(2R,3R,4S,5S,6R)-2-[[(1S,2S,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: ba58f3e8-a077-447a-bd1b-8575e2e45691
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(1S,2S,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C(=C2C(C(C(CC2=C1)CO)COC3C(C(C(C(O3)CO)O)O)O)C4=CC(=C(C=C4)O)OC)OC)O
• SMILES (Isomeric): COC1=C(C(=C2[C@@H]([C@@H]([C@@H](CC2=C1)CO)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C4=CC(=C(C=C4)O)OC)OC)O
• InChI: InChI=1S/C27H36O12/c1-35-17-7-12(4-5-16(17)30)20-15(11-38-27-25(34)24(33)22(31)19(10-29)39-27)14(9-28)6-13-8-18(36-2)23(32)26(37-3)21(13)20/h4-5,7-8,14-15,19-20,22,24-25,27-34H,6,9-11H2,1-3H3/t14-,15+,19+,20+,22+,24-,25+,27+/m0/s1
• InChI Key: SYBBJIZIKGGETQ-WWSWEYQKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₁₂
• Molecular Weight: 552.60 g/mol
• Exact Mass: 552.22067658 g/mol
• Topological Polar Surface Area (TPSA): 188.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.15
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5464	54.64%
Caco-2	-	0.8250	82.50%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5820	58.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8503	85.03%
OATP1B3 inhibitior	+	0.9597	95.97%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5052	50.52%
P-glycoprotein inhibitior	-	0.5748	57.48%
P-glycoprotein substrate	-	0.6656	66.56%
CYP3A4 substrate	+	0.6112	61.12%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.7492	74.92%
CYP3A4 inhibition	-	0.9149	91.49%
CYP2C9 inhibition	-	0.8886	88.86%
CYP2C19 inhibition	-	0.8106	81.06%
CYP2D6 inhibition	-	0.9246	92.46%
CYP1A2 inhibition	-	0.7947	79.47%
CYP2C8 inhibition	+	0.6555	65.55%
CYP inhibitory promiscuity	-	0.6489	64.89%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6531	65.31%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9344	93.44%
Skin irritation	-	0.8512	85.12%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7417	74.17%
Micronuclear	+	0.6059	60.59%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9256	92.56%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.9381	93.81%
Acute Oral Toxicity (c)	III	0.6648	66.48%
Estrogen receptor binding	+	0.8088	80.88%
Androgen receptor binding	+	0.6584	65.84%
Thyroid receptor binding	+	0.5777	57.77%
Glucocorticoid receptor binding	+	0.6066	60.66%
Aromatase binding	+	0.5183	51.83%
PPAR gamma	+	0.5841	58.41%
Honey bee toxicity	-	0.8204	82.04%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8364	83.64%

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	99.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.78%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.92%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.37%	89.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.61%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.22%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.80%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.46%	92.94%
CHEMBL2581	P07339	Cathepsin D	87.01%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	86.98%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.55%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.43%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.29%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.94%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.66%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.92%	96.00%
CHEMBL4208	P20618	Proteasome component C5	83.27%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.45%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.05%	95.56%

Plants that contains it

• Annona squamosa

Cross-Links

• PubChem: 101383540
• LOTUS: LTS0242660
• wikiData: Q105263453