tunicamycin   Click here for help

GtoPdb Ligand ID: 13510

Synonyms: tunicamycin A | tunicamycin B2 | tunicamycin V
PDB Ligand
Compound class: Natural product
Comment: Tunicamycin is a nucleoside antibacterial compound, originally isolated from culture broth of Streptomyces lysosuperificus [1]. It inhibits phospho-N-acetylmuramoyl-pentapeptide-transferase (MraY, translocase I), an essential enzyme in bacterial peptidoglycan biosynthesis.
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 20
Hydrogen bond donors 11
Rotatable bonds 22
Topological polar surface area 306.37
Molecular weight 830.92
XLogP 2.44
No. Lipinski's rules broken 4

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)CCCCCCCCC/C=C/C(=O)N[C@@H]1[C@H]([C@H]([C@@H](C[C@H]([C@@H]2[C@H]([C@H]([C@H](N3C=CC(=O)NC3=O)O2)O)O)O)O[C@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)NC(=O)C)O)O
Isomeric SMILES CC(C)CCCCCCCCC/C=C/C(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)NC(=O)C)C[C@H]([C@@H]3[C@H]([C@H]([C@@H](O3)N4C=CC(=O)NC4=O)O)O)O)O)O
InChI InChI=1S/C38H62N4O16/c1-19(2)13-11-9-7-5-4-6-8-10-12-14-24(46)40-27-31(51)28(48)22(55-37(27)58-36-26(39-20(3)44)30(50)29(49)23(18-43)56-36)17-21(45)34-32(52)33(53)35(57-34)42-16-15-25(47)41-38(42)54/h12,14-16,19,21-23,26-37,43,45,48-53H,4-11,13,17-18H2,1-3H3,(H,39,44)(H,40,46)(H,41,47,54)/b14-12+/t21-,22-,23-,26-,27-,28+,29-,30-,31-,32+,33-,34-,35-,36-,37+/m1/s1
InChI Key MEYZYGMYMLNUHJ-DIRMKAHISA-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
(E)-N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[(2R)-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]-13-methyltetradec-2-enamide
Synonyms Click here for help
tunicamycin A | tunicamycin B2 | tunicamycin V
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Tunicamycin
Other databases
BindingDB Ligand 50537412
CAS Registry No. 66054-36-2 (source: Scifinder)
ChEBI CHEBI:64250
ChEMBL Ligand CHEMBL4534172
GtoPdb PubChem SID 500839920
PubChem CID 11104835
RCSB PDB Ligand 9LH
Search Google for chemical match using the InChIKey MEYZYGMYMLNUHJ-DIRMKAHISA-N
Search Google for chemicals with the same backbone MEYZYGMYMLNUHJ
UniChem Compound Search for chemical match using the InChIKey MEYZYGMYMLNUHJ-DIRMKAHISA-N
UniChem Connectivity Search for chemical match using the InChIKey MEYZYGMYMLNUHJ-DIRMKAHISA-N
Wikipedia Tunicamycin