(5R,5aR,8aR,9R)-4-methoxy-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one

Details

• Internal ID: 9f8476ae-1b32-44ba-a35f-372943acf144
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones > Podophyllotoxins
• IUPAC Name: (5R,5aR,8aR,9R)-4-methoxy-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=C(C5=C(C=C24)OCO5)OC)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](C4=C(C5=C(C=C24)OCO5)OC)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C29H34O14/c1-35-14-5-11(6-15(36-2)25(14)37-3)18-12-7-16-26(41-10-40-16)27(38-4)20(12)24(13-9-39-28(34)19(13)18)43-29-23(33)22(32)21(31)17(8-30)42-29/h5-7,13,17-19,21-24,29-33H,8-10H2,1-4H3/t13-,17+,18+,19-,21+,22-,23+,24+,29-/m0/s1
• InChI Key: ZBHUQQHYXHVILV-OVXQXXFISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₄
• Molecular Weight: 606.60 g/mol
• Exact Mass: 606.19485575 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.24
• H-Bond Acceptor: 14
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5948	59.48%
Caco-2	-	0.8223	82.23%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6138	61.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8467	84.67%
OATP1B3 inhibitior	+	0.9617	96.17%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9240	92.40%
P-glycoprotein inhibitior	-	0.5411	54.11%
P-glycoprotein substrate	-	0.6088	60.88%
CYP3A4 substrate	+	0.6873	68.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8556	85.56%
CYP3A4 inhibition	-	0.6952	69.52%
CYP2C9 inhibition	-	0.8203	82.03%
CYP2C19 inhibition	-	0.7727	77.27%
CYP2D6 inhibition	-	0.9178	91.78%
CYP1A2 inhibition	-	0.9313	93.13%
CYP2C8 inhibition	+	0.5779	57.79%
CYP inhibitory promiscuity	+	0.6031	60.31%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5937	59.37%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9418	94.18%
Skin irritation	-	0.8298	82.98%
Skin corrosion	-	0.9519	95.19%
Ames mutagenesis	-	0.6232	62.32%
Human Ether-a-go-go-Related Gene inhibition	+	0.7212	72.12%
Micronuclear	+	0.6933	69.33%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8894	88.94%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6041	60.41%
Acute Oral Toxicity (c)	III	0.7638	76.38%
Estrogen receptor binding	+	0.8474	84.74%
Androgen receptor binding	+	0.7664	76.64%
Thyroid receptor binding	+	0.5406	54.06%
Glucocorticoid receptor binding	+	0.6841	68.41%
Aromatase binding	-	0.5889	58.89%
PPAR gamma	+	0.5785	57.85%
Honey bee toxicity	-	0.5820	58.20%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.7723	77.23%

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	98.55%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.50%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.20%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.78%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.80%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.61%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.29%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.26%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.09%	96.77%
CHEMBL4040	P28482	MAP kinase ERK2	88.71%	83.82%
CHEMBL2581	P07339	Cathepsin D	87.92%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.87%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.86%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.49%	96.61%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.47%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.71%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.96%	89.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.68%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.95%	100.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.49%	82.67%

Plants that contains it

• Libocedrus chevalieri
• Linum cariense
• Linum catharticum
• Linum flavum

Cross-Links

• PubChem: 14229357
• LOTUS: LTS0044191
• wikiData: Q105370607