Dihydromethysticin

Details

• Internal ID: 6c0b3642-8b3e-4ad6-be54-d1c8f50c655a
• Taxonomy: Phenylpropanoids and polyketides > Kavalactones
• IUPAC Name: (2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
• SMILES (Canonical): COC1=CC(=O)OC(C1)CCC2=CC3=C(C=C2)OCO3
• SMILES (Isomeric): COC1=CC(=O)O[C@H](C1)CCC2=CC3=C(C=C2)OCO3
• InChI: InChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3/t11-/m0/s1
• InChI Key: RSIWXFIBHXYNFM-NSHDSACASA-N
• Popularity: 58 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28 g/mol
• Exact Mass: 276.09977361 g/mol
• Topological Polar Surface Area (TPSA): 54.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.19
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 19902-91-1
• (+)-Dihydromethysticin
• 7,8-Dihydromethysticin
• Methysticin, 7,8-dihydro-
• Dihydromethysticin (VAN)
• NSC 112159
• UNII-FZ66MQ73GS
• FZ66MQ73GS
• 2H-Pyran-2-one, 6-[2-(1,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-, (6S)-
• CCRIS 9368
• CHEBI:4573
• 2H-Pyran-2-one, 6-(2-(1,3-benzodioxol-5-yl)ethyl)-5,6-dihydro-4-methoxy-, (S)-
• NSC-112159
• (2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
• 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)phenethyl)-, (S)-
• Pseudomethysticin
• (6S)-6-[2-(1,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one
• (S)-6-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-4-methoxy-5,6-dihydro-2H-pyran-2-one
• |x-Methysticin
• (2S)-2-(2-(1,3-BENZODIOXOL-5-YL)ETHYL)-4-METHOXY-2,3-DIHYDROPYRAN-6-ONE
• 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-[3,4-(methylenedioxy)phenethyl]-, (S)-
• 2H-Pyran-2-one, 6-[2-(1,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-, (S)-
• Methysticin,8-dihydro-
• CHEMBL576066
• MEGxp0_001718
• SCHEMBL14524443
• ACon0_000957
• ACon1_001371
• DTXSID601314143
• HY-N0921
• MFCD00221731
• NSC112159
• CCG-208398
• CS-4245
• NCGC00180578-01
• AC-34189
• AS-79324
• (+)-Dihydromethysticin, analytical standard
• LS-127431
• FT-0700034
• (+)-Dihydromethysticin(+)-Dihydromethysticin
• C09926
• SR-05000002272
• J-018462
• Q-100244
• Q5276438
• SR-05000002272-2
• BRD-K87171303-001-01-2
• 2H-Pyran-2-one,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-, (S)-
• 2H-Pyran-2-one,6-dihydro-4-methoxy-6-[3,4-(methylenedioxy)phenethyl]-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9951	99.51%
Caco-2	+	0.9087	90.87%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8101	81.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9282	92.82%
OATP1B3 inhibitior	+	0.9609	96.09%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6628	66.28%
P-glycoprotein inhibitior	+	0.6854	68.54%
P-glycoprotein substrate	-	0.7303	73.03%
CYP3A4 substrate	+	0.5136	51.36%
CYP2C9 substrate	-	0.8087	80.87%
CYP2D6 substrate	-	0.8739	87.39%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	-	0.5441	54.41%
CYP2C19 inhibition	+	0.8327	83.27%
CYP2D6 inhibition	+	0.7461	74.61%
CYP1A2 inhibition	+	0.7754	77.54%
CYP2C8 inhibition	-	0.7083	70.83%
CYP inhibitory promiscuity	+	0.9153	91.53%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4891	48.91%
Eye corrosion	-	0.9678	96.78%
Eye irritation	+	0.6772	67.72%
Skin irritation	-	0.7747	77.47%
Skin corrosion	-	0.9566	95.66%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3591	35.91%
Micronuclear	-	0.6982	69.82%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.6602	66.02%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.7592	75.92%
Acute Oral Toxicity (c)	III	0.5123	51.23%
Estrogen receptor binding	+	0.7475	74.75%
Androgen receptor binding	+	0.6717	67.17%
Thyroid receptor binding	+	0.6821	68.21%
Glucocorticoid receptor binding	+	0.6371	63.71%
Aromatase binding	+	0.5303	53.03%
PPAR gamma	-	0.5231	52.31%
Honey bee toxicity	-	0.8129	81.29%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9382	93.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4481	P35228	Nitric oxide synthase, inducible	98.32%	94.80%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.58%	96.77%
CHEMBL2581	P07339	Cathepsin D	96.40%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.98%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.54%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.69%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.82%	85.14%
CHEMBL2039	P27338	Monoamine oxidase B	90.28%	92.51%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.19%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.89%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.77%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.71%	97.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.28%	93.40%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	87.68%	85.30%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.64%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.78%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.40%	96.09%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	83.34%	80.96%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.20%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.08%	99.17%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	82.32%	93.24%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.45%	96.00%
CHEMBL2535	P11166	Glucose transporter	80.44%	98.75%

Plants that contains it

• Aniba hostmanniana
• Piper methysticum

Cross-Links

• PubChem: 88308
• NPASS: NPC85830
• LOTUS: LTS0082007
• wikiData: Q5276438