(2R)-5,11-dihydroxy-2,8,8-trimethyl-1,2-dihydro-[1]benzofuro[6,5-f]isochromene-4,9-dione

Details

• Internal ID: 79ff0802-ca48-4100-affe-12a55701bcb9
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (2R)-5,11-dihydroxy-2,8,8-trimethyl-1,2-dihydro-[1]benzofuro[6,5-f]isochromene-4,9-dione
• SMILES (Canonical): CC1CC2=C(C(=CC3=CC4=C(C(=C23)O)OC(=O)C4(C)C)O)C(=O)O1
• SMILES (Isomeric): C[C@@H]1CC2=C(C(=CC3=CC4=C(C(=C23)O)OC(=O)C4(C)C)O)C(=O)O1
• InChI: InChI=1S/C18H16O6/c1-7-4-9-12-8(6-11(19)13(9)16(21)23-7)5-10-15(14(12)20)24-17(22)18(10,2)3/h5-7,19-20H,4H2,1-3H3/t7-/m1/s1
• InChI Key: WJIFWGVKYPEREI-SSDOTTSWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₆
• Molecular Weight: 328.30 g/mol
• Exact Mass: 328.09468823 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 2.55
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9141	91.41%
Caco-2	+	0.6636	66.36%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7899	78.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8363	83.63%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8866	88.66%
P-glycoprotein inhibitior	-	0.8487	84.87%
P-glycoprotein substrate	-	0.7518	75.18%
CYP3A4 substrate	+	0.5917	59.17%
CYP2C9 substrate	+	0.6330	63.30%
CYP2D6 substrate	-	0.8514	85.14%
CYP3A4 inhibition	-	0.8882	88.82%
CYP2C9 inhibition	-	0.5964	59.64%
CYP2C19 inhibition	-	0.8404	84.04%
CYP2D6 inhibition	-	0.8678	86.78%
CYP1A2 inhibition	-	0.6310	63.10%
CYP2C8 inhibition	-	0.7279	72.79%
CYP inhibitory promiscuity	-	0.8470	84.70%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.3816	38.16%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.5766	57.66%
Skin irritation	-	0.7391	73.91%
Skin corrosion	-	0.9054	90.54%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6895	68.95%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8217	82.17%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6038	60.38%
Acute Oral Toxicity (c)	III	0.4136	41.36%
Estrogen receptor binding	+	0.8788	87.88%
Androgen receptor binding	+	0.6538	65.38%
Thyroid receptor binding	-	0.5063	50.63%
Glucocorticoid receptor binding	+	0.6222	62.22%
Aromatase binding	+	0.6120	61.20%
PPAR gamma	+	0.6609	66.09%
Honey bee toxicity	-	0.8687	86.87%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9795	97.95%

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	99.45%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.43%	91.49%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	92.79%	85.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.96%	99.23%
CHEMBL2581	P07339	Cathepsin D	91.81%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.18%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.85%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.93%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.76%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.21%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.02%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.57%	99.15%
CHEMBL4208	P20618	Proteasome component C5	80.24%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.09%	92.94%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162915817
• LOTUS: LTS0144908
• wikiData: Q105306805