Picropodopyllotoxone

Details

• Internal ID: 3f57f20e-348a-4f9d-b0d6-40aa422055e0
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones
• IUPAC Name: (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxole-5,8-dione
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(=O)C4=CC5=C(C=C24)OCO5
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)[C@H]2[C@H]3[C@H](COC3=O)C(=O)C4=CC5=C(C=C24)OCO5
• InChI: InChI=1S/C22H20O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-19H,8-9H2,1-3H3/t13-,18+,19+/m0/s1
• InChI Key: ISCQYPPCSYRZOT-MJXNMMHHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₈
• Molecular Weight: 412.40 g/mol
• Exact Mass: 412.11581759 g/mol
• Topological Polar Surface Area (TPSA): 89.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• PICROPODOPHYLLONE
• 477-48-5
• Picropodopyllotoxon
• (-)-Picropodopyllone
• (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxole-5,8-dione
• 5a,6,8a,9-Tetrahydro-9-(3,4,5-trimethoxyphenyl)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxole-5,8-dione (5aR-(5aalpha,8aalpha,9aalpha))-
• Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxole-5,8-dione, 5a,6,8a,9-tetrahydro-9-(3,4,5-trimethoxyphenyl)-, (5aR-(5aalpha,8aalpha,9aalpha))-
• C22H20O8
• (5R)-5,8,8abeta,9-Tetrahydro-5beta-(3,4,5-trimethoxyphenyl)furo[3',4'
• CHEMBL82303
• SCHEMBL18381519
• DTXSID40197246
• HY-N7684
• AKOS040760634
• MS-27118
• CS-0135208

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9880	98.80%
Caco-2	+	0.8197	81.97%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8949	89.49%
OATP1B3 inhibitior	+	0.9637	96.37%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9032	90.32%
P-glycoprotein inhibitior	+	0.7120	71.20%
P-glycoprotein substrate	-	0.9046	90.46%
CYP3A4 substrate	+	0.6009	60.09%
CYP2C9 substrate	-	0.8095	80.95%
CYP2D6 substrate	-	0.8508	85.08%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	+	0.9168	91.68%
CYP2C19 inhibition	+	0.8720	87.20%
CYP2D6 inhibition	-	0.8513	85.13%
CYP1A2 inhibition	-	0.7873	78.73%
CYP2C8 inhibition	-	0.5705	57.05%
CYP inhibitory promiscuity	+	0.8669	86.69%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.4094	40.94%
Eye corrosion	-	0.9847	98.47%
Eye irritation	-	0.8732	87.32%
Skin irritation	-	0.8444	84.44%
Skin corrosion	-	0.9652	96.52%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4100	41.00%
Micronuclear	+	0.7874	78.74%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.6432	64.32%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.8152	81.52%
Acute Oral Toxicity (c)	III	0.6673	66.73%
Estrogen receptor binding	+	0.8973	89.73%
Androgen receptor binding	+	0.7927	79.27%
Thyroid receptor binding	+	0.7468	74.68%
Glucocorticoid receptor binding	+	0.9248	92.48%
Aromatase binding	-	0.7101	71.01%
PPAR gamma	+	0.6440	64.40%
Honey bee toxicity	-	0.6264	62.64%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9776	97.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.17%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.89%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.81%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.96%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.79%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.26%	95.56%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	92.08%	96.86%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.01%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.75%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.73%	89.62%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.97%	82.67%
CHEMBL2581	P07339	Cathepsin D	87.31%	98.95%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	86.41%	80.96%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.09%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.60%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.30%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.28%	94.45%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	83.91%	96.09%
CHEMBL2535	P11166	Glucose transporter	82.85%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.78%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.00%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.48%	96.00%

Plants that contains it

• Campsis grandiflora
• Chrysosplenium tetrandrum
• Dimorphotheca sinuata
• Galega officinalis
• Heptapleurum capitatum
• Juniperus sabina
• Panax notoginseng
• Podophyllum aurantiocaule
• Podophyllum hexandrum
• Podophyllum pleianthum
• Podophyllum sinense
• Podophyllum versipelle
• Roldana mexicana
• Tacca plantaginea

Cross-Links

• PubChem: 3083574
• NPASS: NPC209411
• ChEMBL: CHEMBL82303
• LOTUS: LTS0063075
• wikiData: Q83070175