[(2R,3S,4S,5R,6S)-6-[4-[(3S,3aR,6S,6aR)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

Details

• Internal ID: 500fda8f-9a58-4e2e-a853-5ad88bd768f3
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[4-[(3S,3aR,6S,6aR)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)OC5C(C(C(C(O5)COC(=O)C6=CC(=C(C(=C6)O)O)O)O)O)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)C6=CC(=C(C(=C6)O)O)O)O)O)O)OC)O
• InChI: InChI=1S/C33H36O15/c1-42-23-9-14(3-5-19(23)34)30-17-11-45-31(18(17)12-44-30)15-4-6-22(24(10-15)43-2)47-33-29(40)28(39)27(38)25(48-33)13-46-32(41)16-7-20(35)26(37)21(36)8-16/h3-10,17-18,25,27-31,33-40H,11-13H2,1-2H3/t17-,18-,25+,27+,28-,29+,30+,31+,33+/m0/s1
• InChI Key: CNAUBOMXRQZNJK-RPWTUCJISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₆O₁₅
• Molecular Weight: 672.60 g/mol
• Exact Mass: 672.20542044 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.64
• H-Bond Acceptor: 15
• 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	+	0.6796	67.96%
Caco-2	-	0.8754	87.54%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8084	80.84%
OATP2B1 inhibitior	-	0.5795	57.95%
OATP1B1 inhibitior	+	0.7615	76.15%
OATP1B3 inhibitior	+	0.9544	95.44%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6332	63.32%
P-glycoprotein inhibitior	+	0.6934	69.34%
P-glycoprotein substrate	-	0.6856	68.56%
CYP3A4 substrate	+	0.6440	64.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8403	84.03%
CYP3A4 inhibition	-	0.7525	75.25%
CYP2C9 inhibition	-	0.8150	81.50%
CYP2C19 inhibition	-	0.6197	61.97%
CYP2D6 inhibition	-	0.8939	89.39%
CYP1A2 inhibition	-	0.8641	86.41%
CYP2C8 inhibition	+	0.7652	76.52%
CYP inhibitory promiscuity	-	0.5285	52.85%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6268	62.68%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9019	90.19%
Skin irritation	-	0.8500	85.00%
Skin corrosion	-	0.9599	95.99%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8135	81.35%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8778	87.78%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.9833	98.33%
Acute Oral Toxicity (c)	III	0.6695	66.95%
Estrogen receptor binding	+	0.8039	80.39%
Androgen receptor binding	+	0.6947	69.47%
Thyroid receptor binding	+	0.5557	55.57%
Glucocorticoid receptor binding	+	0.7055	70.55%
Aromatase binding	+	0.5847	58.47%
PPAR gamma	+	0.6890	68.90%
Honey bee toxicity	-	0.8661	86.61%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9639	96.39%

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	99.04%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.57%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	94.87%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.47%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.99%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.33%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	91.85%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.26%	94.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.01%	83.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.76%	89.00%
CHEMBL2535	P11166	Glucose transporter	87.87%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.55%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.32%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.26%	96.00%
CHEMBL4208	P20618	Proteasome component C5	86.19%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.70%	92.62%
CHEMBL2581	P07339	Cathepsin D	85.19%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	84.19%	92.50%
CHEMBL3194	P02766	Transthyretin	83.90%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	83.66%	94.73%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.11%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.40%	95.89%
CHEMBL5028	O14672	ADAM10	80.00%	97.50%

Plants that contains it

• Bobgunnia madagascariensis
• Calodendrum capense
• Croton caudatus
• Elaeocarpus fuscoides
• Jacobaea adonidifolia
• Macaranga tanarius
• Meconopsis horridula
• Oxera splendida
• Stevia eupatoria
• Vitex pinnata

Cross-Links

• PubChem: 44470458
• NPASS: NPC50102
• LOTUS: LTS0206229
• wikiData: Q104965525