NAV

Kava

Identification

Generic Name
Kava
DrugBank Accession Number
DB01322
Background

Not Available

Type
Small Molecule
Groups
Approved, Investigational, Nutraceutical
Structure
3D
Similar Structures
Weight
Average: 232.275
Monoisotopic: 232.109944378
Chemical Formula
C14H16O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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
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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
  1. 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]
  2. 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]
  3. Seitz U, Schule A, Gleitz J: [3H]-monoamine uptake inhibition properties of kava pyrones. Planta Med. 1997 Dec;63(6):548-9. [Article]
  4. 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]
  5. 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]
KEGG Compound
C07611
PubChem Compound
5281052
PubChem Substance
46505711
ChemSpider
4444512
RxNav
285228
Drugs.com
Drugs.com Drug Page
Wikipedia
Kava

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentHealthy Volunteers (HV)1
2CompletedTreatmentAnxiety Disorders / Major Depressive Disorder (MDD)1
2CompletedTreatmentPharmacokinetics1
2Not Yet RecruitingPreventionSmoking1
2RecruitingPreventionSmoking1

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
PropertyValueSource
Water Solubility0.0632 mg/mLALOGPS
logP2.74ALOGPS
logP2.05Chemaxon
logS-3.6ALOGPS
pKa (Strongest Basic)-4.8Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area35.53 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity70.38 m3·mol-1Chemaxon
Polarizability25.68 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9835
Blood Brain Barrier+0.7757
Caco-2 permeable+0.7784
P-glycoprotein substrateSubstrate0.5295
P-glycoprotein inhibitor IInhibitor0.7529
P-glycoprotein inhibitor IINon-inhibitor0.8643
Renal organic cation transporterNon-inhibitor0.6815
CYP450 2C9 substrateNon-substrate0.7903
CYP450 2D6 substrateNon-substrate0.8869
CYP450 3A4 substrateNon-substrate0.5386
CYP450 1A2 substrateInhibitor0.6492
CYP450 2C9 inhibitorNon-inhibitor0.9142
CYP450 2D6 inhibitorNon-inhibitor0.924
CYP450 2C19 inhibitorInhibitor0.6734
CYP450 3A4 inhibitorNon-inhibitor0.8919
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5086
Ames testNon AMES toxic0.7569
CarcinogenicityNon-carcinogens0.9371
BiodegradationReady biodegradable0.7719
Rat acute toxicity1.8786 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8457
hERG inhibition (predictor II)Non-inhibitor0.9466
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0950000000-3f8a7eebc80b33cd9301
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-e7b59a797a95fa6a44aa
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-22fbf6926e257eba9b82
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-3910000000-948eb284d19250268281
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6r-7900000000-f47baeea95ece075c3aa
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00mo-9510000000-ace4ee9abcf2917760a4
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-156.03647
predicted
DeepCCS 1.0 (2019)
[M+H]+158.43202
predicted
DeepCCS 1.0 (2019)
[M+Na]+164.45416
predicted
DeepCCS 1.0 (2019)

Drug created at June 30, 2007 17:19 / Updated at February 13, 2021 10:50