C004019   Click here for help

GtoPdb Ligand ID: 12146

Compound class: Synthetic organic
Comment: C004019 is a small-molecule PROTAC that selectively promotes tau protein degradation [1]. It was designed to reduce tau burden as a mechanism to improve cognitive functions in Alzheimer's disease and other tauopathies. C004019 binds simultaneously to tau and to the VHL E3-ligase to promote selective proteasomal degradation of tau.
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 21
Hydrogen bond donors 5
Rotatable bonds 31
Topological polar surface area 302.39
Molecular weight 1034.48
XLogP 1.81
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 O[C@H]1C[C@@H](N(C1)C(=O)[C@H](C(C)(C)C)NC(=O)COCCOCCOCCNC(=O)CN(c1nc(NCCc2cccs2)nc(n1)N1CCCN(CC1)C(=O)C)C)C(=O)NCc1ccc(cc1)c1scnc1C
Isomeric SMILES CN(CC(=O)NCCOCCOCCOCC(=O)N[C@H](C(=O)N1C[C@@H](O)C[C@@H]1C(=O)NCc1ccc(cc1)c1c(C)ncs1)C(C)(C)C)c1nc(NCCc2cccs2)nc(n1)N1CCCN(CC1)C(=O)C
InChI InChI=1S/C49H70N12O9S2/c1-33-42(72-32-53-33)36-12-10-35(11-13-36)28-52-44(66)39-27-37(63)29-61(39)45(67)43(49(3,4)5)54-41(65)31-70-25-24-69-23-22-68-21-16-50-40(64)30-58(6)47-55-46(51-15-14-38-9-7-26-71-38)56-48(57-47)60-18-8-17-59(19-20-60)34(2)62/h7,9-13,26,32,37,39,43,63H,8,14-25,27-31H2,1-6H3,(H,50,64)(H,52,66)(H,54,65)(H,51,55,56,57)/t37-,39+,43+/m0/s1
InChI Key IXTMPMLKABNFTQ-LLIFGLRNSA-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
Ligand families/groups PROTACs, molecular glues and other degraders
Database Links Click here for help
GtoPdb PubChem SID 472319268
PubChem CID 164889480
Search Google for chemical match using the InChIKey IXTMPMLKABNFTQ-LLIFGLRNSA-N
Search Google for chemicals with the same backbone IXTMPMLKABNFTQ
UniChem Compound Search for chemical match using the InChIKey IXTMPMLKABNFTQ-LLIFGLRNSA-N
UniChem Connectivity Search for chemical match using the InChIKey IXTMPMLKABNFTQ-LLIFGLRNSA-N