(8R,8'R)-Secoisolariciresinol 9,9'-bis-[4-carboxy-3-hydroxy-3-methylbutanoyl-(->6)-glucoside]

Details

• Internal ID: ab12558f-72d8-4f83-b73d-3459d7abee15
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 5-[[6-[3-[[6-[(4-carboxy-3-hydroxy-3-methylbutanoyl)oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methyl]butoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
• SMILES (Canonical): CC(CC(=O)O)(CC(=O)OCC1C(C(C(C(O1)OCC(CC2=CC(=C(C=C2)O)OC)C(CC3=CC(=C(C=C3)O)OC)COC4C(C(C(C(O4)COC(=O)CC(C)(CC(=O)O)O)O)O)O)O)O)O)O
• SMILES (Isomeric): CC(CC(=O)O)(CC(=O)OCC1C(C(C(C(O1)OCC(CC2=CC(=C(C=C2)O)OC)C(CC3=CC(=C(C=C3)O)OC)COC4C(C(C(C(O4)COC(=O)CC(C)(CC(=O)O)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C44H62O24/c1-43(59,13-31(47)48)15-33(51)63-19-29-35(53)37(55)39(57)41(67-29)65-17-23(9-21-5-7-25(45)27(11-21)61-3)24(10-22-6-8-26(46)28(12-22)62-4)18-66-42-40(58)38(56)36(54)30(68-42)20-64-34(52)16-44(2,60)14-32(49)50/h5-8,11-12,23-24,29-30,35-42,45-46,53-60H,9-10,13-20H2,1-4H3,(H,47,48)(H,49,50)
• InChI Key: CGAGPGOQPRKZLJ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₂O₂₄
• Molecular Weight: 974.90 g/mol
• Exact Mass: 974.36310284 g/mol
• Topological Polar Surface Area (TPSA): 385.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -1.90
• H-Bond Acceptor: 22
• H-Bond Donor: 12
• Rotatable Bonds: 25

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7013	70.13%
Caco-2	-	0.8621	86.21%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6388	63.88%
OATP2B1 inhibitior	-	0.8670	86.70%
OATP1B1 inhibitior	+	0.8317	83.17%
OATP1B3 inhibitior	+	0.9141	91.41%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8611	86.11%
P-glycoprotein inhibitior	+	0.7425	74.25%
P-glycoprotein substrate	-	0.6521	65.21%
CYP3A4 substrate	+	0.6361	63.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8750	87.50%
CYP3A4 inhibition	-	0.8783	87.83%
CYP2C9 inhibition	-	0.9006	90.06%
CYP2C19 inhibition	-	0.9112	91.12%
CYP2D6 inhibition	-	0.9307	93.07%
CYP1A2 inhibition	-	0.8579	85.79%
CYP2C8 inhibition	+	0.6603	66.03%
CYP inhibitory promiscuity	-	0.9607	96.07%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6105	61.05%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9013	90.13%
Skin irritation	-	0.8592	85.92%
Skin corrosion	-	0.9514	95.14%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7168	71.68%
Micronuclear	-	0.5726	57.26%
Hepatotoxicity	-	0.6890	68.90%
skin sensitisation	-	0.8848	88.48%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.9442	94.42%
Acute Oral Toxicity (c)	III	0.7140	71.40%
Estrogen receptor binding	+	0.8065	80.65%
Androgen receptor binding	+	0.6489	64.89%
Thyroid receptor binding	+	0.5758	57.58%
Glucocorticoid receptor binding	+	0.6901	69.01%
Aromatase binding	+	0.5847	58.47%
PPAR gamma	+	0.7738	77.38%
Honey bee toxicity	-	0.7920	79.20%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5649	56.49%
Fish aquatic toxicity	+	0.9354	93.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.41%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.14%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.12%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.03%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.81%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.54%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.00%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.26%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.39%	95.56%
CHEMBL2535	P11166	Glucose transporter	86.86%	98.75%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.60%	85.31%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.02%	95.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.08%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.69%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.54%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.94%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.34%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.23%	92.62%
CHEMBL1255126	O15151	Protein Mdm4	80.01%	90.20%

Plants that contains it

• Linum usitatissimum

Cross-Links

• PubChem: 131752786
• LOTUS: LTS0224707
• wikiData: Q104957330