(3S,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-one

Details

• Internal ID: 2132b469-dda7-4b28-9338-d05ed063c61e
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (3S,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-one
• SMILES (Canonical): COC1=C(C=CC(=C1)CC2COC(=O)C2(CC3=CC(=C(C=C3)O)OC)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C[C@@H]2COC(=O)[C@@]2(CC3=CC(=C(C=C3)O)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C26H32O12/c1-34-18-8-13(3-5-16(18)28)7-15-12-36-25(33)26(15,10-14-4-6-17(29)19(9-14)35-2)38-24-23(32)22(31)21(30)20(11-27)37-24/h3-6,8-9,15,20-24,27-32H,7,10-12H2,1-2H3/t15-,20-,21-,22+,23-,24+,26+/m1/s1
• InChI Key: YAVQULWQXQRTKS-QDYGYTTASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₂
• Molecular Weight: 536.50 g/mol
• Exact Mass: 536.18937645 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.37
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6692	66.92%
Caco-2	-	0.8557	85.57%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8079	80.79%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.8948	89.48%
OATP1B3 inhibitior	+	0.9555	95.55%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6512	65.12%
P-glycoprotein inhibitior	-	0.4568	45.68%
P-glycoprotein substrate	-	0.7283	72.83%
CYP3A4 substrate	+	0.6344	63.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8283	82.83%
CYP3A4 inhibition	-	0.8215	82.15%
CYP2C9 inhibition	-	0.8657	86.57%
CYP2C19 inhibition	-	0.7756	77.56%
CYP2D6 inhibition	-	0.9203	92.03%
CYP1A2 inhibition	-	0.8786	87.86%
CYP2C8 inhibition	+	0.5872	58.72%
CYP inhibitory promiscuity	-	0.7411	74.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6340	63.40%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9368	93.68%
Skin irritation	-	0.8518	85.18%
Skin corrosion	-	0.9577	95.77%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7686	76.86%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8498	84.98%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8103	81.03%
Acute Oral Toxicity (c)	III	0.6429	64.29%
Estrogen receptor binding	+	0.7970	79.70%
Androgen receptor binding	+	0.6488	64.88%
Thyroid receptor binding	+	0.5514	55.14%
Glucocorticoid receptor binding	+	0.6175	61.75%
Aromatase binding	-	0.4826	48.26%
PPAR gamma	-	0.4864	48.64%
Honey bee toxicity	-	0.8016	80.16%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9052	90.52%

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	99.37%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.87%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.64%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.33%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.24%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.86%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.19%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.53%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.95%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.28%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.25%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.06%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.35%	95.83%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.18%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.83%	86.92%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.92%	97.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.42%	97.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.30%	95.89%
CHEMBL4208	P20618	Proteasome component C5	80.28%	90.00%
CHEMBL4530	P00488	Coagulation factor XIII	80.23%	96.00%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.22%	97.50%

Plants that contains it

• Pulsatilla cernua

Cross-Links

• PubChem: 72948060
• NPASS: NPC38699
• ChEMBL: CHEMBL3098861
• LOTUS: LTS0040436
• wikiData: Q104989091