Structure Database (LMSD)

Common Name
Chlortetracycline
Systematic Name
Synonyms
LM ID
LMPK07000004
Formula
C22H23N2O8Cl
Exact Mass
Calculate m/z
478.114296
Status
Curated


Classification

Biological Context

Chlortetracycline is a broad-spectrum antibiotic originally isolated from S. aureofaciens.1,2 It inhibits growth of both Gram-positive and Gram-negative bacteria at a range of 0.1-100 μg/ml against A. aerogenes, D. pneumoniae, E. coli, K. pneumoniae, P. morganii, and several species of Haemophilus, Neisseria, Salmonella, and Staphylococcus.2 Chlortetracycline protects mice from infection by various strains of S. aureus with protective doses (PD50s) of 0.2-7.5 mg/kg, and from infection by E. coli (PD50 = 3 mg/kg) and K. pneumoniae (PD50 = 75 mg/kg).3 It acts by inhibiting protein synthesis, and it binds to a single site on the 30S ribosome subunit.1 Chlortetracycline is an ionophore and is selective for calcium over sodium, potassium, magnesium, strontium, and barium.4 It transports calcium from an aqueous phase into an organic phase environment or into multilamellar vesicles. Chlortetracycline is also a fluorescent dye that can be used to monitor calcium flux.5

This information has been provided by Cayman Chemical

References

2. White, J.R., and Pearce, F.L. Characterization of chlortetracycline (aureomycin) as a calcium ionophore. Biochemistry 21(24), 6309-6312 (1982).
3. Paine, T.F., Jr., Collins, H.S., and Finland, M. Bacteriologic studies on aureomycin. J. Bacteriol. 56(4), 489-497 (1948).
4. Cacciapuoti, A., Moss, E., Jr., Menzel, F., Jr., et al. In vitro and in vivo characterization of novel 8-methoxy derivatives of chlortetracycline. J. Antibiot. (Tokyo) 40(10), 1426-1430 (1987).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Kitasatospora aureofaciens (#1894)
Actinomycetes (#1760)
Some historical notes on chlortetracycline.,
Rev Infect Dis, 1985
Pubmed ID: 3903946

String Representations

InChiKey (Click to copy)
CYDMQBQPVICBEU-XRNKAMNCSA-N
InChi (Click to copy)
InChI=1S/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31)/t7-,8-,15-,21-,22-/m0/s1
SMILES (Click to copy)
[C@@]12([H])C[C@@]3([H])C(C(=O)C4C(=C(Cl)C=CC=4O)[C@]3(O)C)=C(O)[C@]1(O)C(=O)C(=C(O)[C@H]2N(C)C)C(=O)N

Other Databases

Wikipedia
KEGG ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 4
Aromatic Rings 1
Rotatable Bonds 2
Van der Waals Molecular Volume 415.23
Topological Polar Surface Area 181.62
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 10
logP 1.01
Molar Refractivity 115.57

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Created at
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Updated at
12th Dec 2023