CHEBI:78316 - (S)-(−)-verbenone

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ChEBI Name (S)-(−)-verbenone
ChEBI ID CHEBI:78316
ChEBI ASCII Name (S)-(-)-verbenone
Definition A 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one in which both chiral centres have S configuration.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C10H14O
Net Charge 0
Average Mass 150.21760
Monoisotopic Mass 150.10447
InChI InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m0/s1
InChIKey DCSCXTJOXBUFGB-JGVFFNPUSA-N
SMILES CC1=CC(=O)[C@H]2C[C@@H]1C2(C)C
Roles Classification
Application(s): expectorant
Compounds that are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing. Compare with mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration, and antitussives, which suppress the cough reflex.
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ChEBI Ontology
Outgoing (S)-(−)-verbenone (CHEBI:78316) has role expectorant (CHEBI:77035)
(S)-(−)-verbenone (CHEBI:78316) is a 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one (CHEBI:78315)
(S)-(−)-verbenone (CHEBI:78316) is enantiomer of (R)-(+)-verbenone (CHEBI:9955)
Incoming (R)-(+)-verbenone (CHEBI:9955) is enantiomer of (S)-(−)-verbenone (CHEBI:78316)
IUPAC Name
(1S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
Synonyms Sources
(−)-cis-verbenone NIST Chemistry WebBook
(−)-verbenone ChemIDplus
l-verbenoe ChemIDplus
levoverbenone ChEBI
Manual Xrefs Databases
4587 DrugCentral
Levoverbenone Wikipedia
View more database links
Registry Numbers Types Sources
1196-01-6 CAS Registry Number ChemIDplus
1196-01-6 CAS Registry Number NIST Chemistry WebBook
1907623 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
24339334 PubMed citation Europe PMC
Last Modified
22 February 2017