bis[[(1S,3S,4S)-4-formyl-3-hydroxy-4-[(Z)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethenyl]cyclohexyl]methyl] (1R,2S)-6,7-dihydroxy-1-(4-hydroxyphenyl)-1,2-dihydronaphthalene-2,3-dicarboxylate

Details

• Internal ID: 54eea06a-5d5a-4dbc-8a03-5fbb26b44b2d
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: bis[[(1S,3S,4S)-4-formyl-3-hydroxy-4-[(Z)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethenyl]cyclohexyl]methyl] (1R,2S)-6,7-dihydroxy-1-(4-hydroxyphenyl)-1,2-dihydronaphthalene-2,3-dicarboxylate
• SMILES (Canonical): C1CC(C(CC1COC(=O)C2C(C3=CC(=C(C=C3C=C2C(=O)OCC4CCC(C(C4)O)(C=COC5C(C(C(C(O5)CO)O)O)O)C=O)O)O)C6=CC=C(C=C6)O)O)(C=COC7C(C(C(C(O7)CO)O)O)O)C=O
• SMILES (Isomeric): C1C[C@@]([C@H](C[C@H]1COC(=O)[C@H]2[C@@H](C3=CC(=C(C=C3C=C2C(=O)OC[C@H]4CC[C@@]([C@H](C4)O)(/C=C\O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C=O)O)O)C6=CC=C(C=C6)O)O)(/C=C\O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C=O
• InChI: InChI=1S/C50H62O23/c51-18-33-39(60)41(62)43(64)47(72-33)68-11-9-49(22-53)7-5-24(13-35(49)58)20-70-45(66)30-15-27-16-31(56)32(57)17-29(27)37(26-1-3-28(55)4-2-26)38(30)46(67)71-21-25-6-8-50(23-54,36(59)14-25)10-12-69-48-44(65)42(63)40(61)34(19-52)73-48/h1-4,9-12,15-17,22-25,33-44,47-48,51-52,55-65H,5-8,13-14,18-21H2/b11-9-,12-10-/t24-,25-,33+,34+,35-,36-,37+,38+,39+,40+,41-,42-,43+,44+,47+,48+,49+,50+/m0/s1
• InChI Key: WJXUWXFVYVROPE-FEXGQHPCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₆₂O₂₃
• Molecular Weight: 1031.00 g/mol
• Exact Mass: 1030.36818822 g/mol
• Topological Polar Surface Area (TPSA): 387.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.61
• H-Bond Acceptor: 23
• H-Bond Donor: 13
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6439	64.39%
Caco-2	-	0.8627	86.27%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7090	70.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8213	82.13%
OATP1B3 inhibitior	+	0.9392	93.92%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7596	75.96%
BSEP inhibitior	+	0.9380	93.80%
P-glycoprotein inhibitior	+	0.7403	74.03%
P-glycoprotein substrate	+	0.5583	55.83%
CYP3A4 substrate	+	0.7140	71.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8644	86.44%
CYP3A4 inhibition	-	0.9029	90.29%
CYP2C9 inhibition	-	0.8566	85.66%
CYP2C19 inhibition	-	0.7590	75.90%
CYP2D6 inhibition	-	0.8791	87.91%
CYP1A2 inhibition	-	0.7809	78.09%
CYP2C8 inhibition	+	0.8243	82.43%
CYP inhibitory promiscuity	-	0.9186	91.86%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6551	65.51%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.8991	89.91%
Skin irritation	-	0.7932	79.32%
Skin corrosion	-	0.9514	95.14%
Ames mutagenesis	-	0.5995	59.95%
Human Ether-a-go-go-Related Gene inhibition	+	0.7177	71.77%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8568	85.68%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7622	76.22%
Acute Oral Toxicity (c)	III	0.4113	41.13%
Estrogen receptor binding	+	0.7363	73.63%
Androgen receptor binding	+	0.7523	75.23%
Thyroid receptor binding	+	0.5980	59.80%
Glucocorticoid receptor binding	+	0.7174	71.74%
Aromatase binding	+	0.5580	55.80%
PPAR gamma	+	0.7891	78.91%
Honey bee toxicity	-	0.6636	66.36%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6455	64.55%
Fish aquatic toxicity	+	0.9680	96.80%

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	99.66%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.34%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	98.14%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.17%	95.93%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	93.49%	97.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	92.58%	97.28%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	92.22%	89.67%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	92.00%	94.23%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	91.98%	89.44%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.69%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.48%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.30%	89.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	88.21%	97.53%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.85%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.38%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.34%	100.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	86.12%	85.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.67%	95.78%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	85.59%	96.69%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.05%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.66%	86.92%
CHEMBL5255	O00206	Toll-like receptor 4	84.25%	92.50%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.95%	89.62%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.47%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.44%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.60%	86.33%
CHEMBL3194	P02766	Transthyretin	82.56%	90.71%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.18%	90.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.93%	92.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.01%	85.14%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.88%	94.62%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.78%	91.71%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.49%	94.80%

Plants that contains it

• Cananga odorata

Cross-Links

• PubChem: 90676278
• LOTUS: LTS0070047
• wikiData: Q105307125