5-[(3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]-1,3-benzodioxole

Details

• Internal ID: 6ffe805e-9a6e-4513-bb1b-70961ba3fc6b
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-[(3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]-1,3-benzodioxole
• SMILES (Canonical): CC=CC1=CC2=C(C(=C1)OC)OC(C2C)C3=CC4=C(C=C3)OCO4
• SMILES (Isomeric): C/C=C/C1=CC2=C(C(=C1)OC)OC([C@H]2C)C3=CC4=C(C=C3)OCO4
• InChI: InChI=1S/C20H20O4/c1-4-5-13-8-15-12(2)19(24-20(15)18(9-13)21-3)14-6-7-16-17(10-14)23-11-22-16/h4-10,12,19H,11H2,1-3H3/b5-4+/t12-,19?/m0/s1
• InChI Key: DMMQXURQRMNSBM-SWDBHPRBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.40 g/mol
• Exact Mass: 324.13615911 g/mol
• Topological Polar Surface Area (TPSA): 36.90 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.69
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• (-)-Licarin-B
• NSC370990
• NSC-370990

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	+	0.9016	90.16%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6981	69.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8886	88.86%
OATP1B3 inhibitior	+	0.9540	95.40%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8794	87.94%
P-glycoprotein inhibitior	+	0.7723	77.23%
P-glycoprotein substrate	-	0.8122	81.22%
CYP3A4 substrate	+	0.5544	55.44%
CYP2C9 substrate	+	0.5714	57.14%
CYP2D6 substrate	-	0.7449	74.49%
CYP3A4 inhibition	+	0.9301	93.01%
CYP2C9 inhibition	+	0.9050	90.50%
CYP2C19 inhibition	+	0.9277	92.77%
CYP2D6 inhibition	+	0.6621	66.21%
CYP1A2 inhibition	+	0.5974	59.74%
CYP2C8 inhibition	+	0.4582	45.82%
CYP inhibitory promiscuity	+	0.9771	97.71%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9408	94.08%
Carcinogenicity (trinary)	Danger	0.4094	40.94%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9290	92.90%
Skin irritation	-	0.7840	78.40%
Skin corrosion	-	0.9686	96.86%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8349	83.49%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.6989	69.89%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.5802	58.02%
Acute Oral Toxicity (c)	III	0.6080	60.80%
Estrogen receptor binding	+	0.8023	80.23%
Androgen receptor binding	+	0.5841	58.41%
Thyroid receptor binding	+	0.7395	73.95%
Glucocorticoid receptor binding	+	0.7816	78.16%
Aromatase binding	+	0.5460	54.60%
PPAR gamma	-	0.5092	50.92%
Honey bee toxicity	-	0.7505	75.05%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.9863	98.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.31%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.15%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.63%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.05%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.79%	96.09%
CHEMBL240	Q12809	HERG	92.57%	89.76%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.05%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.98%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.16%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.96%	89.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	88.45%	82.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.64%	97.14%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.66%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.47%	92.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.17%	89.62%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	82.96%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	82.43%	94.73%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	82.31%	97.31%
CHEMBL3438	Q05513	Protein kinase C zeta	82.31%	88.48%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.52%	96.77%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	81.05%	96.86%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.62%	95.89%
CHEMBL2535	P11166	Glucose transporter	80.36%	98.75%

Plants that contains it

• Aristolochia taliscana
• Machilus obovatifolia
• Machilus thunbergii
• Magnolia denudata
• Myristica fragrans
• Ocotea porosa
• Saururus chinensis
• Staudtia kamerunensis

Cross-Links

• PubChem: 5384942
• NPASS: NPC155338
• LOTUS: LTS0249202
• wikiData: Q104985199