Podofilox
Internal ID | b4dc8419-9204-4208-8137-46fdd2a39a81 |
Taxonomy | Lignans, neolignans and related compounds > Lignan lactones > Podophyllotoxins |
IUPAC Name | (5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one |
SMILES (Canonical) | COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)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 |
InChI | InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1 |
InChI Key | YJGVMLPVUAXIQN-XVVDYKMHSA-N |
Popularity | 5,165 references in papers |
Molecular Formula | C22H22O8 |
Molecular Weight | 414.40 g/mol |
Exact Mass | 414.13146766 g/mol |
Topological Polar Surface Area (TPSA) | 92.70 Ų |
XlogP | 2.00 |
Atomic LogP (AlogP) | 2.41 |
H-Bond Acceptor | 8 |
H-Bond Donor | 1 |
Rotatable Bonds | 4 |
Podofilox |
518-28-5 |
Condylox |
Condyline |
(-)-Podophyllotoxin |
Wartec |
Podophyllinic acid lactone |
Podophyllotoxin 7 |
Warticon |
Podofilox [USAN] |
There are more than 10 synonyms. If you wish to see them all click here. |
Target | Value | Probability (raw) | Probability (%) |
---|---|---|---|
Human Intestinal Absorption | + | 0.9873 | 98.73% |
Caco-2 | + | 0.6986 | 69.86% |
Blood Brain Barrier | - | 0.6000 | 60.00% |
Human oral bioavailability | - | 0.5143 | 51.43% |
Subcellular localzation | Mitochondria | 0.7743 | 77.43% |
OATP2B1 inhibitior | - | 1.0000 | 100.00% |
OATP1B1 inhibitior | + | 0.7428 | 74.28% |
OATP1B3 inhibitior | + | 0.9603 | 96.03% |
MATE1 inhibitior | + | 0.6000 | 60.00% |
OCT2 inhibitior | - | 0.9500 | 95.00% |
BSEP inhibitior | + | 0.8646 | 86.46% |
P-glycoprotein inhibitior | - | 0.4318 | 43.18% |
P-glycoprotein substrate | - | 0.9449 | 94.49% |
CYP3A4 substrate | + | 0.5939 | 59.39% |
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 | - | 0.6856 | 68.56% |
CYP inhibitory promiscuity | + | 0.7468 | 74.68% |
UGT catelyzed | + | 0.6000 | 60.00% |
Carcinogenicity (binary) | - | 0.9500 | 95.00% |
Carcinogenicity (trinary) | Non-required | 0.4302 | 43.02% |
Eye corrosion | - | 0.9886 | 98.86% |
Eye irritation | - | 0.9541 | 95.41% |
Skin irritation | - | 0.8127 | 81.27% |
Skin corrosion | - | 0.9705 | 97.05% |
Ames mutagenesis | - | 0.8200 | 82.00% |
Human Ether-a-go-go-Related Gene inhibition | - | 0.5567 | 55.67% |
Micronuclear | + | 0.8674 | 86.74% |
Hepatotoxicity | + | 0.5375 | 53.75% |
skin sensitisation | - | 0.7800 | 78.00% |
Respiratory toxicity | + | 0.7111 | 71.11% |
Reproductive toxicity | + | 0.7222 | 72.22% |
Mitochondrial toxicity | + | 0.6000 | 60.00% |
Nephrotoxicity | + | 0.7839 | 78.39% |
Acute Oral Toxicity (c) | III | 0.5663 | 56.63% |
Estrogen receptor binding | + | 0.8906 | 89.06% |
Androgen receptor binding | + | 0.8697 | 86.97% |
Thyroid receptor binding | + | 0.8462 | 84.62% |
Glucocorticoid receptor binding | + | 0.8610 | 86.10% |
Aromatase binding | - | 0.7966 | 79.66% |
PPAR gamma | + | 0.5637 | 56.37% |
Honey bee toxicity | - | 0.7128 | 71.28% |
Biodegradation | - | 0.8250 | 82.50% |
Crustacea aquatic toxicity | - | 0.6200 | 62.00% |
Fish aquatic toxicity | + | 0.9578 | 95.78% |
Proven Targets:
CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
---|---|---|---|---|---|
CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
19952.6 nM |
Potency |
via CMAUP
|
CHEMBL4096 | P04637 | Cellular tumor antigen p53 |
15.8 nM |
Potency |
via Super-PRED
|
CHEMBL3622 | P33261 | Cytochrome P450 2C19 |
5000 nM |
IC50 |
via CMAUP
|
CHEMBL3397 | P11712 | Cytochrome P450 2C9 |
4000 nM |
IC50 |
via CMAUP
|
CHEMBL340 | P08684 | Cytochrome P450 3A4 |
600 nM |
IC50 |
via CMAUP
|
CHEMBL1806 | P11388 | DNA topoisomerase II alpha |
486 nM |
Kd |
via Super-PRED
|
CHEMBL1293278 | O75496 | Geminin |
35.5 nM |
Potency |
via Super-PRED
|
CHEMBL2034 | P04150 | Glucocorticoid receptor |
14 nM 14 nM |
IC50 IC50 |
via Super-PRED
PMID: 19364854 |
CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha |
15.8 nM 15.8 nM 15.8 nM 2 nM |
Potency Potency Potency Potency |
via Super-PRED
via CMAUP via CMAUP via Super-PRED |
CHEMBL4040 | P28482 | MAP kinase ERK2 |
25.1 nM 79.4 nM |
Potency Potency |
via Super-PRED
via Super-PRED |
CHEMBL5162 | Q6W5P4 | Neuropeptide S receptor |
125.9 nM |
Potency |
via Super-PRED
|
CHEMBL1293277 | O15118 | Niemann-Pick C1 protein |
501.2 nM 501.2 nM |
Potency Potency |
via Super-PRED
via CMAUP |
CHEMBL1795094 | P51843 | Nuclear receptor subfamily 0 group B member 1 |
2145 nM |
IC50 |
via CMAUP
|
CHEMBL2362980 | Q06710 | Paired box protein Pax-8 |
<
260 nM |
AC50 |
via CMAUP
|
CHEMBL1293235 | P02545 | Prelamin-A/C |
14.1 nM 89.1 nM 3.2 nM 31.6 nM 28.2 nM 28.2 nM |
Potency Potency Potency Potency Potency Potency |
via Super-PRED
via Super-PRED via Super-PRED via CMAUP via CMAUP via Super-PRED |
CHEMBL1293294 | P51151 | Ras-related protein Rab-9A |
112.2 nM 112.2 nM |
Potency Potency |
via CMAUP
via Super-PRED |
CHEMBL2842 | P42345 | Serine/threonine-protein kinase mTOR |
14.7 nM |
Potency |
via Super-PRED
|
CHEMBL1293232 | Q16637 | Survival motor neuron protein |
446.7 nM 446.7 nM |
Potency Potency |
via CMAUP
via Super-PRED |
CHEMBL1293256 | P40225 | Thrombopoietin |
39.8 nM |
Potency |
via Super-PRED
|
Predicted Targets (via Super-PRED):
CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
---|---|---|---|---|
CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 96.19% | 96.09% |
CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 95.73% | 91.11% |
CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 94.64% | 94.45% |
CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 91.92% | 95.56% |
CHEMBL4303 | P08238 | Heat shock protein HSP 90-beta | 91.61% | 96.77% |
CHEMBL2373 | P21730 | C5a anaphylatoxin chemotactic receptor | 90.60% | 92.62% |
CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 87.48% | 86.33% |
CHEMBL3137262 | O60341 | LSD1/CoREST complex | 86.72% | 97.09% |
CHEMBL2581 | P07339 | Cathepsin D | 85.28% | 98.95% |
CHEMBL5311 | P37023 | Serine/threonine-protein kinase receptor R3 | 85.11% | 82.67% |
CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 83.84% | 94.00% |
CHEMBL4247 | Q9UM73 | ALK tyrosine kinase receptor | 81.80% | 96.86% |
CHEMBL2535 | P11166 | Glucose transporter | 81.69% | 98.75% |
CHEMBL1994 | P08235 | Mineralocorticoid receptor | 81.57% | 100.00% |
CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 80.67% | 99.17% |
CHEMBL4478 | Q00975 | Voltage-gated N-type calcium channel alpha-1B subunit | 80.41% | 97.14% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
To see more specific details click the taxa you are interested in.
To see more specific details click the taxa you are interested in.