(9R,13R)-5-hydroxy-3,4-dimethoxy-11,18,20-trioxapentacyclo[13.7.0.02,7.09,13.017,21]docosa-1(22),2,4,6,15,17(21)-hexaene-10,14-dione

Details

• Internal ID: 47e7c340-acf4-4b41-a3cd-0f7fbe9c2446
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones
• IUPAC Name: (9R,13R)-5-hydroxy-3,4-dimethoxy-11,18,20-trioxapentacyclo[13.7.0.02,7.09,13.017,21]docosa-1(22),2,4,6,15,17(21)-hexaene-10,14-dione
• SMILES (Canonical): COC1=C(C=C2CC3C(COC3=O)C(=O)C4=CC5=C(C=C4C2=C1OC)OCO5)O
• SMILES (Isomeric): COC1=C(C=C2C[C@@H]3[C@H](COC3=O)C(=O)C4=CC5=C(C=C4C2=C1OC)OCO5)O
• InChI: InChI=1S/C21H18O8/c1-25-19-14(22)4-9-3-12-13(7-27-21(12)24)18(23)11-6-16-15(28-8-29-16)5-10(11)17(9)20(19)26-2/h4-6,12-13,22H,3,7-8H2,1-2H3/t12-,13+/m1/s1
• InChI Key: WMYDPBCWNFPYSF-OLZOCXBDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₈
• Molecular Weight: 398.40 g/mol
• Exact Mass: 398.10016753 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.33
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9552	95.52%
Caco-2	+	0.6399	63.99%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8141	81.41%
OATP2B1 inhibitior	-	0.8666	86.66%
OATP1B1 inhibitior	+	0.8717	87.17%
OATP1B3 inhibitior	+	0.9504	95.04%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8505	85.05%
P-glycoprotein inhibitior	-	0.5157	51.57%
P-glycoprotein substrate	-	0.8302	83.02%
CYP3A4 substrate	+	0.6124	61.24%
CYP2C9 substrate	-	0.5966	59.66%
CYP2D6 substrate	-	0.7971	79.71%
CYP3A4 inhibition	+	0.8765	87.65%
CYP2C9 inhibition	+	0.8569	85.69%
CYP2C19 inhibition	+	0.8392	83.92%
CYP2D6 inhibition	-	0.6537	65.37%
CYP1A2 inhibition	-	0.5994	59.94%
CYP2C8 inhibition	-	0.6801	68.01%
CYP inhibitory promiscuity	+	0.6395	63.95%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.4914	49.14%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.8021	80.21%
Skin irritation	-	0.8206	82.06%
Skin corrosion	-	0.9631	96.31%
Ames mutagenesis	-	0.5654	56.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6328	63.28%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.6424	64.24%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5060	50.60%
Acute Oral Toxicity (c)	III	0.4253	42.53%
Estrogen receptor binding	+	0.8567	85.67%
Androgen receptor binding	+	0.6978	69.78%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.8394	83.94%
Aromatase binding	-	0.6339	63.39%
PPAR gamma	+	0.7654	76.54%
Honey bee toxicity	-	0.8495	84.95%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9899	98.99%

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	99.11%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.59%	96.77%
CHEMBL2581	P07339	Cathepsin D	96.43%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.39%	96.09%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	92.20%	80.96%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.98%	89.00%
CHEMBL2535	P11166	Glucose transporter	88.50%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.07%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.84%	92.62%
CHEMBL261	P00915	Carbonic anhydrase I	85.49%	96.76%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.06%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.01%	96.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.58%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.29%	96.21%
CHEMBL1951	P21397	Monoamine oxidase A	84.28%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.18%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.37%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.26%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.24%	94.80%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.12%	100.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	82.99%	82.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.96%	86.33%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.63%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.05%	99.17%

Plants that contains it

• Steganotaenia araliacea

Cross-Links

• PubChem: 44576293
• LOTUS: LTS0136038
• wikiData: Q105308917