5-[(6S)-6-(2-hydroxypropan-2-yl)-5,6-dihydrofuro[3,2-f][1]benzofuran-2-yl]benzene-1,3-diol

Details

• Internal ID: 7049e68b-1a08-4df1-80d7-d76b1a77f3bb
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-[(6S)-6-(2-hydroxypropan-2-yl)-5,6-dihydrofuro[3,2-f][1]benzofuran-2-yl]benzene-1,3-diol
• SMILES (Canonical): CC(C)(C1CC2=C(O1)C=C3C(=C2)C=C(O3)C4=CC(=CC(=C4)O)O)O
• SMILES (Isomeric): CC(C)([C@@H]1CC2=C(O1)C=C3C(=C2)C=C(O3)C4=CC(=CC(=C4)O)O)O
• InChI: InChI=1S/C19H18O5/c1-19(2,22)18-7-11-3-10-6-15(23-16(10)9-17(11)24-18)12-4-13(20)8-14(21)5-12/h3-6,8-9,18,20-22H,7H2,1-2H3/t18-/m0/s1
• InChI Key: HMTMYIWMPJSCAZ-SFHVURJKSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₅
• Molecular Weight: 326.30 g/mol
• Exact Mass: 326.11542367 g/mol
• Topological Polar Surface Area (TPSA): 83.10 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.59
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9878	98.78%
Caco-2	-	0.5322	53.22%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7387	73.87%
OATP2B1 inhibitior	-	0.7123	71.23%
OATP1B1 inhibitior	+	0.9268	92.68%
OATP1B3 inhibitior	+	0.9008	90.08%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6924	69.24%
P-glycoprotein inhibitior	-	0.5719	57.19%
P-glycoprotein substrate	-	0.6951	69.51%
CYP3A4 substrate	+	0.5313	53.13%
CYP2C9 substrate	-	0.5960	59.60%
CYP2D6 substrate	+	0.3973	39.73%
CYP3A4 inhibition	-	0.7473	74.73%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	-	0.6178	61.78%
CYP2D6 inhibition	-	0.8000	80.00%
CYP1A2 inhibition	-	0.6320	63.20%
CYP2C8 inhibition	+	0.5847	58.47%
CYP inhibitory promiscuity	+	0.5814	58.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4736	47.36%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.6392	63.92%
Skin irritation	-	0.7586	75.86%
Skin corrosion	-	0.9095	90.95%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8573	85.73%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	-	0.6208	62.08%
skin sensitisation	-	0.7896	78.96%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7451	74.51%
Acute Oral Toxicity (c)	III	0.7043	70.43%
Estrogen receptor binding	+	0.9370	93.70%
Androgen receptor binding	+	0.5683	56.83%
Thyroid receptor binding	+	0.6878	68.78%
Glucocorticoid receptor binding	+	0.6312	63.12%
Aromatase binding	+	0.7640	76.40%
PPAR gamma	+	0.8595	85.95%
Honey bee toxicity	-	0.9057	90.57%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9372	93.72%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	0.14 nM; 6.76 nM	IC50; IC50	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.96%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.47%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.08%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.05%	95.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.07%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.32%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.08%	97.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.98%	85.11%

Plants that contains it

• Morus alba
• Morus cathayana
• Morus nigra

Cross-Links

• PubChem: 42603436
• LOTUS: LTS0273046
• wikiData: Q105030677