NSC-108579 | Panmycin® | Sumycin® | TCN
Approved drug
tetracycline is an approved drug (FDA (1953), UK (2001))
Compound class: Synthetic organic
Comment: Tetracycline is a long-used oral antibiotic. It has broad spectrum activity against aerobic and anaerobic bacteria, both Gram-negative and Gram-positive. Pseudomonas aeruginosa and Proteus spp. have natural resistance to tetracyclines. Acquired resistance to tetracycline is now commonplace.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 2
Topological polar surface area 181.62
Molecular weight 444.15
XLogP 0.26
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1C[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O)O)C(=O)N)C
Isomeric SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1C[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O)O)C(=O)N)C
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/h4-6,9-10,15,25-26,29,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
InChI Key NWXMGUDVXFXRIG-WESIUVDSSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1953), UK (2001))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
298 tetracycline
Synonyms Click here for help
achromycin | Ala-Tet® | Brodspec® | NSC-108579 | Panmycin® | Sumycin® | TCN
Database Links Click here for help
BindingDB Ligand 50237605
CAS Registry No. 60-54-8 (source: WHO INN record)
ChEMBL Ligand ChEMBL1440
DrugBank Ligand DB00759
GtoPdb PubChem SID 405560368
PubChem CID 54675776
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