SN-38   Click here for help

GtoPdb Ligand ID: 6925

Synonyms: SN 38 lactone | SN38
PDB Ligand
Compound class: Synthetic organic
Comment: Active metabolite of the topoisomerase inhibitor irinotecan.
A bioRxiv preprint reports on a machine learning approach that was used to identify SN-38 for potential anti-tumour activity in glioblastoma multiforme (GBM) stem cell lines, with nanomolar potencies [1].

SN-38 is commercially available from our sponsors

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 2
Topological polar surface area 101.65
Molecular weight 392.14
XLogP 3.4
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 CCC1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)O
Isomeric SMILES CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)O
InChI InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1
InChI Key FJHBVJOVLFPMQE-QFIPXVFZSA-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
Prodrug irinotecan
IUPAC Name Click here for help
(19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
Synonyms Click here for help
SN 38 lactone | SN38
Database Links Click here for help
ChEMBL Ligand CHEMBL837
GtoPdb PubChem SID 178103507
PubChem CID 104842
RCSB PDB Ligand RS4
Search Google for chemical match using the InChIKey FJHBVJOVLFPMQE-QFIPXVFZSA-N
Search Google for chemicals with the same backbone FJHBVJOVLFPMQE
UniChem Compound Search for chemical match using the InChIKey FJHBVJOVLFPMQE-QFIPXVFZSA-N
UniChem Connectivity Search for chemical match using the InChIKey FJHBVJOVLFPMQE-QFIPXVFZSA-N
Wikipedia SN-38

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MedChemExpress
SN-38 (links to external site)
Cat. No. HY-13704