Epipodophyllotoxin acetate

Details

• Internal ID: aad92a17-331f-4e36-bc3b-754e1eb39c17
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones > Podophyllotoxins
• IUPAC Name: [(5S,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] acetate
• SMILES (Canonical): CC(=O)OC1C2COC(=O)C2C(C3=CC4=C(C=C13)OCO4)C5=CC(=C(C(=C5)OC)OC)OC
• SMILES (Isomeric): CC(=O)O[C@H]1[C@H]2COC(=O)[C@@H]2[C@@H](C3=CC4=C(C=C13)OCO4)C5=CC(=C(C(=C5)OC)OC)OC
• InChI: InChI=1S/C24H24O9/c1-11(25)33-22-14-8-17-16(31-10-32-17)7-13(14)20(21-15(22)9-30-24(21)26)12-5-18(27-2)23(29-4)19(6-12)28-3/h5-8,15,20-22H,9-10H2,1-4H3/t15-,20+,21-,22+/m0/s1
• InChI Key: SASVNKPCTLROPQ-QWIYEXKTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₄O₉
• Molecular Weight: 456.40 g/mol
• Exact Mass: 456.14203234 g/mol
• Topological Polar Surface Area (TPSA): 98.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.98
• H-Bond Acceptor: 9
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• epipodophyllotoxin acetate
• 1180-35-4
• [(5S,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] acetate
• 4-O-Epipodophyllotoxinyl acetate
• DTXSID901019938
• HY-N2812
• AKOS032962448
• FS-10195
• CS-0023367

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9880	98.80%
Caco-2	+	0.5829	58.29%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8568	85.68%
OATP1B3 inhibitior	+	0.9637	96.37%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9695	96.95%
P-glycoprotein inhibitior	+	0.8185	81.85%
P-glycoprotein substrate	-	0.8790	87.90%
CYP3A4 substrate	+	0.6482	64.82%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8437	84.37%
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	+	0.4806	48.06%
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	-	0.9030	90.30%
Skin irritation	-	0.8444	84.44%
Skin corrosion	-	0.9652	96.52%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6939	69.39%
Micronuclear	+	0.7874	78.74%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.6432	64.32%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.8475	84.75%
Acute Oral Toxicity (c)	III	0.6673	66.73%
Estrogen receptor binding	+	0.8411	84.11%
Androgen receptor binding	+	0.8302	83.02%
Thyroid receptor binding	+	0.7180	71.80%
Glucocorticoid receptor binding	+	0.9125	91.25%
Aromatase binding	-	0.6712	67.12%
PPAR gamma	+	0.5676	56.76%
Honey bee toxicity	-	0.6111	61.11%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9776	97.76%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	56.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.94%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.91%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.30%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.24%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.36%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	91.81%	83.82%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.30%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.74%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.44%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.13%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.55%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	84.90%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.33%	95.89%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.24%	89.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.14%	97.09%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	82.98%	80.96%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.87%	94.00%
CHEMBL2581	P07339	Cathepsin D	81.85%	98.95%
CHEMBL2535	P11166	Glucose transporter	81.35%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.84%	100.00%

Plants that contains it

• Juniperus sabina

Cross-Links

• PubChem: 14160030
• LOTUS: LTS0130782
• wikiData: Q105249109