Plumbagin
| Internal ID | 6f5ff01c-8e8f-4d96-819c-adf21539a2b9 |
| Taxonomy | Benzenoids > Naphthalenes > Naphthoquinones |
| IUPAC Name | 5-hydroxy-2-methylnaphthalene-1,4-dione |
| SMILES (Canonical) | CC1=CC(=O)C2=C(C1=O)C=CC=C2O |
| SMILES (Isomeric) | CC1=CC(=O)C2=C(C1=O)C=CC=C2O |
| InChI | InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3 |
| InChI Key | VCMMXZQDRFWYSE-UHFFFAOYSA-N |
| Popularity | 1,595 references in papers |
| Molecular Formula | C11H8O3 |
| Molecular Weight | 188.18 g/mol |
| Exact Mass | 188.047344113 g/mol |
| Topological Polar Surface Area (TPSA) | 54.40 Ų |
| XlogP | 2.30 |
| Atomic LogP (AlogP) | 1.72 |
| H-Bond Acceptor | 3 |
| H-Bond Donor | 1 |
| Rotatable Bonds | 0 |
| 481-42-5 |
| Plumbagine |
| 2-Methyljuglone |
| 5-Hydroxy-2-methyl-1,4-naphthoquinone |
| Plumbaein |
| 5-hydroxy-2-methylnaphthalene-1,4-dione |
| Plumbagone |
| 5-Hydroxy-2-methyl-1,4-naphthalenedione |
| 1,4-Naphthalenedione, 5-hydroxy-2-methyl- |
| 5-Hydroxy-2-methyl-[1,4]naphthoquinone |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 1.0000 | 100.00% |
| Caco-2 | + | 0.7146 | 71.46% |
| Blood Brain Barrier | - | 0.7250 | 72.50% |
| Human oral bioavailability | + | 0.8000 | 80.00% |
| Subcellular localzation | Mitochondria | 0.8798 | 87.98% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.9343 | 93.43% |
| OATP1B3 inhibitior | + | 0.9776 | 97.76% |
| MATE1 inhibitior | - | 0.8600 | 86.00% |
| OCT2 inhibitior | - | 1.0000 | 100.00% |
| BSEP inhibitior | - | 0.9370 | 93.70% |
| P-glycoprotein inhibitior | - | 0.9681 | 96.81% |
| P-glycoprotein substrate | - | 0.9362 | 93.62% |
| CYP3A4 substrate | - | 0.5681 | 56.81% |
| CYP2C9 substrate | - | 0.8093 | 80.93% |
| CYP2D6 substrate | - | 0.8659 | 86.59% |
| CYP3A4 inhibition | - | 0.8351 | 83.51% |
| CYP2C9 inhibition | + | 0.8504 | 85.04% |
| CYP2C19 inhibition | + | 0.5513 | 55.13% |
| CYP2D6 inhibition | - | 0.7826 | 78.26% |
| CYP1A2 inhibition | + | 0.9504 | 95.04% |
| CYP2C8 inhibition | - | 0.9375 | 93.75% |
| CYP inhibitory promiscuity | + | 0.7349 | 73.49% |
| UGT catelyzed | + | 0.8000 | 80.00% |
| Carcinogenicity (binary) | - | 0.7906 | 79.06% |
| Carcinogenicity (trinary) | Non-required | 0.4831 | 48.31% |
| Eye corrosion | - | 0.9783 | 97.83% |
| Eye irritation | + | 0.9889 | 98.89% |
| Skin irritation | + | 0.7111 | 71.11% |
| Skin corrosion | - | 0.9239 | 92.39% |
| Ames mutagenesis | + | 0.9300 | 93.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.8297 | 82.97% |
| Micronuclear | + | 0.6808 | 68.08% |
| Hepatotoxicity | + | 0.8750 | 87.50% |
| skin sensitisation | + | 0.7017 | 70.17% |
| Respiratory toxicity | - | 0.5333 | 53.33% |
| Reproductive toxicity | + | 0.6667 | 66.67% |
| Mitochondrial toxicity | + | 0.5875 | 58.75% |
| Nephrotoxicity | + | 0.7840 | 78.40% |
| Acute Oral Toxicity (c) | II | 0.7316 | 73.16% |
| Estrogen receptor binding | - | 0.6106 | 61.06% |
| Androgen receptor binding | + | 0.5201 | 52.01% |
| Thyroid receptor binding | - | 0.7610 | 76.10% |
| Glucocorticoid receptor binding | - | 0.6010 | 60.10% |
| Aromatase binding | - | 0.7563 | 75.63% |
| PPAR gamma | - | 0.7221 | 72.21% |
| Honey bee toxicity | - | 0.9553 | 95.53% |
| Biodegradation | - | 0.5250 | 52.50% |
| Crustacea aquatic toxicity | - | 0.6500 | 65.00% |
| Fish aquatic toxicity | + | 0.9911 | 99.11% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
25118.9 nM |
Potency |
via CMAUP
|
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
15848.9 nM 39810.7 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
3162.3 nM |
Potency |
via CMAUP
|
| CHEMBL1293236 | P46063 | ATP-dependent DNA helicase Q1 |
22387.2 nM |
Potency |
via CMAUP
|
| CHEMBL1293237 | P54132 | Bloom syndrome protein |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL4801 | P29466 | Caspase-1 |
12589.3 nM 31622.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3468 | P55210 | Caspase-7 |
19952.6 nM |
Potency |
via CMAUP
|
| CHEMBL4096 | P04637 | Cellular tumor antigen p53 |
794.3 nM 794.3 nM 6309.6 nM 3981.1 nM 10000 nM |
Potency Potency Potency Potency Potency |
via Super-PRED
via CMAUP via CMAUP via CMAUP via CMAUP |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
31622.8 nM 31622.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3587 | Q02750 | Dual specificity mitogen-activated protein kinase kinase 1 |
12589.3 nM |
Potency |
via CMAUP
|
| CHEMBL3775 | P30304 | Dual specificity phosphatase Cdc25A |
700 nM |
IC50 |
via Super-PRED
|
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
39810.7 nM 12589.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3784 | Q09472 | Histone acetyltransferase p300 |
2000 nM 2000 nM |
IC50 IC50 |
DOI: 10.1039/C1MD00199J
PMID: 26701186 |
| CHEMBL5500 | Q92831 | Histone acetyltransferase PCAF |
50000 nM |
IC50 |
PMID: 26701186
|
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
6309.6 nM 8912.5 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4040 | P28482 | MAP kinase ERK2 |
5623.4 nM 10000 nM 7079.5 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
3162.3 nM 562.3 nM 631 nM 2511.9 nM 562.3 nM 891.3 nM 2238.7 nM |
Potency Potency Potency Potency Potency Potency Potency |
via CMAUP
via Super-PRED via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP |
| CHEMBL1824 | P04626 | Receptor protein-tyrosine kinase erbB-2 |
30800 nM |
IC50 |
PMID: 24355130
|
| CHEMBL1293232 | Q16637 | Survival motor neuron protein |
28183.8 nM |
Potency |
via CMAUP
|
| CHEMBL6007 | O75762 | Transient receptor potential cation channel subfamily A member 1 |
460 nM |
EC50 |
via Super-PRED
|
| CHEMBL1075138 | Q9NUW8 | Tyrosyl-DNA phosphodiesterase 1 |
39810.7 nM |
Potency |
via CMAUP
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL2581 | P07339 | Cathepsin D | 97.89% | 98.95% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 97.40% | 95.56% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 90.92% | 91.49% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 90.50% | 99.23% |
| CHEMBL1937 | Q92769 | Histone deacetylase 2 | 89.34% | 94.75% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 88.58% | 94.73% |
| CHEMBL2378 | P30307 | Dual specificity phosphatase Cdc25C | 87.44% | 96.67% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 85.94% | 89.00% |
| CHEMBL1907600 | Q00535 | Cyclin-dependent kinase 5/CDK5 activator 1 | 85.01% | 93.03% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 84.43% | 99.15% |
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.
| PubChem | 10205 |
| NPASS | NPC285829 |
| ChEMBL | CHEMBL295316 |
| LOTUS | LTS0212929 |
| wikiData | Q2550553 |