(9-Acetyloxy-8,8-dimethyl-2-oxo-3,4,9,10-tetrahydropyrano[2,3-f]chromen-10-yl) 3-methylbut-2-enoate

Details

• Internal ID: 116bd0b1-bec3-42d9-aea7-d6987fc34ce5
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: (9-acetyloxy-8,8-dimethyl-2-oxo-3,4,9,10-tetrahydropyrano[2,3-f]chromen-10-yl) 3-methylbut-2-enoate
• SMILES (Canonical): CC(=CC(=O)OC1C(C(OC2=C1C3=C(CCC(=O)O3)C=C2)(C)C)OC(=O)C)C
• SMILES (Isomeric): CC(=CC(=O)OC1C(C(OC2=C1C3=C(CCC(=O)O3)C=C2)(C)C)OC(=O)C)C
• InChI: InChI=1S/C21H24O7/c1-11(2)10-16(24)27-19-17-14(28-21(4,5)20(19)25-12(3)22)8-6-13-7-9-15(23)26-18(13)17/h6,8,10,19-20H,7,9H2,1-5H3
• InChI Key: TZFHWBOBWQNLFR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₇
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.15220310 g/mol
• Topological Polar Surface Area (TPSA): 88.10 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9826	98.26%
Caco-2	+	0.6877	68.77%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8060	80.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9097	90.97%
OATP1B3 inhibitior	+	0.9290	92.90%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.8709	87.09%
P-glycoprotein inhibitior	+	0.7483	74.83%
P-glycoprotein substrate	-	0.7557	75.57%
CYP3A4 substrate	+	0.6566	65.66%
CYP2C9 substrate	-	0.8150	81.50%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	+	0.5077	50.77%
CYP2C9 inhibition	-	0.7221	72.21%
CYP2C19 inhibition	+	0.5778	57.78%
CYP2D6 inhibition	-	0.8101	81.01%
CYP1A2 inhibition	-	0.5564	55.64%
CYP2C8 inhibition	+	0.5469	54.69%
CYP inhibitory promiscuity	-	0.5248	52.48%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9818	98.18%
Carcinogenicity (trinary)	Non-required	0.4590	45.90%
Eye corrosion	-	0.9851	98.51%
Eye irritation	-	0.8635	86.35%
Skin irritation	-	0.7361	73.61%
Skin corrosion	-	0.9327	93.27%
Ames mutagenesis	+	0.6009	60.09%
Human Ether-a-go-go-Related Gene inhibition	+	0.7257	72.57%
Micronuclear	-	0.6141	61.41%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.6463	64.63%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.4637	46.37%
Acute Oral Toxicity (c)	III	0.6566	65.66%
Estrogen receptor binding	+	0.7985	79.85%
Androgen receptor binding	+	0.6459	64.59%
Thyroid receptor binding	-	0.5358	53.58%
Glucocorticoid receptor binding	+	0.7086	70.86%
Aromatase binding	-	0.5847	58.47%
PPAR gamma	+	0.6462	64.62%
Honey bee toxicity	-	0.6816	68.16%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9659	96.59%

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	99.05%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	98.90%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.51%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.50%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.26%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.48%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.92%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.25%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.65%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.96%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.33%	95.89%

Plants that contains it

• Prionosciadium thapsoides

Cross-Links

• PubChem: 163094399
• LOTUS: LTS0086507
• wikiData: Q105268106