Methysticin

Details

• Internal ID: ee352678-6786-4053-ab22-5ea0f8bb5612
• Taxonomy: Phenylpropanoids and polyketides > Kavalactones
• IUPAC Name: (2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one
• SMILES (Canonical): COC1=CC(=O)OC(C1)C=CC2=CC3=C(C=C2)OCO3
• SMILES (Isomeric): COC1=CC(=O)O[C@H](C1)/C=C/C2=CC3=C(C=C2)OCO3
• InChI: InChI=1S/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m0/s1
• InChI Key: GTEXBOVBADJOQH-FWEMWIAWSA-N
• Popularity: 42 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27 g/mol
• Exact Mass: 274.08412354 g/mol
• Topological Polar Surface Area (TPSA): 54.00 Ų
• XlogP: 2.40

Synonyms

• Kavatin
• 495-85-2
• Kavahin
• (+)-Methysticin
• Methylsticin
• NSC 112158
• UNII-M832AIJ6HX
• M832AIJ6HX
• BRN 0091701
• CCRIS 9370
• DTXSID5033674
• NSC-112158
• (R)-5,6-Dihydro-4-methoxy-6-(3,4-(methylenedioxy)styryl)-2H-pyran-2-one
• (2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one
• (R-(E))-6-(2-(1,3-Benzodioxol-5-yl)ethenyl)-5,6-dihydro-4-methoxy-2H-pyran-2-one
• CHEBI:6895
• DTXCID3013674
• 5-19-10-00456 (Beilstein Handbook Reference)
• 4-Methoxy-6-(beta-(3',4'-methylenedioxyphenyl)vinyl)-5,6-dihydro-alpha-pyrone
• (R,E)-6-(2-(benzo[d][1,3]dioxol-5-yl)vinyl)-4-methoxy-5,6-dihydro-2H-pyran-2-one
• 5-Hydroxy-3-methoxy-7-(3,4-(methylenedioxy)phenyl)-2,6-heptadienoic acid gamma-lactone
• 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)styryl)-, (R)-
• 2H-Pyran-2-one, 6-(2-(1,3-benzodioxol-5-yl)ethenyl)-5,6-dihydro-4-methoxy-, (R-(E))-
• 2H-Pyran-2-one,6-[(1E)-2-(1,3-benzodioxol-5-yl)ethenyl]-5,6-dihydro-4-methoxy-, (6R)-
• 6-(3',4'-METHYLENEDIOXYSTYRYL)-4-METHOXY-5,6-DIHYDRO-2H-PYRAN-2-ONE
• (6R)-6-[(1E)-2-(1,3-Benzodioxol-5-yl)ethenyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one
• 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)styryl)-, (R)- (VAN)
• (6R)-6-((1E)-2-(1,3-BENZODIOXOL-5-YL)ETHENYL)-5,6-DIHYDRO-4-METHOXY-2H-PYRAN-2-ONE
• R-(+)-Methysticin
• METHYSTICIN [MI]
• CHEMBL579224
• SCHEMBL1393508
• Tox21_200901
• NSC112158
• AKOS030573530
• Ethyl 2-(isobutoxycarbonylamino)acetate
• R-(+)-Methysticin, analytical standard
• NCGC00091903-01
• NCGC00091903-02
• NCGC00258455-01
• AC-34499
• CAS-495-85-2
• LS-127432
• C09952
• A827756
• Q3333720
• (2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)vinyl]-4-methoxy-2,3-dihydropyran-6-one
• (6R)-6-(2-Benzo[1,3]Dioxol-5-ylethenyl)-4-Methoxy-5,6-Dihydropyran-2-one
• (6R)-6-[(E)-2-(1,3-benzodioxol-5-yl)vinyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
• 2H-Pyran-2-one,3-benzodioxol-5-yl)ethenyl]-5,6-dihydro-4-methoxy-, [R-(E)]-
• 2H-Pyran-2-one,6-dihydro-4-methoxy-6-[3,4-(methylenedioxy)styryl]-, (+)-
• 2H-Pyran-2-one,6-dihydro-4-methoxy-6-[3,4-(methylenedioxy)styryl]-, (R)-
• 5-hydroxy-3-methoxy-7-[3,4-(methylenedioxy)phenyl]-2,6-heptadienoic acid delta-lactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	12589.3 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	2511.9 nM; 2511.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	5011.9 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.01%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	97.74%	94.80%
CHEMBL2039	P27338	Monoamine oxidase B	97.61%	92.51%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	95.54%	85.30%
CHEMBL1951	P21397	Monoamine oxidase A	95.08%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.87%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.81%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.51%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.52%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.49%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.55%	94.45%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	90.03%	80.96%
CHEMBL2581	P07339	Cathepsin D	88.71%	98.95%
CHEMBL240	Q12809	HERG	87.75%	89.76%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.37%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.71%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.29%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.17%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.44%	92.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.93%	93.40%

Plants that contains it

• Piper methysticum

Cross-Links

• PubChem: 5281567
• NPASS: NPC193484
• ChEMBL: CHEMBL579224
• LOTUS: LTS0124512
• wikiData: Q3333720