α-humulene   Click here for help

GtoPdb Ligand ID: 13236

Synonyms: alpha-caryophyllene | alpha-Humulene | humulene
PDB Ligand
Compound class: Natural product
Comment: α-humulene is a terpene phytochemical. It enhances the agonist activity of the cannabinoid agonist WIN55212-2 at CB receptors [1].

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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 0
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 0
Molecular weight 204.35
XLogP 5.94
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/1=C\CC/C(=C/CC(C)(C)/C=C/C1)/C
Isomeric SMILES C/C/1=C\CC(/C=C/C/C(=C/CC1)/C)(C)C
InChI InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6+,13-7+,14-10+
InChI Key FAMPSKZZVDUYOS-HRGUGZIWSA-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 Natural product
IUPAC Name Click here for help
(1E,4E,8E)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene
Synonyms Click here for help
alpha-caryophyllene | alpha-Humulene | humulene
Database Links Click here for help
ChEMBL Ligand CHEMBL251280
GtoPdb PubChem SID 491300018
LIPID MAPS LMPR0103110001
PubChem CID 5281520
RCSB PDB Ligand V8Z
Search Google for chemical match using the InChIKey FAMPSKZZVDUYOS-HRGUGZIWSA-N
Search Google for chemicals with the same backbone FAMPSKZZVDUYOS
UniChem Compound Search for chemical match using the InChIKey FAMPSKZZVDUYOS-HRGUGZIWSA-N
UniChem Connectivity Search for chemical match using the InChIKey FAMPSKZZVDUYOS-HRGUGZIWSA-N

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MedChemExpress
α-Humulene (links to external site)
Cat. No. HY-N6968