(2S,3S,4R,5S,6S)-5-[(2R,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[[(1R,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-2-(hydroxymethyl)oxane-3,4-diol

Details

• Internal ID: 6bcb422b-7253-4693-b404-cf863ff74534
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2S,3S,4R,5S,6S)-5-[(2R,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[[(1R,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-2-(hydroxymethyl)oxane-3,4-diol
• SMILES (Canonical): COC1=C(C=C2C(C(C(CC2=C1)CO)COC3C(C(C(C(O3)CO)O)O)OC4C(C(CO4)(CO)O)O)C5=CC(=C(C=C5)O)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[C@@H]4[C@@H]([C@@](CO4)(CO)O)O)C5=CC(=C(C=C5)O)OC)O
• InChI: InChI=1S/C31H42O15/c1-41-21-6-14(3-4-19(21)35)24-17-8-20(36)22(42-2)7-15(17)5-16(9-32)18(24)11-43-29-27(26(38)25(37)23(10-33)45-29)46-30-28(39)31(40,12-34)13-44-30/h3-4,6-8,16,18,23-30,32-40H,5,9-13H2,1-2H3/t16-,18-,23-,24+,25+,26+,27-,28-,29-,30+,31-/m0/s1
• InChI Key: YBUMLRJVGYOZOE-ZICOSUORSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₂O₁₅
• Molecular Weight: 654.70 g/mol
• Exact Mass: 654.25237063 g/mol
• Topological Polar Surface Area (TPSA): 237.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.69
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6040	60.40%
Caco-2	-	0.8784	87.84%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6147	61.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8629	86.29%
OATP1B3 inhibitior	+	0.9660	96.60%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7846	78.46%
P-glycoprotein inhibitior	-	0.4474	44.74%
P-glycoprotein substrate	+	0.5315	53.15%
CYP3A4 substrate	+	0.6852	68.52%
CYP2C9 substrate	-	0.8016	80.16%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	-	0.8606	86.06%
CYP2C9 inhibition	-	0.9049	90.49%
CYP2C19 inhibition	-	0.8316	83.16%
CYP2D6 inhibition	-	0.8953	89.53%
CYP1A2 inhibition	-	0.8731	87.31%
CYP2C8 inhibition	+	0.6883	68.83%
CYP inhibitory promiscuity	-	0.7456	74.56%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5242	52.42%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9323	93.23%
Skin irritation	-	0.8164	81.64%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8390	83.90%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8825	88.25%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7822	78.22%
Acute Oral Toxicity (c)	III	0.6494	64.94%
Estrogen receptor binding	+	0.8247	82.47%
Androgen receptor binding	+	0.6481	64.81%
Thyroid receptor binding	+	0.5454	54.54%
Glucocorticoid receptor binding	+	0.5911	59.11%
Aromatase binding	+	0.6025	60.25%
PPAR gamma	+	0.6617	66.17%
Honey bee toxicity	-	0.7387	73.87%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.7908	79.08%

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	99.88%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.04%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	97.11%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.47%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.23%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.22%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.20%	95.89%
CHEMBL2581	P07339	Cathepsin D	89.59%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.61%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.19%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.55%	89.00%
CHEMBL4208	P20618	Proteasome component C5	86.98%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.28%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.28%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.03%	96.00%
CHEMBL4581	P52732	Kinesin-like protein 1	84.78%	93.18%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.18%	97.36%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.30%	89.62%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.18%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.95%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.97%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	80.88%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.47%	95.83%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.22%	97.14%

Plants that contains it

• Breynia androgyna

Cross-Links

• PubChem: 163186033
• LOTUS: LTS0003912
• wikiData: Q105346063