Structure Database (LMSD)
Common Name
Chlortetracycline
Systematic Name
Synonyms
LM ID
LMPK07000004
Formula
C22H23N2O8Cl
Exact Mass
Calculate m/z
478.114296
Status
Curated
3D model of Chlortetracycline
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
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
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
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
Admin
Created at
-
Updated at
12th Dec 2023