(2S,10S,11S,15R)-2,11,24-trihydroxy-10-[(E)-3-hydroxy-3-methylbut-1-enyl]-13-methyl-19-[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexacyclo[14.8.0.02,11.03,8.010,15.018,23]tetracosa-1(16),3,5,7,13,17,19,21,23-nonaen-9-one

Details

• Internal ID: d45fe1e1-e3b8-4e81-85bf-58cc4f0102e6
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2S,10S,11S,15R)-2,11,24-trihydroxy-10-[(E)-3-hydroxy-3-methylbut-1-enyl]-13-methyl-19-[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexacyclo[14.8.0.02,11.03,8.010,15.018,23]tetracosa-1(16),3,5,7,13,17,19,21,23-nonaen-9-one
• SMILES (Canonical): CC1=CC2C3=C(C(=C4C=CC=C(C4=C3)OC5C(C(C(C(O5)CO)O)O)O)O)C6(C7=CC=CC=C7C(=O)C2(C6(C1)O)C=CC(C)(C)O)O
• SMILES (Isomeric): CC1=C[C@@H]2C3=C(C(=C4C=CC=C(C4=C3)O[C@@H]5[C@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)O)[C@]6(C7=CC=CC=C7C(=O)[C@@]2([C@]6(C1)O)/C=C/C(C)(C)O)O
• InChI: InChI=1S/C36H38O11/c1-17-13-23-21-14-20-18(8-6-10-24(20)46-32-30(41)29(40)28(39)25(16-37)47-32)27(38)26(21)36(45)22-9-5-4-7-19(22)31(42)34(23,35(36,44)15-17)12-11-33(2,3)43/h4-14,23,25,28-30,32,37-41,43-45H,15-16H2,1-3H3/b12-11+/t23-,25-,28+,29+,30+,32+,34-,35+,36+/m1/s1
• InChI Key: PWLKCHHZPGZNQY-UKWJPHCJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₈O₁₁
• Molecular Weight: 646.70 g/mol
• Exact Mass: 646.24141202 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.65
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8761	87.61%
Caco-2	-	0.8631	86.31%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6515	65.15%
OATP2B1 inhibitior	-	0.5697	56.97%
OATP1B1 inhibitior	+	0.8270	82.70%
OATP1B3 inhibitior	+	0.9234	92.34%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9476	94.76%
P-glycoprotein inhibitior	+	0.6987	69.87%
P-glycoprotein substrate	+	0.5897	58.97%
CYP3A4 substrate	+	0.7523	75.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8468	84.68%
CYP3A4 inhibition	-	0.8549	85.49%
CYP2C9 inhibition	-	0.7076	70.76%
CYP2C19 inhibition	-	0.5960	59.60%
CYP2D6 inhibition	-	0.7896	78.96%
CYP1A2 inhibition	+	0.6513	65.13%
CYP2C8 inhibition	+	0.7320	73.20%
CYP inhibitory promiscuity	-	0.7025	70.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6638	66.38%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9079	90.79%
Skin irritation	-	0.7869	78.69%
Skin corrosion	-	0.9414	94.14%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7704	77.04%
Micronuclear	-	0.5826	58.26%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8014	80.14%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6204	62.04%
Acute Oral Toxicity (c)	III	0.6044	60.44%
Estrogen receptor binding	+	0.8227	82.27%
Androgen receptor binding	+	0.7142	71.42%
Thyroid receptor binding	+	0.6112	61.12%
Glucocorticoid receptor binding	+	0.6549	65.49%
Aromatase binding	+	0.6325	63.25%
PPAR gamma	+	0.7007	70.07%
Honey bee toxicity	-	0.6842	68.42%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9758	97.58%

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	99.74%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.44%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.68%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	97.21%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.17%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	93.67%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.34%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.75%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.51%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	91.52%	94.75%
CHEMBL3401	O75469	Pregnane X receptor	91.27%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.00%	97.25%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	88.78%	100.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	88.78%	80.78%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	87.96%	97.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.14%	97.09%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	84.78%	93.65%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.45%	99.17%
CHEMBL4581	P52732	Kinesin-like protein 1	84.36%	93.18%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.85%	93.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.71%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.56%	94.00%
CHEMBL4208	P20618	Proteasome component C5	83.22%	90.00%
CHEMBL2535	P11166	Glucose transporter	82.52%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.07%	89.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.81%	99.23%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.67%	97.36%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.04%	95.83%

Plants that contains it

• Firmiana simplex

Cross-Links

• PubChem: 163062115
• LOTUS: LTS0017571
• wikiData: Q105215891