Kavain

Details

• Internal ID: 71b1662f-440e-4490-b19b-19d77f82e356
• Taxonomy: Phenylpropanoids and polyketides > Kavalactones
• IUPAC Name: (2R)-4-methoxy-2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one
• SMILES (Canonical): COC1=CC(=O)OC(C1)C=CC2=CC=CC=C2
• SMILES (Isomeric): COC1=CC(=O)O[C@H](C1)/C=C/C2=CC=CC=C2
• InChI: InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+/t12-/m0/s1
• InChI Key: XEAQIWGXBXCYFX-GUOLPTJISA-N
• Popularity: 121 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₃
• Molecular Weight: 230.26 g/mol
• Exact Mass: 230.094294304 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.55
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• Kawain
• (+)-Kavain
• 500-64-1
• Gonosan
• L-KAWAIN
• Kawaih
• D-Kawain
• DTXSID5033595
• W1ES06373M
• Kavain, dl-
• NSC 112162
• NSC-112162
• (+)-KAWAIN
• UNII-W1ES06373M
• (R)-(+)-Kavain
• CHEBI:6117
• 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-styryl-, (+)-
• DTXCID3013595
• EINECS 207-907-2
• (R)-5,6-Dihydro-4-methoxy-6-styryl-2H-pyran-2-one
• (R,E)-4-methoxy-6-styryl-5,6-dihydro-2H-pyran-2-one
• KAWAIN (USP-RS)
• KAWAIN [USP-RS]
• kavaine
• 4-Methoxy-6-(beta-phenylvinyl)-5,6-dihydro-alpha-pyrone
• 5-Hydroxy-3-methoxy-7-phenyl-2,6-heptadienoic acid gamma-lactone
• 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethenyl)-, (R-(E))-
• 2H-PYRAN-2-ONE, 5,6-DIHYDRO-4-METHOXY-6-((1E)-2-PHENYLETHENYL)-, (6R)-
• (R-(E))-5,6-Dihydro-4-methoxy-6-styryl-2H-pyran-2-one
• [R-(E)]-5,6-dihydro-4-methoxy-6-styryl-2H-pyran-2-one
• 2H-PYRAN-2-ONE, 5,6-DIHYDRO-4-METHOXY-6-STYRYL-, (R)-
• 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethenyl)-, [R-(E)]-
• Kavaform (TN)
• CAS-500-64-1
• KAWAIN [WHO-DD]
• Prestwick2_000207
• Prestwick3_000207
• KAWAIN [MI]
• BSPBio_000193
• MLS002154236
• SCHEMBL515202
• BPBio1_000213
• CHEMBL578607
• CHEBI:92164
• XEAQIWGXBXCYFX-GUOLPTJISA-N
• HMS1568J15
• HMS2095J15
• HMS2230N15
• HMS3887G03
• HY-B1671
• Tox21_200907
• NSC112162
• s9409
• CCG-266792
• NCGC00091905-01
• NCGC00091905-02
• NCGC00091905-03
• NCGC00091905-05
• NCGC00258461-01
• AC-35093
• MS-23309
• SMR001233508
• AB00513818
• CS-0013634
• C09947
• D08096
• Q-100559
• Q3194310
• BRD-K09497549-001-03-6
• 2H-Pyran-2-one,6-dihydro-4-methoxy-6-styryl-, (+)-
• 2H-Pyran-2-one,6-dihydro-4-methoxy-6-styryl-, (R)-
• (2R)-4-methoxy-2-[(E)-styryl]-2,3-dihydropyran-6-one
• 5-hydroxy-3-methoxy-7-phenyl-2,6-heptadienoic acid delta-lactone
• (6R)-4-methoxy-6-[(E)-2-phenylvinyl]-5,6-dihydro-2H-pyran-2-one
• (6R)-5,6-Dihydro-4-methoxy-6-[(1E)-2-phenylethenyl]-2H-pyran-2-one
• 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethenyl)-,[R-(E)]-
• 2H-Pyran-2-one,6-dihydro-4-methoxy-6-(2-phenylethenyl)-, [R-(E)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9958	99.58%
Caco-2	+	0.9330	93.30%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7139	71.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9120	91.20%
OATP1B3 inhibitior	+	0.9778	97.78%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5764	57.64%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.9166	91.66%
CYP3A4 substrate	-	0.5309	53.09%
CYP2C9 substrate	-	0.8036	80.36%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.9104	91.04%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.7145	71.45%
CYP inhibitory promiscuity	+	0.6336	63.36%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7958	79.58%
Carcinogenicity (trinary)	Non-required	0.5366	53.66%
Eye corrosion	-	0.7857	78.57%
Eye irritation	+	0.5643	56.43%
Skin irritation	+	0.5351	53.51%
Skin corrosion	-	0.9751	97.51%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3831	38.31%
Micronuclear	-	0.5356	53.56%
Hepatotoxicity	+	0.9783	97.83%
skin sensitisation	-	0.7483	74.83%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.8000	80.00%
Nephrotoxicity	+	0.5143	51.43%
Acute Oral Toxicity (c)	III	0.5217	52.17%
Estrogen receptor binding	+	0.6280	62.80%
Androgen receptor binding	+	0.8659	86.59%
Thyroid receptor binding	-	0.8319	83.19%
Glucocorticoid receptor binding	-	0.7787	77.87%
Aromatase binding	+	0.6667	66.67%
PPAR gamma	-	0.7120	71.20%
Honey bee toxicity	-	0.8472	84.72%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.7300	73.00%
Fish aquatic toxicity	+	0.7989	79.89%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	12589.3 nM	Potency	PMID: 7807120

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.72%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.52%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.64%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.16%	96.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.18%	93.99%
CHEMBL2581	P07339	Cathepsin D	88.04%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.49%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.31%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	82.46%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.93%	97.09%

Plants that contains it

• Piper methysticum

Cross-Links

• PubChem: 5281565
• NPASS: NPC286608
• ChEMBL: CHEMBL578607
• LOTUS: LTS0061603
• wikiData: Q3194310