Podophyllotoxin glucoside

Details

• Internal ID: 0c1616d7-9170-4268-8caf-32e0f8416318
• Taxonomy: Lignans, neolignans and related compounds > Lignan lactones > Podophyllotoxins
• IUPAC Name: (5R,5aR,8aR,9R)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-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=CC5=C(C=C24)OCO5)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)[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/C28H32O13/c1-34-17-4-11(5-18(35-2)26(17)36-3)20-12-6-15-16(39-10-38-15)7-13(12)25(14-9-37-27(33)21(14)20)41-28-24(32)23(31)22(30)19(8-29)40-28/h4-7,14,19-25,28-32H,8-10H2,1-3H3/t14-,19+,20+,21-,22+,23-,24+,25-,28-/m0/s1
• InChI Key: NXVJTGLCCSFGAT-QNDDJFOYSA-N
• Popularity: 174 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₃
• Molecular Weight: 576.50 g/mol
• Exact Mass: 576.18429107 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.23
• H-Bond Acceptor: 13
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• Podophyllotoxin glucoside
• podophyllotoxin-4-o-glucoside
• 16481-54-2
• SP-G Iia
• Podophyllotoxin beta-D-glucoside
• Podophyllotoxin-beta-D-glucoside
• NSC 163024
• Podophyllotoxin, 3-beta-D-glucopyranoside
• Podophyllotoxin-beta-D-benzylidene glucoside
• 4,6-O-Benzylide-beta-D-glucopyranosidepodophyllotoxin
• (5R,5aR,8aR,9R)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• Podophyllotoxin, beta-D-glucopyranoside
• 9-(beta-D-glucopyranosyloxy)-5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one (5R-(5alpha,5abeta,8aalpha,9alpha))-
• PGB
• Podophyllotoxin, 4,6-O-benzylidene-beta-D-glucopyranoside
• Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 9-(beta-D-glucopyranosyloxy)-5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5R-(5alpha,5abeta,8aalpha,9alpha))-
• prostaglandins B
• C28H32O13
• C28-H32-O13
• Podophyllotoxin 4-glucoside
• CHEMBL503644
• SCHEMBL2825043
• Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-(.beta.-D-glucopyranosyloxy)-5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, [5R-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.)]-
• HY-N1977
• AKOS040762211
• LS-117910
• CS-0018297

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5948	59.48%
Caco-2	-	0.8159	81.59%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6138	61.38%
OATP2B1 inhibitior	-	0.8724	87.24%
OATP1B1 inhibitior	+	0.7922	79.22%
OATP1B3 inhibitior	+	0.9617	96.17%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8881	88.81%
P-glycoprotein inhibitior	-	0.6350	63.50%
P-glycoprotein substrate	-	0.6405	64.05%
CYP3A4 substrate	+	0.6896	68.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8556	85.56%
CYP3A4 inhibition	-	0.6952	69.52%
CYP2C9 inhibition	-	0.8203	82.03%
CYP2C19 inhibition	-	0.7727	77.27%
CYP2D6 inhibition	-	0.9178	91.78%
CYP1A2 inhibition	-	0.9313	93.13%
CYP2C8 inhibition	+	0.5102	51.02%
CYP inhibitory promiscuity	+	0.6031	60.31%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5937	59.37%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9548	95.48%
Skin irritation	-	0.8298	82.98%
Skin corrosion	-	0.9519	95.19%
Ames mutagenesis	-	0.7878	78.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.6896	68.96%
Micronuclear	+	0.6933	69.33%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8894	88.94%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.7666	76.66%
Acute Oral Toxicity (c)	III	0.7638	76.38%
Estrogen receptor binding	+	0.8605	86.05%
Androgen receptor binding	+	0.8063	80.63%
Thyroid receptor binding	+	0.5594	55.94%
Glucocorticoid receptor binding	+	0.6955	69.55%
Aromatase binding	-	0.6370	63.70%
PPAR gamma	+	0.6190	61.90%
Honey bee toxicity	-	0.6376	63.76%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.7723	77.23%

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	99.22%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.69%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.86%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.93%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	94.70%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.80%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.94%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.92%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.66%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.90%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.40%	96.77%
CHEMBL2581	P07339	Cathepsin D	88.19%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.81%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.10%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.53%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.50%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.41%	89.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.15%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	81.26%	94.73%

Plants that contains it

• Callitris drummondii
• Dimorphotheca sinuata
• Heptapleurum capitatum
• Libocedrus chevalieri
• Linum cariense
• Podophyllum hexandrum
• Podophyllum peltatum
• Roldana mexicana
• Smilax glabra

Cross-Links

• PubChem: 161177
• NPASS: NPC152424
• ChEMBL: CHEMBL503644
• LOTUS: LTS0198830
• wikiData: Q104391221