methyl (4S,5E,6S)-4-[2-[[(2R,3S,4S,5R,6S)-6-[[(3R,3aS,6S,6aR)-3,6-bis(4-hydroxy-3-methoxyphenyl)-3,4,6,6a-tetrahydro-1H-furo[3,4-c]furan-3a-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Details

• Internal ID: 09c206a9-a3bf-45ac-9abe-d8f73ccb7592
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: methyl (4S,5E,6S)-4-[2-[[(2R,3S,4S,5R,6S)-6-[[(3R,3aS,6S,6aR)-3,6-bis(4-hydroxy-3-methoxyphenyl)-3,4,6,6a-tetrahydro-1H-furo[3,4-c]furan-3a-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• SMILES (Canonical): CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCC3C(C(C(C(O3)OC45COC(C4COC5C6=CC(=C(C=C6)O)OC)C7=CC(=C(C=C7)O)OC)O)O)O
• SMILES (Isomeric): C/C=C/1\[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)O[C@]45CO[C@@H]([C@H]4CO[C@@H]5C6=CC(=C(C=C6)O)OC)C7=CC(=C(C=C7)O)OC)O)O)O
• InChI: InChI=1S/C43H54O22/c1-5-20-21(22(39(54)57-4)14-60-40(20)64-41-35(52)33(50)31(48)28(13-44)62-41)12-30(47)58-16-29-32(49)34(51)36(53)42(63-29)65-43-17-61-37(18-6-8-24(45)26(10-18)55-2)23(43)15-59-38(43)19-7-9-25(46)27(11-19)56-3/h5-11,14,21,23,28-29,31-38,40-42,44-46,48-53H,12-13,15-17H2,1-4H3/b20-5+/t21-,23+,28+,29+,31+,32+,33-,34-,35+,36+,37+,38+,40-,41-,42-,43+/m0/s1
• InChI Key: URBPIXMUXQEKHZ-AKZJQTFZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₅₄O₂₂
• Molecular Weight: 922.90 g/mol
• Exact Mass: 922.31067335 g/mol
• Topological Polar Surface Area (TPSA): 318.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -1.14
• H-Bond Acceptor: 22
• H-Bond Donor: 9
• Rotatable Bonds: 14

Synonyms

• 114449-12-6
• AKOS040736277

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7543	75.43%
Caco-2	-	0.8703	87.03%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7378	73.78%
OATP2B1 inhibitior	-	0.8636	86.36%
OATP1B1 inhibitior	+	0.7728	77.28%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8735	87.35%
P-glycoprotein inhibitior	+	0.7433	74.33%
P-glycoprotein substrate	+	0.6962	69.62%
CYP3A4 substrate	+	0.7207	72.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8676	86.76%
CYP3A4 inhibition	-	0.8013	80.13%
CYP2C9 inhibition	-	0.8065	80.65%
CYP2C19 inhibition	-	0.7766	77.66%
CYP2D6 inhibition	-	0.9431	94.31%
CYP1A2 inhibition	-	0.8619	86.19%
CYP2C8 inhibition	+	0.8300	83.00%
CYP inhibitory promiscuity	-	0.6842	68.42%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5712	57.12%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9063	90.63%
Skin irritation	-	0.7852	78.52%
Skin corrosion	-	0.9442	94.42%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7521	75.21%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.7591	75.91%
skin sensitisation	-	0.8406	84.06%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7898	78.98%
Acute Oral Toxicity (c)	I	0.4652	46.52%
Estrogen receptor binding	+	0.8211	82.11%
Androgen receptor binding	+	0.7164	71.64%
Thyroid receptor binding	+	0.5674	56.74%
Glucocorticoid receptor binding	+	0.7520	75.20%
Aromatase binding	+	0.5568	55.68%
PPAR gamma	+	0.7831	78.31%
Honey bee toxicity	-	0.6918	69.18%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9863	98.63%

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	99.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.11%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.69%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.64%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.02%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.74%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.14%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.85%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.85%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.13%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	90.01%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.31%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.77%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	88.13%	91.19%
CHEMBL5028	O14672	ADAM10	88.09%	97.50%
CHEMBL2581	P07339	Cathepsin D	86.64%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.33%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	86.26%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.15%	97.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.74%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.79%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.12%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.72%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.32%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.16%	89.62%

Plants that contains it

• Jasminum sambac

Cross-Links

• PubChem: 75412002
• LOTUS: LTS0039765
• wikiData: Q105277649