NAMPT PROTAC B4   Click here for help

GtoPdb Ligand ID: 12271

Synonyms: compound 5 [PMID: 36442664]
Compound class: Synthetic organic
Comment: This compound is a PROTAC that targets the NAD+ synthesising enzyme nicotinamide phosphoribosyltransferase (NAMPT) to the ubiquitin-proteasome system for degradation [1]. Its NAMPT-binding warhead (inhibitor M049-0244 [2]) is a fluorescent ligand that allows monitoring of degradation within cells, and it uses a VHL ligand to engage the E3 ligase. Reducing intracellular NAD+ levels is an approach that is exploited to inhibit the expansion of rapidly proliferating cancer cells.
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 15
Hydrogen bond donors 5
Rotatable bonds 30
Topological polar surface area 245.85
Molecular weight 1051.54
XLogP 9.43
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 CCCn1c2cc(ccc2nc(c1=O)c1ccc(cc1)C(=O)NCc1cccnc1)NC(=O)CCCCCCCCCCC(=O)N[C@@H](C(C)(C)C)C(=O)N1C[C@@H](C[C@H]1C(=O)N[C@H](c1ccc(cc1)c1scnc1C)C)O
Isomeric SMILES O=c1n(CCC)c2c(nc1c1ccc(C(=O)NCc3cnccc3)cc1)ccc(c2)NC(=O)CCCCCCCCCCC(=O)N[C@H](C(=O)N1C[C@@H](C[C@H]1C(=O)N[C@H](c1ccc(cc1)c1c(ncs1)C)C)O)C(C)(C)C
InChI InChI=1S/C59H73N9O7S/c1-7-31-67-48-32-45(28-29-47(48)65-52(57(67)74)42-22-26-44(27-23-42)55(72)61-35-40-17-16-30-60-34-40)64-50(70)18-14-12-10-8-9-11-13-15-19-51(71)66-54(59(4,5)6)58(75)68-36-46(69)33-49(68)56(73)63-38(2)41-20-24-43(25-21-41)53-39(3)62-37-76-53/h16-17,20-30,32,34,37-38,46,49,54,69H,7-15,18-19,31,33,35-36H2,1-6H3,(H,61,72)(H,63,73)(H,64,70)(H,66,71)/t38-,46+,49-,54+/m0/s1
InChI Key MLJZDBCOWWJHEE-LPLKMGJNSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups PROTACs, molecular glues and other degraders
Synonyms Click here for help
compound 5 [PMID: 36442664]
Database Links Click here for help
GtoPdb PubChem SID 473153859
PubChem CID 165437867
Search Google for chemical match using the InChIKey MLJZDBCOWWJHEE-LPLKMGJNSA-N
Search Google for chemicals with the same backbone MLJZDBCOWWJHEE
UniChem Compound Search for chemical match using the InChIKey MLJZDBCOWWJHEE-LPLKMGJNSA-N
UniChem Connectivity Search for chemical match using the InChIKey MLJZDBCOWWJHEE-LPLKMGJNSA-N