(5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

Details

• Internal ID: 15e7e5c8-2ad2-45f2-a97d-c0700dfdca92
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones > Podophyllotoxins
• IUPAC Name: 5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
• InChI: InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3
• InChI Key: YVCVYCSAAZQOJI-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₈
• Molecular Weight: 400.40 g/mol
• Exact Mass: 400.11581759 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.11
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 9-Hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
• NSC659374
• NSC659375
• 4'-O-demethylepipodophyllotoxin;4'-DMEP
• MLS006011462
• SCHEMBL2077082
• CHEMBL1514122
• DTXSID70859981
• CHEBI:182324
• YVCVYCSAAZQOJI-UHFFFAOYSA-N
• BCP18484
• BBL033815
• STL372993
• AKOS025248010
• NCGC00095300-01
• NCGC00095300-02
• 5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• PD056343
• SMR002520339
• VS-12291
• FT-0618332
• FT-0658938
• A825142
• A835156
• 4-Demethyl-Podophyllotoxin;4'-O-demethylpodophyllotoxin
• 16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0(3),?.0(1)(1),(1)?]hexadeca-1(9),2,7-trien-12-one
• 5-(4-hydroxy-3,5-dimethoxyphenyl)-9-hydroxy-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
• 5-hydroxy-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,3]benzodioxol-8-one
• 5-hydroxy-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one
• 5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzouro[5,6-][1,3]benzodioxol-8-one
• 5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,3]benzodioxol-8-one
• 9-(3,5-dimethoxy-4-oxidanyl-phenyl)-5-oxidanyl-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• 9-Hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
• NCGC00095300-04!5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9809	98.09%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8045	80.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.7737	77.37%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.5200	52.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8192	81.92%
P-glycoprotein inhibitior	-	0.5957	59.57%
P-glycoprotein substrate	-	0.7443	74.43%
CYP3A4 substrate	+	0.6100	61.00%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	-	0.7880	78.80%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.9233	92.33%
CYP2C19 inhibition	+	0.9051	90.51%
CYP2D6 inhibition	-	0.7512	75.12%
CYP1A2 inhibition	-	0.8690	86.90%
CYP2C8 inhibition	-	0.6912	69.12%
CYP inhibitory promiscuity	+	0.8147	81.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4699	46.99%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9124	91.24%
Skin irritation	-	0.7982	79.82%
Skin corrosion	-	0.9593	95.93%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7389	73.89%
Micronuclear	+	0.8874	88.74%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.7824	78.24%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7485	74.85%
Acute Oral Toxicity (c)	III	0.7055	70.55%
Estrogen receptor binding	+	0.8807	88.07%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.7895	78.95%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	+	0.6287	62.87%
Honey bee toxicity	-	0.7510	75.10%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9583	95.83%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	6309.6 nM; 6309.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	17782.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.03%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.71%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.97%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.33%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.70%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.36%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.75%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.89%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.80%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.68%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.72%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.00%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.52%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.40%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.89%	89.62%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.80%	82.67%

Plants that contains it

• Condea verticillata
• Murraya paniculata
• Podophyllum delavayi
• Podophyllum difforme
• Podophyllum hexandrum
• Podophyllum peltatum

Cross-Links

• PubChem: 500181
• NPASS: NPC268718
• ChEMBL: CHEMBL1514122
• LOTUS: LTS0102661
• wikiData: Q105365216