4-[(2R,3S,3aR,5R,6aR)-5-(furan-3-yl)-2,3-dimethyl-3,4,5,6a-tetrahydro-2H-furo[2,3-b]furan-3a-yl]-3H-2-benzofuran-1-one

Details

• Internal ID: 054bcda3-df3d-4a54-8fbe-f064c136f18d
• Taxonomy: Organoheterocyclic compounds > Isocoumarans > Isobenzofuranones > Phthalides
• IUPAC Name: 4-[(2R,3S,3aR,5R,6aR)-5-(furan-3-yl)-2,3-dimethyl-3,4,5,6a-tetrahydro-2H-furo[2,3-b]furan-3a-yl]-3H-2-benzofuran-1-one
• SMILES (Canonical): CC1C(OC2C1(CC(O2)C3=COC=C3)C4=CC=CC5=C4COC5=O)C
• SMILES (Isomeric): C[C@@H]1[C@H](O[C@H]2[C@@]1(C[C@@H](O2)C3=COC=C3)C4=CC=CC5=C4COC5=O)C
• InChI: InChI=1S/C20H20O5/c1-11-12(2)24-19-20(11,8-17(25-19)13-6-7-22-9-13)16-5-3-4-14-15(16)10-23-18(14)21/h3-7,9,11-12,17,19H,8,10H2,1-2H3/t11-,12-,17-,19-,20-/m1/s1
• InChI Key: CTDRGEIVHYZZCA-IKICYEBISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.40 g/mol
• Exact Mass: 340.13107373 g/mol
• Topological Polar Surface Area (TPSA): 57.90 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.73
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.7017	70.17%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7189	71.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8809	88.09%
OATP1B3 inhibitior	+	0.9423	94.23%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7821	78.21%
P-glycoprotein inhibitior	-	0.4884	48.84%
P-glycoprotein substrate	-	0.5644	56.44%
CYP3A4 substrate	+	0.6262	62.62%
CYP2C9 substrate	-	0.5802	58.02%
CYP2D6 substrate	-	0.8677	86.77%
CYP3A4 inhibition	-	0.8413	84.13%
CYP2C9 inhibition	-	0.7889	78.89%
CYP2C19 inhibition	-	0.7171	71.71%
CYP2D6 inhibition	-	0.9577	95.77%
CYP1A2 inhibition	-	0.7872	78.72%
CYP2C8 inhibition	-	0.6854	68.54%
CYP inhibitory promiscuity	-	0.8431	84.31%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6314	63.14%
Eye corrosion	-	0.9844	98.44%
Eye irritation	-	0.9625	96.25%
Skin irritation	-	0.7700	77.00%
Skin corrosion	-	0.9213	92.13%
Ames mutagenesis	+	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6431	64.31%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.6784	67.84%
skin sensitisation	-	0.7657	76.57%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.7464	74.64%
Acute Oral Toxicity (c)	III	0.4920	49.20%
Estrogen receptor binding	+	0.8501	85.01%
Androgen receptor binding	+	0.6107	61.07%
Thyroid receptor binding	-	0.6400	64.00%
Glucocorticoid receptor binding	+	0.7335	73.35%
Aromatase binding	+	0.6782	67.82%
PPAR gamma	+	0.6315	63.15%
Honey bee toxicity	-	0.8774	87.74%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9808	98.08%

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	94.84%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.19%	93.40%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.90%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.85%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.69%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.26%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	91.12%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.39%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.63%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.37%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	87.57%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.07%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.96%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.19%	99.23%
CHEMBL3038469	P24941	CDK2/Cyclin A	85.98%	91.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.88%	94.00%
CHEMBL4208	P20618	Proteasome component C5	85.36%	90.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.90%	90.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.68%	82.69%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.34%	97.33%
CHEMBL1907	P15144	Aminopeptidase N	82.32%	93.31%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.77%	100.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.54%	96.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.06%	97.14%

Plants that contains it

• Salvia rhyacophila

Cross-Links

• PubChem: 137659006
• LOTUS: LTS0238467
• wikiData: Q104969735