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lymecycline   Click here for help

GtoPdb Ligand ID: 10912

Synonyms: N-Lysinomethyltetracycline | tetracycline-L Methylene-Lysine | Tetralysal®
Approved drug
lymecycline is an approved drug (UK (1995))
Compound class: Synthetic organic
Comment: Lymecycline is a tetracycline-based broad-spectrum antibacterial [3]. It is substantially more soluble than tetracycline, so can be used at lower doses. Lymecycline also has anti-protozoal activity.

lymecycline is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 13
Hydrogen bond donors 9
Rotatable bonds 11
Topological polar surface area 242.98
Molecular weight 602.26
XLogP -1.85
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES N[C@H](C(=O)O)CCCCNCNC(=O)C1=C(O)[C@@]2([C@H]([C@@H](C1=O)N(C)C)C[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O
Isomeric SMILES N[C@H](C(=O)O)CCCCNCNC(=O)C1=C(O)[C@@]2([C@H]([C@@H](C1=O)N(C)C)C[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O
InChI InChI=1S/C29H38N4O10/c1-28(42)13-7-6-9-17(34)18(13)22(35)19-14(28)11-15-21(33(2)3)23(36)20(25(38)29(15,43)24(19)37)26(39)32-12-31-10-5-4-8-16(30)27(40)41/h6-7,9,14-16,21,31,34-35,38,42-43H,4-5,8,10-12,30H2,1-3H3,(H,32,39)(H,40,41)/t14-,15-,16-,21-,28+,29-/m0/s1
InChI Key PZTCVADFMACKLU-UEPZRUIBSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. UK MHRA (1995)
IUPAC Name Click here for help
(2S)-6-[[[(4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carbonyl]amino]methylamino]-2-aminohexanoic acid
International Nonproprietary Names Click here for help
INN number INN
1679 lymecycline
Synonyms Click here for help
N-Lysinomethyltetracycline | tetracycline-L Methylene-Lysine | Tetralysal®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Lymecycline
Other databases
CAS Registry No. 992-21-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL2103929
DrugBank Ligand DB00256
GtoPdb PubChem SID 405560353
PubChem CID 54707177
Search Google for chemical match using the InChIKey PZTCVADFMACKLU-UEPZRUIBSA-N
Search Google for chemicals with the same backbone PZTCVADFMACKLU
Search PubMed clinical trials lymecycline
Search PubMed titles lymecycline
Search PubMed titles/abstracts lymecycline
UniChem Compound Search for chemical match using the InChIKey PZTCVADFMACKLU-UEPZRUIBSA-N
UniChem Connectivity Search for chemical match using the InChIKey PZTCVADFMACKLU-UEPZRUIBSA-N

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MedChemExpress
Lymecycline (links to external site)
Cat. No. HY-106339
(Same CID)