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boditrectinib   Click here for help

GtoPdb Ligand ID: 12368

Synonyms: AUM-601 | AUM601 | CHC 2014 | CHC2014 | Chemical Compound 50 [US20160168156A1] [1] | HL 5101 | HL5101 | NOV 1601 | NOV-1601
Compound class: Synthetic organic
Comment: We mapped the structure for the INN boditrectinib via PubChem to research code AUM601, which is a selective, orally bioavailable pan-tropomyosin related kinase (TRK; a.k.a., neurotrophin tyrosine receptor kinase, NTRK) inhibitor [1]. It inhbits wild-type NTRKs and variants with resistance mutations. AUM601 is an oncology clinical lead that's being developed by AUM Biosciences. Previous research codes include CHC2014 and NOV1601.
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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Click here for structure editor
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 6
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 65.77
Molecular weight 438.2
XLogP 3.38
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 Fc1ccc(c(c1)[C@H]1CCCN1c1ccn2c(n1)c(/C=C/C(=O)N1CCNCC1)cn2)F
Isomeric SMILES C1C[C@@H](N(C1)c1nc2c(cnn2cc1)/C=C/C(=O)N1CCNCC1)c1c(ccc(c1)F)F
InChI InChI=1S/C23H24F2N6O/c24-17-4-5-19(25)18(14-17)20-2-1-10-30(20)21-7-11-31-23(28-21)16(15-27-31)3-6-22(32)29-12-8-26-9-13-29/h3-7,11,14-15,20,26H,1-2,8-10,12-13H2/b6-3+/t20-/m1/s1
InChI Key BQFYCHBYISNPFW-SQZHUTIHSA-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
(E)-3-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-1-piperazin-1-ylprop-2-en-1-one
International Nonproprietary Names Click here for help
INN number INN
12591 boditrectinib
Synonyms Click here for help
AUM-601 | AUM601 | CHC 2014 | CHC2014 | Chemical Compound 50 [US20160168156A1] [1] | HL 5101 | HL5101 | NOV 1601 | NOV-1601
Database Links Click here for help
CAS Registry No. 1940165-80-9 (source: WHO INN record)
GtoPdb PubChem SID 479821159
PubChem CID 121395201
Search Google for chemical match using the InChIKey BQFYCHBYISNPFW-SQZHUTIHSA-N
Search Google for chemicals with the same backbone BQFYCHBYISNPFW
Search PubMed clinical trials boditrectinib
Search PubMed titles boditrectinib
Search PubMed titles/abstracts boditrectinib
UniChem Compound Search for chemical match using the InChIKey BQFYCHBYISNPFW-SQZHUTIHSA-N
UniChem Connectivity Search for chemical match using the InChIKey BQFYCHBYISNPFW-SQZHUTIHSA-N