[(1R,3R)-1-(3-Methoxy-4-hydroxyphenethyl)-3-hydroxy-5-(3,4-dihydroxyphenyl)pentyl]beta-D-glucopyranoside

Details

• Internal ID: edb6e7c3-b9d6-438c-88fc-843a57755d5b
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(3R,5R)-7-(3,4-dihydroxyphenyl)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)heptan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)CCC(CC(CCC2=CC(=C(C=C2)O)O)O)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CC[C@H](C[C@@H](CCC2=CC(=C(C=C2)O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C26H36O11/c1-35-21-11-15(5-9-19(21)30)3-7-17(36-26-25(34)24(33)23(32)22(13-27)37-26)12-16(28)6-2-14-4-8-18(29)20(31)10-14/h4-5,8-11,16-17,22-34H,2-3,6-7,12-13H2,1H3/t16-,17-,22-,23-,24+,25-,26-/m1/s1
• InChI Key: REBVNKVLUNZIRF-VZDPZUTLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₆O₁₁
• Molecular Weight: 524.60 g/mol
• Exact Mass: 524.22576196 g/mol
• Topological Polar Surface Area (TPSA): 190.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.31
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

• [(1R,3R)-1-(3-Methoxy-4-hydroxyphenethyl)-3-hydroxy-5-(3,4-dihydroxyphenyl)pentyl]beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6901	69.01%
Caco-2	-	0.8596	85.96%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7860	78.60%
OATP2B1 inhibitior	-	0.8627	86.27%
OATP1B1 inhibitior	+	0.8771	87.71%
OATP1B3 inhibitior	+	0.9400	94.00%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7292	72.92%
BSEP inhibitior	+	0.6686	66.86%
P-glycoprotein inhibitior	-	0.5909	59.09%
P-glycoprotein substrate	-	0.5349	53.49%
CYP3A4 substrate	+	0.6274	62.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7838	78.38%
CYP3A4 inhibition	-	0.8482	84.82%
CYP2C9 inhibition	-	0.8514	85.14%
CYP2C19 inhibition	-	0.8277	82.77%
CYP2D6 inhibition	-	0.8722	87.22%
CYP1A2 inhibition	-	0.8093	80.93%
CYP2C8 inhibition	+	0.5783	57.83%
CYP inhibitory promiscuity	-	0.8825	88.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7433	74.33%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9359	93.59%
Skin irritation	-	0.8102	81.02%
Skin corrosion	-	0.9532	95.32%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9249	92.49%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.8093	80.93%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8579	85.79%
Acute Oral Toxicity (c)	III	0.7423	74.23%
Estrogen receptor binding	+	0.8115	81.15%
Androgen receptor binding	+	0.5910	59.10%
Thyroid receptor binding	+	0.5830	58.30%
Glucocorticoid receptor binding	-	0.4809	48.09%
Aromatase binding	+	0.6015	60.15%
PPAR gamma	+	0.6424	64.24%
Honey bee toxicity	-	0.7170	71.70%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.7066	70.66%

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	99.67%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.28%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.71%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.49%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.93%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.73%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.23%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.24%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.73%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	84.53%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.25%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.99%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.06%	92.62%
CHEMBL2535	P11166	Glucose transporter	83.04%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.97%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.90%	99.15%
CHEMBL1255126	O15151	Protein Mdm4	81.71%	90.20%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.81%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.24%	95.56%

Plants that contains it

• Anthriscus sylvestris
• Tacca chantrieri

Cross-Links

• PubChem: 11005885
• NPASS: NPC177035
• LOTUS: LTS0211575
• wikiData: Q105234619