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teixobactin   Click here for help

GtoPdb Ligand ID: 10972

Synonyms: compound of formula II [WO2014089053A1] | N-[N-Methyl-D-Phe-Ile-Ser-D-Gln-D-aIle-Ile-Ser-]cyclo[D-Thr*-Ala-[3-(2-iminoimidazolidine-4beta-yl)-Ala-]-Ile-]
Compound class: Natural product
Comment: Teixobactin is a small natural peptide produced by soil-dwelling bacteria [1-2]. It blocks bacterial cell wall synthesis [3], but using a different mechanism to other cell wall inhibitor antibacterial drugs.
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 30
Hydrogen bond donors 16
Rotatable bonds 39
Topological polar surface area 463.29
Molecular weight 1241.71
XLogP 1
No. Lipinski's rules broken 3

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 CC[C@@H]([C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H]1[C@H](C)OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)C)C[C@H]1CN=C(N1)N)[C@H](CC)C)CO)[C@H](CC)C)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](Cc1ccccc1)NC)CO)CCC(=O)N)C
Isomeric SMILES CC[C@@H]([C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H]1[C@H](C)OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)C)C[C@H]1CN=C(N1)N)[C@H](CC)C)CO)[C@H](CC)C)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](Cc1ccccc1)NC)CO)CCC(=O)N)C
InChI InChI=1S/C58H95N15O15/c1-12-28(5)42(70-49(79)37(61-11)23-34-19-17-16-18-20-34)53(83)67-39(26-74)51(81)65-36(21-22-41(59)76)48(78)69-44(30(7)14-3)55(85)71-43(29(6)13-2)54(84)68-40(27-75)52(82)73-46-33(10)88-57(87)45(31(8)15-4)72-50(80)38(24-35-25-62-58(60)64-35)66-47(77)32(9)63-56(46)86/h16-20,28-33,35-40,42-46,61,74-75H,12-15,21-27H2,1-11H3,(H2,59,76)(H,63,86)(H,65,81)(H,66,77)(H,67,83)(H,68,84)(H,69,78)(H,70,79)(H,71,85)(H,72,80)(H,73,82)(H3,60,62,64)/t28-,29-,30-,31-,32-,33-,35-,36+,37+,38-,39-,40-,42-,43-,44+,45-,46+/m0/s1
InChI Key LMBFAGIMSUYTBN-MPZNNTNKSA-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 Natural product
IUPAC Name Click here for help
(2R)-N-[(2R,3S)-1-[[(2S,3S)-1-[[(2S)-1-[[(3S,6S,9S,12R,13S)-6-[[(5S)-2-amino-4,5-dihydro-1H-imidazol-5-yl]methyl]-3-[(2S)-butan-2-yl]-9,13-dimethyl-2,5,8,11-tetraoxo-1-oxa-4,7,10-triazacyclotridec-12-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]-2-[[(2S)-3-hydroxy-2-[[(2S,3S)-3-methyl-2-[[(2R)-2-(methylamino)-3-phenylpropanoyl]amino]pentanoyl]amino]propanoyl]amino]pentanediamide
Synonyms Click here for help
compound of formula II [WO2014089053A1] | N-[N-Methyl-D-Phe-Ile-Ser-D-Gln-D-aIle-Ile-Ser-]cyclo[D-Thr*-Ala-[3-(2-iminoimidazolidine-4beta-yl)-Ala-]-Ile-]
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Teixobactin
Other databases
BindingDB Ligand 237161
CAS Registry No. 1613225-53-8 (source: PubChem)
ChEBI CHEBI:84192
ChEMBL Ligand CHEMBL3977597
GtoPdb PubChem SID 405560413
PubChem CID 86341926
Search Google for chemical match using the InChIKey LMBFAGIMSUYTBN-MPZNNTNKSA-N
Search Google for chemicals with the same backbone LMBFAGIMSUYTBN
UniChem Compound Search for chemical match using the InChIKey LMBFAGIMSUYTBN-MPZNNTNKSA-N
UniChem Connectivity Search for chemical match using the InChIKey LMBFAGIMSUYTBN-MPZNNTNKSA-N