(2S,3S)-3-(hydroxymethyl)-4,6-dimethoxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-5-ol

Details

• Internal ID: 9975bc4e-6833-449c-94f5-e746bd604e63
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3S)-3-(hydroxymethyl)-4,6-dimethoxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-5-ol
• InChI: InChI=1S/C20H24O8/c1-23-13-8-12-16(20(27-5)17(13)22)11(9-21)18(28-12)10-6-14(24-2)19(26-4)15(7-10)25-3/h6-8,11,18,21-22H,9H2,1-5H3/t11-,18-/m1/s1
• InChI Key: INACKEYIIKMUED-ADLMAVQZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₈
• Molecular Weight: 392.40 g/mol
• Exact Mass: 392.14711772 g/mol
• Topological Polar Surface Area (TPSA): 95.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9827	98.27%
Caco-2	+	0.6716	67.16%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7594	75.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8300	83.00%
OATP1B3 inhibitior	+	0.7931	79.31%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5921	59.21%
P-glycoprotein inhibitior	-	0.5923	59.23%
P-glycoprotein substrate	-	0.8345	83.45%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7846	78.46%
CYP2D6 substrate	+	0.4313	43.13%
CYP3A4 inhibition	-	0.6222	62.22%
CYP2C9 inhibition	+	0.8288	82.88%
CYP2C19 inhibition	+	0.7963	79.63%
CYP2D6 inhibition	-	0.8336	83.36%
CYP1A2 inhibition	+	0.7340	73.40%
CYP2C8 inhibition	+	0.6030	60.30%
CYP inhibitory promiscuity	+	0.9272	92.72%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9308	93.08%
Carcinogenicity (trinary)	Non-required	0.5017	50.17%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.5504	55.04%
Skin irritation	-	0.8247	82.47%
Skin corrosion	-	0.9682	96.82%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5684	56.84%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8384	83.84%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8090	80.90%
Acute Oral Toxicity (c)	III	0.6013	60.13%
Estrogen receptor binding	+	0.8056	80.56%
Androgen receptor binding	+	0.5473	54.73%
Thyroid receptor binding	+	0.7870	78.70%
Glucocorticoid receptor binding	+	0.6488	64.88%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.5257	52.57%
Honey bee toxicity	-	0.8807	88.07%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.8774	87.74%

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	97.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.06%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.22%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.24%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.21%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.17%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.31%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.32%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.94%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.24%	97.09%

Plants that contains it

• Tarenna attenuata

Cross-Links

• PubChem: 16216402
• LOTUS: LTS0267244
• wikiData: Q105116042