Sesibiricin

Details

• Internal ID: 2749dbc1-1e6c-4be4-aa43-1381d3241544
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 7-methoxy-5-(3-methylbut-2-enoxy)-8-(3-methylbut-2-enyl)chromen-2-one
• SMILES (Canonical): CC(=CCC1=C(C=C(C2=C1OC(=O)C=C2)OCC=C(C)C)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C=C(C2=C1OC(=O)C=C2)OCC=C(C)C)OC)C
• InChI: InChI=1S/C20H24O4/c1-13(2)6-7-15-17(22-5)12-18(23-11-10-14(3)4)16-8-9-19(21)24-20(15)16/h6,8-10,12H,7,11H2,1-5H3
• InChI Key: CHXXLEUCXDMIPM-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.16745924 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.66
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 26481-11-8
• 7-Methoxy-8-(3-methyl-2-butenyl)-5-[(3-methyl-2-butenyl)oxy]-2H-1-benzopyran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.8259	82.59%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7302	73.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9073	90.73%
OATP1B3 inhibitior	+	0.9370	93.70%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8975	89.75%
P-glycoprotein inhibitior	+	0.7411	74.11%
P-glycoprotein substrate	-	0.7472	74.72%
CYP3A4 substrate	-	0.5189	51.89%
CYP2C9 substrate	-	0.6607	66.07%
CYP2D6 substrate	-	0.8073	80.73%
CYP3A4 inhibition	-	0.7056	70.56%
CYP2C9 inhibition	+	0.7235	72.35%
CYP2C19 inhibition	+	0.9426	94.26%
CYP2D6 inhibition	-	0.7074	70.74%
CYP1A2 inhibition	+	0.9692	96.92%
CYP2C8 inhibition	-	0.5740	57.40%
CYP inhibitory promiscuity	+	0.9048	90.48%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.7277	72.77%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.5985	59.85%
Skin irritation	-	0.8075	80.75%
Skin corrosion	-	0.9780	97.80%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7921	79.21%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	-	0.7572	75.72%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.7728	77.28%
Acute Oral Toxicity (c)	III	0.7198	71.98%
Estrogen receptor binding	+	0.8599	85.99%
Androgen receptor binding	+	0.7849	78.49%
Thyroid receptor binding	+	0.5264	52.64%
Glucocorticoid receptor binding	+	0.7816	78.16%
Aromatase binding	+	0.7850	78.50%
PPAR gamma	+	0.8719	87.19%
Honey bee toxicity	-	0.8420	84.20%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9949	99.49%

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	97.76%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.09%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.32%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.57%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.56%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.41%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.21%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	89.66%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.85%	96.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.81%	97.21%
CHEMBL2535	P11166	Glucose transporter	86.04%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.71%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.39%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.78%	89.62%

Plants that contains it

• Libanotis sibirica

Cross-Links

• PubChem: 12315487
• LOTUS: LTS0173199
• wikiData: Q104959469