diprovocim-1   Click here for help

GtoPdb Ligand ID: 10341

Synonyms: compound 3 [PMID: 30272974]
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Diprovocim-1 is a highly potent, synthetic TLR1/TLR2 agonist [1]. It is structurally disctinct from other known natural or synthetic lipoprotein TLR agonists. Mechanistically it promotes the formation of TLR2 dimers and TLR2/TLR1 heterodimers in vitro [2]. The structure shown here was drawn from Morin et al. (2018) [1]. PubChem hold a record for Diprovocim that shows alternative stereochemistry (CID 134817267).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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 CDK toolkit. 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 12
Hydrogen bond donors 4
Rotatable bonds 20
Topological polar surface area 157.02
Molecular weight 908.43
XLogP 5.19
No. Lipinski's rules broken 3
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.

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Canonical SMILES O=C(c1ccc(cc1)C(=O)N1CC(C(C1)C(=O)NC1CC1c1ccccc1)C(=O)NC1CC1c1ccccc1)N1CC(C(C1)C(=O)NC1CC1c1ccccc1)C(=O)NC1CC1c1ccccc1
Isomeric SMILES O=C(c1ccc(cc1)C(=O)N1C[C@H]([C@@H](C1)C(=O)N[C@H]1C[C@@H]1c1ccccc1)C(=O)N[C@H]1C[C@@H]1c1ccccc1)N1C[C@H]([C@@H](C1)C(=O)N[C@H]1C[C@@H]1c1ccccc1)C(=O)N[C@H]1C[C@@H]1c1ccccc1
InChI InChI=1S/C56H56N6O6/c63-51(57-47-25-39(47)33-13-5-1-6-14-33)43-29-61(30-44(43)52(64)58-48-26-40(48)34-15-7-2-8-16-34)55(67)37-21-23-38(24-22-37)56(68)62-31-45(53(65)59-49-27-41(49)35-17-9-3-10-18-35)46(32-62)54(66)60-50-28-42(50)36-19-11-4-12-20-36/h1-24,39-50H,25-32H2,(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t39-,40-,41-,42-,43-,44-,45-,46-,47+,48+,49+,50+/m1/s1
InChI Key ABZBNXFGYUSVCJ-UYMKNZQYSA-N
References
1. Morin MD, Wang Y, Jones BT, Mifune Y, Su L, Shi H, Moresco EMY, Zhang H, Beutler B, Boger DL. (2018)
Diprovocims: A New and Exceptionally Potent Class of Toll-like Receptor Agonists.
J Am Chem Soc, 140 (43): 14440-14454. [PMID:30272974]
2. Su L, Wang Y, Wang J, Mifune Y, Morin MD, Jones BT, Moresco EMY, Boger DL, Beutler B, Zhang H. (2019)
Structural Basis of TLR2/TLR1 Activation by the Synthetic Agonist Diprovocim.
J Med Chem, 62 (6): 2938-2949. [PMID:30829478]
3. Wang Y, Su L, Morin MD, Jones BT, Mifune Y, Shi H, Wang KW, Zhan X, Liu A, Wang J et al.. (2018)
Adjuvant effect of the novel TLR1/TLR2 agonist Diprovocim synergizes with anti-PD-L1 to eliminate melanoma in mice.
Proc Natl Acad Sci USA, 115 (37): E8698-E8706. [PMID:30150374]