5-Methoxyseselin

Details

• Internal ID: b676427e-ad5e-40c7-adbf-254b4df70ea5
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: 5-methoxy-8,8-dimethylpyrano[2,3-f]chromen-2-one
• SMILES (Canonical): CC1(C=CC2=C3C(=C(C=C2O1)OC)C=CC(=O)O3)C
• SMILES (Isomeric): CC1(C=CC2=C3C(=C(C=C2O1)OC)C=CC(=O)O3)C
• InChI: InChI=1S/C15H14O4/c1-15(2)7-6-10-12(19-15)8-11(17-3)9-4-5-13(16)18-14(9)10/h4-8H,1-3H3
• InChI Key: ZNMRQYJUVCXNGK-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27 g/mol
• Exact Mass: 258.08920892 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.99
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 31525-76-5
• 5-methoxy-8,8-dimethyl-2h,8h-pyrano[2,3-f]chromen-2-one
• CHEMBL479894
• NSC 155351
• NSC155351
• DTXSID80302933
• CHEBI:174378
• BDBM50008732
• NSC-155351
• 5-methoxy-8,8-dimethylpyrano[2,3-]chromen-2-one
• 5-methoxy-8,8-dimethyl-pyrano[2,3-f]chromen-2-one
• 5-Methoxy-8,8-dimethylpyrano[2,3-f]chromen-2(8H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9892	98.92%
Caco-2	+	0.8779	87.79%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6940	69.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9457	94.57%
OATP1B3 inhibitior	+	0.9755	97.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5639	56.39%
P-glycoprotein inhibitior	-	0.5926	59.26%
P-glycoprotein substrate	-	0.7301	73.01%
CYP3A4 substrate	+	0.5215	52.15%
CYP2C9 substrate	-	0.6755	67.55%
CYP2D6 substrate	-	0.8349	83.49%
CYP3A4 inhibition	+	0.5583	55.83%
CYP2C9 inhibition	-	0.7827	78.27%
CYP2C19 inhibition	+	0.6475	64.75%
CYP2D6 inhibition	-	0.7376	73.76%
CYP1A2 inhibition	+	0.6377	63.77%
CYP2C8 inhibition	-	0.6503	65.03%
CYP inhibitory promiscuity	+	0.6134	61.34%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Danger	0.5268	52.68%
Eye corrosion	-	0.9695	96.95%
Eye irritation	+	0.8753	87.53%
Skin irritation	-	0.7952	79.52%
Skin corrosion	-	0.9812	98.12%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6714	67.14%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.6699	66.99%
skin sensitisation	-	0.8176	81.76%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.6032	60.32%
Acute Oral Toxicity (c)	III	0.4420	44.20%
Estrogen receptor binding	+	0.9039	90.39%
Androgen receptor binding	+	0.7400	74.00%
Thyroid receptor binding	+	0.6304	63.04%
Glucocorticoid receptor binding	+	0.8176	81.76%
Aromatase binding	+	0.8376	83.76%
PPAR gamma	+	0.7739	77.39%
Honey bee toxicity	-	0.7705	77.05%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9755	97.55%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL288	Q08499	Phosphodiesterase 4D	1870 nM	IC50	PMID: 24597921

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.49%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.98%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.80%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.68%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.78%	94.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.86%	85.30%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	85.03%	94.03%
CHEMBL2535	P11166	Glucose transporter	84.16%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.70%	89.00%
CHEMBL1255126	O15151	Protein Mdm4	83.61%	90.20%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.06%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.79%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.28%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.04%	86.33%

Plants that contains it

• Citrus × aurantium
• Citrus maxima
• Citrus medica
• Clematis flammula
• Gentianella magellanica
• Hortia brasiliana
• Lysimachia arvensis
• Murraya alata
• Plumbago zeylanica
• Swinglea glutinosa
• Toddalia asiatica
• Uncaria perrottetii

Cross-Links

• PubChem: 290897
• NPASS: NPC173350
• ChEMBL: CHEMBL479894
• LOTUS: LTS0086567
• wikiData: Q82048003