4-[(2S,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol

Details

• Internal ID: cb340ac1-44d2-4401-9969-48cb8456f523
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 4-[(2S,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol
• InChI: InChI=1S/C19H22O6/c1-24-17-8-11(3-2-6-20)7-13-14(10-21)18(25-19(13)17)12-4-5-15(22)16(23)9-12/h4-5,7-9,14,18,20-23H,2-3,6,10H2,1H3/t14-,18+/m0/s1
• InChI Key: BRXZKNYGADMTLG-KBXCAEBGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.14163842 g/mol
• Topological Polar Surface Area (TPSA): 99.40 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.24
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9763	97.63%
Caco-2	-	0.6052	60.52%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7798	77.98%
OATP2B1 inhibitior	-	0.5797	57.97%
OATP1B1 inhibitior	+	0.8461	84.61%
OATP1B3 inhibitior	+	0.9653	96.53%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5528	55.28%
P-glycoprotein inhibitior	-	0.6713	67.13%
P-glycoprotein substrate	-	0.6415	64.15%
CYP3A4 substrate	+	0.6025	60.25%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	+	0.4613	46.13%
CYP3A4 inhibition	-	0.8472	84.72%
CYP2C9 inhibition	-	0.6338	63.38%
CYP2C19 inhibition	-	0.5336	53.36%
CYP2D6 inhibition	-	0.8968	89.68%
CYP1A2 inhibition	+	0.5947	59.47%
CYP2C8 inhibition	+	0.8191	81.91%
CYP inhibitory promiscuity	-	0.5378	53.78%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5132	51.32%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.8243	82.43%
Skin irritation	-	0.7913	79.13%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7024	70.24%
Micronuclear	-	0.5241	52.41%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8329	83.29%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.5631	56.31%
Acute Oral Toxicity (c)	III	0.7076	70.76%
Estrogen receptor binding	+	0.7957	79.57%
Androgen receptor binding	+	0.7073	70.73%
Thyroid receptor binding	+	0.7655	76.55%
Glucocorticoid receptor binding	+	0.7148	71.48%
Aromatase binding	+	0.5346	53.46%
PPAR gamma	+	0.6219	62.19%
Honey bee toxicity	-	0.8694	86.94%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6449	64.49%
Fish aquatic toxicity	-	0.4603	46.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.49%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.74%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.39%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.72%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.67%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	91.11%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.93%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.53%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.48%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.78%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	82.36%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.65%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.63%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.40%	95.89%

Plants that contains it

• Taxus mairei

Cross-Links

• PubChem: 163187620
• LOTUS: LTS0246066
• wikiData: Q104945083