zifanocycline   Click here for help

GtoPdb Ligand ID: 12794

Synonyms: KBP-7072
Compound class: Synthetic organic
Comment: Zifanocycline is an aminomethylcycline (tetracycline derivative) with broad-spectrum antibacterial activity [3]. We show the chemical structure provided by PubChem, but note that this is not an exact match for the CAS number assigned in the WHO INN record for this drug.
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 11
Hydrogen bond donors 5
Rotatable bonds 5
Topological polar surface area 167.87
Molecular weight 552.62
XLogP 0.55
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 CN(C)C1=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C(C(=C1)CN5CC6CC6C5)O)O)O)O)C(=O)N)N(C)C
Isomeric SMILES CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=C(C(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)CN5CC6CC6C5)N(C)C
InChI InChI=1S/C29H36N4O7/c1-31(2)18-8-15(11-33-9-13-5-14(13)10-33)23(34)20-16(18)6-12-7-17-22(32(3)4)25(36)21(28(30)39)27(38)29(17,40)26(37)19(12)24(20)35/h8,12-14,17,22,34-35,38,40H,5-7,9-11H2,1-4H3,(H2,30,39)/t12-,13?,14?,17-,22-,29-/m0/s1
InChI Key LBKXOQRVWDAQSX-OMBSCLNISA-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
IUPAC Name Click here for help
(4S,4aS,5aR,12aR)-9-(3-azabicyclo[3.1.0]hexan-3-ylmethyl)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
11805 zifanocycline
Synonyms Click here for help
KBP-7072
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Zifanocycline
Other databases
CAS Registry No. 1420294-56-9 (source: Scifinder)
GtoPdb PubChem SID 483123342
PubChem CID 71243332
Search Google for chemical match using the InChIKey LBKXOQRVWDAQSX-OMBSCLNISA-N
Search Google for chemicals with the same backbone LBKXOQRVWDAQSX
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UniChem Compound Search for chemical match using the InChIKey LBKXOQRVWDAQSX-OMBSCLNISA-N
UniChem Connectivity Search for chemical match using the InChIKey LBKXOQRVWDAQSX-OMBSCLNISA-N