solanidine   Click here for help

GtoPdb Ligand ID: 12500

Compound class: Natural product
Comment: Solanidine is a plant-derived steroidal alkaloid compound, that is present in the Solanaceae (potato) family, Fritillaria species, and Veratrum grandiflorum [2]. Its metabolism is being investigated as a method of predicting an individual's CYP2D6 activity [1,3-4].

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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 2
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 23.47
Molecular weight 397.64
XLogP 6.14
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 C[C@H]1CC[C@@H]2[C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5CC[C@@]43C)O)N2C1
Isomeric SMILES C[C@H]1CC[C@@H]2[C@H]([C@H]3[C@@H](N2C1)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O)C)C)C
InChI InChI=1S/C27H43NO/c1-16-5-8-23-17(2)25-24(28(23)15-16)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-25,29H,5,7-15H2,1-4H3/t16-,17+,19-,20+,21-,22-,23+,24-,25-,26-,27-/m0/s1
InChI Key JVKYZPBMZPJNAJ-OQFNDJACSA-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/)
References
1. Behrle AC, Douglas J, Leeder JS, van Haandel L. (2022)
Isolation and Identification of 3,4-Seco-Solanidine-3,4-dioic acid (SSDA) as a Urinary Biomarker of Cytochrome P450 2D6 (CYP2D6) Activity.
Drug Metab Dispos, 50 (10): 1342-51. [PMID:35878926]
2. Gao L, Chen F, Li X, Xu S, Huang W, Ye Y. (2016)
Three new alkaloids from Veratrum grandiflorum Loes with inhibition activities on Hedgehog pathway.
Bioorg Med Chem Lett, 26 (19): 4735-4738. [PMID:27567371]
3. Magliocco G, Desmeules J, Matthey A, Quirós-Guerrero LM, Bararpour N, Joye T, Marcourt L, Queiroz EF, Wolfender JL, Gloor Y et al.. (2021)
Metabolomics reveals biomarkers in human urine and plasma to predict cytochrome P450 2D6 (CYP2D6) activity.
Br J Pharmacol, 178 (23): 4708-4725. [PMID:34363609]
4. Wollmann BM, Størset E, Kringen MK, Molden E, Smith RL. (2023)
Prediction of CYP2D6 poor metabolizers by measurements of solanidine and metabolites-a study in 839 patients with known CYP2D6 genotype.
Eur J Clin Pharmacol, 79 (4): 523-531. [PMID:36806969]