cemdomespib   Click here for help

GtoPdb Ligand ID: 13726

Synonyms: BIIB-143 | BIIB143 | compound 13b [PMID: 22702513] | compound 3 [PMID: 35905686] | KU-596 | KU596 | RTA 901 | RTA-901
Compound class: Synthetic organic
Comment: Cemdomespib (BIIB143) is an orally bioavailable small molecule modulator of heat shock (molecular chaperone) proteins with neuroprotective activity [4,6]. It contains the same noviose sugar as the antibacterial compound and heat shock protein 90 (Hsp90) C-terminal inhibitor novobiocin, making it a member of the chemical class termed "novologues" or "noviomimetics" [1]. Hsp90 molecular chaperones are regarded as targets for cancer, neurodegenerative diseases and peripheral neuropathies [7]. Inhibition of Hsp90 by novologues increases expression of Hsp70 [2-3,5]. It is this latter mechanism that is proposed to be of therapeutic benefit in treating diabetic peripheral neuropathy.
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 7
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 97.25
Molecular weight 447.5
XLogP 1.05
No. Lipinski's rules broken 0

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(=O)NCCC1=CC=C(C=C1C2=CC(=CC=C2)F)O[C@H]3[C@@H]([C@@H]([C@H](C(C)(C)O3)OC)O)O
Isomeric SMILES CC(=O)NCCC1=C(C=C(C=C1)O[C@H]2[C@@H]([C@@H]([C@H](C(O2)(C)C)OC)O)O)C3=CC(=CC=C3)F
InChI InChI=1S/C24H30FNO6/c1-14(27)26-11-10-15-8-9-18(13-19(15)16-6-5-7-17(25)12-16)31-23-21(29)20(28)22(30-4)24(2,3)32-23/h5-9,12-13,20-23,28-29H,10-11H2,1-4H3,(H,26,27)/t20-,21+,22+,23+/m0/s1
InChI Key PDBWOHBMJQOBHL-WBADGQHESA-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
IUPAC Name Click here for help
N-[2-[4-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyloxan-2-yl]oxy-2-(3-fluorophenyl)phenyl]ethyl]acetamide
International Nonproprietary Names Click here for help
INN number INN
12042 cemdomespib
Synonyms Click here for help
BIIB-143 | BIIB143 | compound 13b [PMID: 22702513] | compound 3 [PMID: 35905686] | KU-596 | KU596 | RTA 901 | RTA-901
Database Links Click here for help
CAS Registry No. 1450642-92-8 (source: WHO INN record)
ChEMBL Ligand CHEMBL2159227
DrugBank Ligand DB18953
GtoPdb PubChem SID 507750360
PubChem CID 60148493
Search Google for chemical match using the InChIKey PDBWOHBMJQOBHL-WBADGQHESA-N
Search Google for chemicals with the same backbone PDBWOHBMJQOBHL
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UniChem Compound Search for chemical match using the InChIKey PDBWOHBMJQOBHL-WBADGQHESA-N
UniChem Connectivity Search for chemical match using the InChIKey PDBWOHBMJQOBHL-WBADGQHESA-N