Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Kava
- DrugBank Accession Number
- DB01322
- Background
Not Available
- Type
- Small Molecule
- Groups
- Approved, Investigational, Nutraceutical
- Structure
Structure for Kava (DB01322)
- Weight
- Average: 232.275
Monoisotopic: 232.109944378 - Chemical Formula
- C14H16O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dihydropyranones. These are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyrans
- Sub Class
- Pyranones and derivatives
- Direct Parent
- Dihydropyranones
- Alternative Parents
- Vinylogous esters / Enoate esters / Lactones / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic heteromonocyclic compound / Alpha,beta-unsaturated carboxylic ester / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dihydropyranone / Enoate ester / Hydrocarbon derivative / Lactone / Monocarboxylic acid or derivatives
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- BOW48C81XP
- CAS number
- 9000-38-8
- InChI Key
- OMNGEVNATYFZGG-BQYQJAHWSA-N
- InChI
- InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h3,5-8,10,12H,2,4,9H2,1H3/b8-7+
- IUPAC Name
- 6-[(1E)-2-(cyclohexa-1,5-dien-1-yl)ethenyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
- SMILES
- COC1=CC(=O)OC(C1)\C=C\C1=CCCC=C1
References
- Synthesis Reference
Klaus-Peter Schwabe, "Kava-kava extract, process for the production thereof and use thereof." U.S. Patent US5296224, issued November, 1963.
US5296224- General References
- Uebelhack R, Franke L, Schewe HJ: Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava). Pharmacopsychiatry. 1998 Sep;31(5):187-92. [Article]
- Baum SS, Hill R, Rommelspacher H: Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats. Prog Neuropsychopharmacol Biol Psychiatry. 1998 Oct;22(7):1105-20. [Article]
- Seitz U, Schule A, Gleitz J: [3H]-monoamine uptake inhibition properties of kava pyrones. Planta Med. 1997 Dec;63(6):548-9. [Article]
- Lim ST, Dragull K, Tang CS, Bittenbender HC, Efird JT, Nerurkar PV: Effects of kava alkaloid, pipermethystine, and kavalactones on oxidative stress and cytochrome P450 in F-344 rats. Toxicol Sci. 2007 May;97(1):214-21. Epub 2007 Feb 27. [Article]
- Sorrentino L, Capasso A, Schmidt M: Safety of ethanolic kava extract: Results of a study of chronic toxicity in rats. Phytomedicine. 2006 Sep;13(8):542-9. Epub 2006 Aug 14. [Article]
- External Links
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Completed Treatment Healthy Volunteers (HV) 1 somestatus stop reason just information to hide 2 Completed Treatment Anxiety Disorders / Major Depressive Disorder (MDD) 1 somestatus stop reason just information to hide 2 Completed Treatment Pharmacokinetics 1 somestatus stop reason just information to hide 2 Recruiting Prevention Smoking 2 somestatus stop reason just information to hide 2 Terminated Treatment Anxiety Disorders 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0632 mg/mL ALOGPS logP 2.74 ALOGPS logP 2.05 Chemaxon logS -3.6 ALOGPS pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 35.53 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 70.38 m3·mol-1 Chemaxon Polarizability 25.68 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9835 Blood Brain Barrier + 0.7757 Caco-2 permeable + 0.7784 P-glycoprotein substrate Substrate 0.5295 P-glycoprotein inhibitor I Inhibitor 0.7529 P-glycoprotein inhibitor II Non-inhibitor 0.8643 Renal organic cation transporter Non-inhibitor 0.6815 CYP450 2C9 substrate Non-substrate 0.7903 CYP450 2D6 substrate Non-substrate 0.8869 CYP450 3A4 substrate Non-substrate 0.5386 CYP450 1A2 substrate Inhibitor 0.6492 CYP450 2C9 inhibitor Non-inhibitor 0.9142 CYP450 2D6 inhibitor Non-inhibitor 0.924 CYP450 2C19 inhibitor Inhibitor 0.6734 CYP450 3A4 inhibitor Non-inhibitor 0.8919 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5086 Ames test Non AMES toxic 0.7569 Carcinogenicity Non-carcinogens 0.9371 Biodegradation Ready biodegradable 0.7719 Rat acute toxicity 1.8786 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8457 hERG inhibition (predictor II) Non-inhibitor 0.9466
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0950000000-3f8a7eebc80b33cd9301 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0900000000-e7b59a797a95fa6a44aa Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0900000000-22fbf6926e257eba9b82 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-3910000000-948eb284d19250268281 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a6r-7900000000-f47baeea95ece075c3aa Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00mo-9510000000-ace4ee9abcf2917760a4 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 156.03647 predictedDeepCCS 1.0 (2019) [M+H]+ 158.43202 predictedDeepCCS 1.0 (2019) [M+Na]+ 164.45416 predictedDeepCCS 1.0 (2019)
Drug created at June 30, 2007 17:19 / Updated at February 13, 2021 10:50