5-Methoxypodophyllotoxin

Details

• Internal ID: 96aef807-04b5-462c-896e-38ab96f9d39c
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones > Podophyllotoxins
• IUPAC Name: (5R,5aR,8aR,9R)-5-hydroxy-4-methoxy-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)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
• InChI: InChI=1S/C23H24O9/c1-26-13-5-10(6-14(27-2)20(13)28-3)16-11-7-15-21(32-9-31-15)22(29-4)18(11)19(24)12-8-30-23(25)17(12)16/h5-7,12,16-17,19,24H,8-9H2,1-4H3/t12-,16+,17-,19+/m0/s1
• InChI Key: PDQAOYGENRRPQO-UXDKQJBESA-N
• Popularity: 23 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₉
• Molecular Weight: 444.40 g/mol
• Exact Mass: 444.14203234 g/mol
• Topological Polar Surface Area (TPSA): 102.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.42
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 128443-52-7
• (5R-(5alpha,5abeta,8aalpha,9alpha))-5,8,8a,9-Tetrahydro-9-hydroxy-10-methoxy-5-(3,4,5-trimethoxyphenyl)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one
• (5R,5aR,8aR,9R)-5-hydroxy-4-methoxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• 6-methoxypodophyllotoxin
• 5-methoxy podophyllotoxin
• CHEMBL292945
• DTXSID00155903
• CHEBI:188507
• C23H24O9
• Q63398578
• (5R,5aR,8aR,9R)-5-hydroxy-4-methoxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzouro[6,5-][1,3]benzodioxol-8-one
• Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-10-methoxy-5-(3,4,5-trimethoxyphenyl)-, (5R-(5alpha,5abeta,8aalpha,9alpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9873	98.73%
Caco-2	+	0.6492	64.92%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7743	77.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8698	86.98%
OATP1B3 inhibitior	+	0.9603	96.03%
MATE1 inhibitior	+	0.6000	60.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9309	93.09%
P-glycoprotein inhibitior	-	0.4344	43.44%
P-glycoprotein substrate	-	0.8855	88.55%
CYP3A4 substrate	+	0.6208	62.08%
CYP2C9 substrate	-	0.6043	60.43%
CYP2D6 substrate	-	0.7886	78.86%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.8948	89.48%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.5817	58.17%
CYP inhibitory promiscuity	+	0.7468	74.68%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4302	43.02%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9301	93.01%
Skin irritation	-	0.8127	81.27%
Skin corrosion	-	0.9705	97.05%
Ames mutagenesis	-	0.6654	66.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4852	48.52%
Micronuclear	+	0.8674	86.74%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.7800	78.00%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.6734	67.34%
Acute Oral Toxicity (c)	III	0.5663	56.63%
Estrogen receptor binding	+	0.8719	87.19%
Androgen receptor binding	+	0.8016	80.16%
Thyroid receptor binding	+	0.8294	82.94%
Glucocorticoid receptor binding	+	0.8340	83.40%
Aromatase binding	-	0.7350	73.50%
PPAR gamma	-	0.4903	49.03%
Honey bee toxicity	-	0.6188	61.88%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9578	95.78%

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	96.98%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.93%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.02%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.06%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.03%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.24%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.41%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.59%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.27%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.59%	97.09%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	86.08%	82.67%
CHEMBL4040	P28482	MAP kinase ERK2	86.05%	83.82%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.70%	94.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.43%	89.62%
CHEMBL2535	P11166	Glucose transporter	85.01%	98.75%
CHEMBL2581	P07339	Cathepsin D	83.98%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.02%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.66%	97.14%

Plants that contains it

• Hernandia sonora
• Hugonia tomentosa
• Libocedrus chevalieri
• Linum album
• Linum capitatum
• Linum catharticum
• Linum flavum
• Linum mucronatum
• Linum nodiflorum
• Linum usitatissimum
• Linum viscosum

Cross-Links

• PubChem: 3035544
• NPASS: NPC207584
• ChEMBL: CHEMBL292945
• LOTUS: LTS0099667
• wikiData: Q63398578