(2S,3R,4S,5S,6R)-2-[(8,9-dimethoxy-6a,8,9,11a-tetrahydro-6H-[1]benzofuro[3,2-c]chromen-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 4efcc90c-e9e2-44d4-a245-364a179975b9
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanols
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(8,9-dimethoxy-6a,8,9,11a-tetrahydro-6H-[1]benzofuro[3,2-c]chromen-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1C=C2C3COC4=C(C3OC2=CC1OC)C=CC(=C4)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC1C=C2C3COC4=C(C3OC2=CC1OC)C=CC(=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C23H28O10/c1-28-16-6-12-13-9-30-14-5-10(31-23-21(27)20(26)19(25)18(8-24)33-23)3-4-11(14)22(13)32-15(12)7-17(16)29-2/h3-7,13,16-27H,8-9H2,1-2H3/t13?,16?,17?,18-,19-,20+,21-,22?,23-/m1/s1
• InChI Key: JYAYJYYVTAWRDV-TXOKKQFOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₁₀
• Molecular Weight: 464.50 g/mol
• Exact Mass: 464.16824709 g/mol
• Topological Polar Surface Area (TPSA): 136.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.20
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7107	71.07%
Caco-2	-	0.8403	84.03%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6477	64.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9019	90.19%
OATP1B3 inhibitior	+	0.9653	96.53%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5307	53.07%
P-glycoprotein inhibitior	-	0.5758	57.58%
P-glycoprotein substrate	-	0.7230	72.30%
CYP3A4 substrate	+	0.6393	63.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8097	80.97%
CYP3A4 inhibition	-	0.8233	82.33%
CYP2C9 inhibition	-	0.7645	76.45%
CYP2C19 inhibition	-	0.5922	59.22%
CYP2D6 inhibition	-	0.7971	79.71%
CYP1A2 inhibition	-	0.7696	76.96%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.6530	65.30%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5612	56.12%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9432	94.32%
Skin irritation	-	0.7948	79.48%
Skin corrosion	-	0.9448	94.48%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6929	69.29%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	-	0.8552	85.52%
skin sensitisation	-	0.8000	80.00%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6857	68.57%
Acute Oral Toxicity (c)	III	0.5799	57.99%
Estrogen receptor binding	+	0.6870	68.70%
Androgen receptor binding	+	0.5994	59.94%
Thyroid receptor binding	+	0.5775	57.75%
Glucocorticoid receptor binding	-	0.5124	51.24%
Aromatase binding	-	0.5580	55.80%
PPAR gamma	+	0.6447	64.47%
Honey bee toxicity	-	0.7654	76.54%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.7887	78.87%

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	97.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.54%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.01%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.09%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.88%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.60%	86.33%
CHEMBL220	P22303	Acetylcholinesterase	91.36%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.18%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.05%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.47%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.13%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.98%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.68%	96.00%
CHEMBL4208	P20618	Proteasome component C5	85.02%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.11%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.68%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.78%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.91%	95.83%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.42%	100.00%

Plants that contains it

• Aquilaria sinensis

Cross-Links

• PubChem: 11968435
• NPASS: NPC24124