(5R,5aR,8aR,9R)-9-(3,4-dihydroxy-5-methoxyphenyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one

Details

• Internal ID: b9389710-f6f7-4410-b7ba-b5b1f8692019
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones > Podophyllotoxins
• IUPAC Name: (5R,5aR,8aR,9R)-9-(3,4-dihydroxy-5-methoxyphenyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)[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)O)O)O
• InChI: InChI=1S/C26H28O13/c1-34-16-3-9(2-13(28)20(16)29)18-10-4-14-15(37-8-36-14)5-11(10)24(12-7-35-25(33)19(12)18)39-26-23(32)22(31)21(30)17(6-27)38-26/h2-5,12,17-19,21-24,26-32H,6-8H2,1H3/t12-,17+,18+,19-,21+,22-,23+,24-,26-/m0/s1
• InChI Key: APMHKJVIAHKYMZ-BEFYGXHQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₃
• Molecular Weight: 548.50 g/mol
• Exact Mass: 548.15299094 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.37
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6191	61.91%
Caco-2	-	0.8921	89.21%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6374	63.74%
OATP2B1 inhibitior	-	0.8633	86.33%
OATP1B1 inhibitior	-	0.3601	36.01%
OATP1B3 inhibitior	+	0.9728	97.28%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7872	78.72%
P-glycoprotein inhibitior	-	0.7598	75.98%
P-glycoprotein substrate	+	0.6211	62.11%
CYP3A4 substrate	+	0.6984	69.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8552	85.52%
CYP3A4 inhibition	-	0.5836	58.36%
CYP2C9 inhibition	-	0.7784	77.84%
CYP2C19 inhibition	-	0.7015	70.15%
CYP2D6 inhibition	-	0.8616	86.16%
CYP1A2 inhibition	-	0.9048	90.48%
CYP2C8 inhibition	+	0.5550	55.50%
CYP inhibitory promiscuity	+	0.6208	62.08%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5596	55.96%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9406	94.06%
Skin irritation	-	0.8137	81.37%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	-	0.7678	76.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.6611	66.11%
Micronuclear	+	0.7033	70.33%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8847	88.47%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.7008	70.08%
Acute Oral Toxicity (c)	III	0.7562	75.62%
Estrogen receptor binding	+	0.8230	82.30%
Androgen receptor binding	+	0.7847	78.47%
Thyroid receptor binding	-	0.5151	51.51%
Glucocorticoid receptor binding	+	0.6132	61.32%
Aromatase binding	-	0.6508	65.08%
PPAR gamma	+	0.5870	58.70%
Honey bee toxicity	-	0.6822	68.22%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.7290	72.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.80%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.35%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.92%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.02%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.58%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.35%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.11%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.82%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.66%	94.00%
CHEMBL4040	P28482	MAP kinase ERK2	90.44%	83.82%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.87%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.86%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.94%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.54%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.36%	89.62%
CHEMBL3401	O75469	Pregnane X receptor	85.41%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.11%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.59%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.88%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.42%	95.89%

Plants that contains it

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

Cross-Links

• PubChem: 101242502
• NPASS: NPC236125