(2S,3S,3aS)-5-methoxy-3-methyl-2-phenyl-3a-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one

Details

• Internal ID: 5e0de516-500e-4a55-8f63-febf69f207d1
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3S,3aS)-5-methoxy-3-methyl-2-phenyl-3a-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
• SMILES (Canonical): CC1C(OC2=CC(=O)C(=CC12CC=C)OC)C3=CC=CC=C3
• SMILES (Isomeric): C[C@@H]1[C@H](OC2=CC(=O)C(=C[C@]12CC=C)OC)C3=CC=CC=C3
• InChI: InChI=1S/C19H20O3/c1-4-10-19-12-16(21-3)15(20)11-17(19)22-18(13(19)2)14-8-6-5-7-9-14/h4-9,11-13,18H,1,10H2,2-3H3/t13-,18+,19-/m1/s1
• InChI Key: BZGONHLQLISSBB-ZNZDAUKMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₃
• Molecular Weight: 296.40 g/mol
• Exact Mass: 296.14124450 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.95
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8183	81.83%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6113	61.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8956	89.56%
OATP1B3 inhibitior	+	0.9034	90.34%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6826	68.26%
P-glycoprotein inhibitior	-	0.6568	65.68%
P-glycoprotein substrate	-	0.7566	75.66%
CYP3A4 substrate	+	0.5263	52.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8375	83.75%
CYP3A4 inhibition	+	0.6468	64.68%
CYP2C9 inhibition	-	0.6448	64.48%
CYP2C19 inhibition	+	0.6459	64.59%
CYP2D6 inhibition	-	0.8876	88.76%
CYP1A2 inhibition	+	0.5246	52.46%
CYP2C8 inhibition	+	0.5405	54.05%
CYP inhibitory promiscuity	+	0.9099	90.99%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4391	43.91%
Eye corrosion	-	0.9655	96.55%
Eye irritation	-	0.9286	92.86%
Skin irritation	-	0.7006	70.06%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7889	78.89%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	+	0.6427	64.27%
skin sensitisation	-	0.6170	61.70%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.6704	67.04%
Acute Oral Toxicity (c)	III	0.5339	53.39%
Estrogen receptor binding	+	0.7910	79.10%
Androgen receptor binding	+	0.5695	56.95%
Thyroid receptor binding	-	0.6028	60.28%
Glucocorticoid receptor binding	-	0.5088	50.88%
Aromatase binding	+	0.6872	68.72%
PPAR gamma	-	0.5149	51.49%
Honey bee toxicity	-	0.7173	71.73%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9868	98.68%

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	97.39%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.85%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.58%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.74%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	91.20%	91.49%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.38%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.08%	97.09%
CHEMBL2581	P07339	Cathepsin D	84.58%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.73%	96.00%
CHEMBL1907	P15144	Aminopeptidase N	80.32%	93.31%

Plants that contains it

• Rhodostemonodaphne miranda

Cross-Links

• PubChem: 162820448
• LOTUS: LTS0104798
• wikiData: Q104950453