1-[(2R,7S)-4-hydroxy-2,7-bis(2-hydroxypropan-2-yl)-2,3,7,8-tetrahydrofuro[2,3-e][1]benzofuran-5-yl]-2-methylpropan-1-one

Details

• Internal ID: 919167b5-38b2-4542-b874-9c6a2da79b4d
• Taxonomy: Organoheterocyclic compounds > Coumarans
• IUPAC Name: 1-[(2R,7S)-4-hydroxy-2,7-bis(2-hydroxypropan-2-yl)-2,3,7,8-tetrahydrofuro[2,3-e][1]benzofuran-5-yl]-2-methylpropan-1-one
• SMILES (Canonical): CC(C)C(=O)C1=C2C(=C3C(=C1O)CC(O3)C(C)(C)O)CC(O2)C(C)(C)O
• SMILES (Isomeric): CC(C)C(=O)C1=C2C(=C3C(=C1O)C[C@@H](O3)C(C)(C)O)C[C@H](O2)C(C)(C)O
• InChI: InChI=1S/C20H28O6/c1-9(2)15(21)14-16(22)10-7-12(19(3,4)23)25-17(10)11-8-13(20(5,6)24)26-18(11)14/h9,12-13,22-24H,7-8H2,1-6H3/t12-,13+/m1/s1
• InChI Key: VPBDCGLRLMBBMF-OLZOCXBDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.40 g/mol
• Exact Mass: 364.18858861 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	-	0.5749	57.49%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8219	82.19%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.8997	89.97%
OATP1B3 inhibitior	+	0.9249	92.49%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8488	84.88%
P-glycoprotein inhibitior	-	0.6831	68.31%
P-glycoprotein substrate	-	0.8524	85.24%
CYP3A4 substrate	+	0.5120	51.20%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.8021	80.21%
CYP3A4 inhibition	-	0.9186	91.86%
CYP2C9 inhibition	-	0.8593	85.93%
CYP2C19 inhibition	-	0.7872	78.72%
CYP2D6 inhibition	-	0.9202	92.02%
CYP1A2 inhibition	+	0.5348	53.48%
CYP2C8 inhibition	-	0.8548	85.48%
CYP inhibitory promiscuity	-	0.8455	84.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5592	55.92%
Eye corrosion	-	0.9826	98.26%
Eye irritation	+	0.6127	61.27%
Skin irritation	-	0.6534	65.34%
Skin corrosion	-	0.8820	88.20%
Ames mutagenesis	-	0.7054	70.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7134	71.34%
Micronuclear	-	0.5741	57.41%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.6825	68.25%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7739	77.39%
Acute Oral Toxicity (c)	III	0.6292	62.92%
Estrogen receptor binding	+	0.8363	83.63%
Androgen receptor binding	+	0.5490	54.90%
Thyroid receptor binding	+	0.6873	68.73%
Glucocorticoid receptor binding	+	0.7262	72.62%
Aromatase binding	+	0.5879	58.79%
PPAR gamma	+	0.8763	87.63%
Honey bee toxicity	-	0.9047	90.47%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9388	93.88%

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	98.20%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.53%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.25%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.17%	93.56%
CHEMBL3401	O75469	Pregnane X receptor	87.14%	94.73%
CHEMBL2581	P07339	Cathepsin D	85.24%	98.95%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.18%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	82.04%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.01%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.63%	92.62%

Plants that contains it

• Garcinia subelliptica

Cross-Links

• PubChem: 24774694
• LOTUS: LTS0120265
• wikiData: Q105290625