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AR-67   Click here for help

GtoPdb Ligand ID: 8919

Synonyms: AR67 | compound 14 [PMID:11052802] | DB-67 | DB67 | silatecan
Compound class: Synthetic organic
Comment: AR-67 is a synthetic, highly lipophilic derivative of the natural alkaloid camptothecin (PubChem CID 24360), with potential antineoplastic [3,5] and radiosensitizing activities [4]. The compound has improved physicochemical properties compared to other camptothecin-derived drugs (e.g. SN-38, the active metabolite of the anti-cancer drug irinotecan, and topotecan) [2].
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 5
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 101.65
Molecular weight 478.19
XLogP 5.09
No. Lipinski's rules broken 1

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 CCC1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)[Si](C(C)(C)C)(C)C)O
Isomeric SMILES CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)[Si](C(C)(C)C)(C)C)O
InChI InChI=1S/C26H30N2O5Si/c1-7-26(32)18-11-20-21-16(12-28(20)23(30)17(18)13-33-24(26)31)22(34(5,6)25(2,3)4)15-10-14(29)8-9-19(15)27-21/h8-11,29,32H,7,12-13H2,1-6H3/t26-/m0/s1
InChI Key XUSKJHCMMWAAHV-SANMLTNESA-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
Synonyms Click here for help
AR67 | compound 14 [PMID:11052802] | DB-67 | DB67 | silatecan
Database Links Click here for help
CAS Registry No. 220913-32-6
ChEMBL Ligand CHEMBL412309
GtoPdb PubChem SID 310264700
PubChem CID 6712744
Search Google for chemical match using the InChIKey XUSKJHCMMWAAHV-SANMLTNESA-N
Search Google for chemicals with the same backbone XUSKJHCMMWAAHV
UniChem Compound Search for chemical match using the InChIKey XUSKJHCMMWAAHV-SANMLTNESA-N
UniChem Connectivity Search for chemical match using the InChIKey XUSKJHCMMWAAHV-SANMLTNESA-N