methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-[[(2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl]-5-oxofuran-2-carboxylate

Details

• Internal ID: 96714eb0-b6ba-4912-b70f-1099d3bcf101
• Taxonomy: Organoheterocyclic compounds > Coumarans
• IUPAC Name: methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-[[(2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl]-5-oxofuran-2-carboxylate
• SMILES (Canonical): CC(C)(C1CC2=C(O1)C=CC(=C2)CC3(C(=C(C(=O)O3)O)C4=CC=C(C=C4)O)C(=O)OC)O
• SMILES (Isomeric): CC(C)([C@@H]1CC2=C(O1)C=CC(=C2)C[C@@]3(C(=C(C(=O)O3)O)C4=CC=C(C=C4)O)C(=O)OC)O
• InChI: InChI=1S/C24H24O8/c1-23(2,29)18-11-15-10-13(4-9-17(15)31-18)12-24(22(28)30-3)19(20(26)21(27)32-24)14-5-7-16(25)8-6-14/h4-10,18,25-26,29H,11-12H2,1-3H3/t18-,24+/m0/s1
• InChI Key: NVAIFFOQCAKMAH-MHECFPHRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₄O₈
• Molecular Weight: 440.40 g/mol
• Exact Mass: 440.14711772 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.45
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9886	98.86%
Caco-2	-	0.6910	69.10%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7601	76.01%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.8596	85.96%
OATP1B3 inhibitior	-	0.5205	52.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9538	95.38%
P-glycoprotein inhibitior	+	0.5840	58.40%
P-glycoprotein substrate	-	0.5145	51.45%
CYP3A4 substrate	+	0.6736	67.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8420	84.20%
CYP3A4 inhibition	-	0.6598	65.98%
CYP2C9 inhibition	+	0.6335	63.35%
CYP2C19 inhibition	-	0.5178	51.78%
CYP2D6 inhibition	-	0.8775	87.75%
CYP1A2 inhibition	-	0.7290	72.90%
CYP2C8 inhibition	+	0.8105	81.05%
CYP inhibitory promiscuity	+	0.6377	63.77%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.4331	43.31%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.8247	82.47%
Skin irritation	-	0.7665	76.65%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7256	72.56%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8003	80.03%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7999	79.99%
Acute Oral Toxicity (c)	I	0.4813	48.13%
Estrogen receptor binding	+	0.8175	81.75%
Androgen receptor binding	+	0.7571	75.71%
Thyroid receptor binding	+	0.6110	61.10%
Glucocorticoid receptor binding	+	0.7797	77.97%
Aromatase binding	+	0.6305	63.05%
PPAR gamma	+	0.7461	74.61%
Honey bee toxicity	-	0.7714	77.14%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.45%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.26%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.56%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.48%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.98%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.28%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.97%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.69%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.17%	99.17%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	90.92%	90.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.94%	95.89%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	88.70%	95.17%
CHEMBL3401	O75469	Pregnane X receptor	88.57%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.06%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.75%	95.89%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	85.63%	92.29%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.53%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.93%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	84.06%	91.19%
CHEMBL5555	O00767	Acyl-CoA desaturase	83.71%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.68%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.78%	95.50%
CHEMBL2535	P11166	Glucose transporter	82.46%	98.75%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.10%	97.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.02%	95.71%

Plants that contains it

• Diospyros sylvatica

Cross-Links

• PubChem: 51694600
• LOTUS: LTS0220650
• wikiData: Q105306626