(5R)-5beta-(3,4,5-Trimethoxyphenyl)-9alpha-(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyloxy)-5,5abeta,6,8,8aalpha,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6-one

Details

• Internal ID: c246039f-9e15-44ad-9bc7-6398e7f98434
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones > Podophyllotoxins
• IUPAC Name: (5S,5aS,8aS,9R)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]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=CC5=C(C=C24)OCO5)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)[C@H]2[C@H]3[C@@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O
• InChI: InChI=1S/C34H42O18/c1-43-18-4-12(5-19(44-2)31(18)45-3)22-13-6-16-17(49-11-48-16)7-14(13)30(15-9-46-32(42)23(15)22)52-34-29(41)27(39)25(37)21(51-34)10-47-33-28(40)26(38)24(36)20(8-35)50-33/h4-7,15,20-30,33-41H,8-11H2,1-3H3/t15-,20-,21-,22-,23-,24-,25-,26+,27+,28-,29-,30-,33-,34+/m1/s1
• InChI Key: XHMZLRFGDPKVBR-ZFNYPWDNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₂O₁₈
• Molecular Weight: 738.70 g/mol
• Exact Mass: 738.23711449 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.94
• H-Bond Acceptor: 18
• H-Bond Donor: 7
• Rotatable Bonds: 10

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	-	0.8761	87.61%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6138	61.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7907	79.07%
OATP1B3 inhibitior	+	0.9617	96.17%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7614	76.14%
P-glycoprotein inhibitior	-	0.4853	48.53%
P-glycoprotein substrate	-	0.5539	55.39%
CYP3A4 substrate	+	0.6998	69.98%
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	+	0.5804	58.04%
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	-	0.9272	92.72%
Skin irritation	-	0.8298	82.98%
Skin corrosion	-	0.9519	95.19%
Ames mutagenesis	-	0.7378	73.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7743	77.43%
Micronuclear	+	0.6933	69.33%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8894	88.94%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.7948	79.48%
Acute Oral Toxicity (c)	III	0.7638	76.38%
Estrogen receptor binding	+	0.8621	86.21%
Androgen receptor binding	+	0.7749	77.49%
Thyroid receptor binding	+	0.5411	54.11%
Glucocorticoid receptor binding	+	0.6905	69.05%
Aromatase binding	-	0.4929	49.29%
PPAR gamma	+	0.6664	66.64%
Honey bee toxicity	-	0.6424	64.24%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
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
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.11%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.98%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.24%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.06%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.65%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.34%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.26%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.21%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.84%	96.77%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.07%	96.00%
CHEMBL2581	P07339	Cathepsin D	88.00%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.43%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.26%	94.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.52%	89.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.50%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	83.16%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.15%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.57%	96.61%
CHEMBL4040	P28482	MAP kinase ERK2	80.20%	83.82%

Plants that contains it

• Dimorphotheca sinuata
• Heptapleurum capitatum
• Podophyllum hexandrum
• Roldana mexicana

Cross-Links

• PubChem: 10533021
• NPASS: NPC40278
• LOTUS: LTS0082513
• wikiData: Q105328211