Bergapten
| Internal ID | 99cc4cac-6c73-4547-bc33-c934cf54a63e |
| Taxonomy | Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens > 5-methoxypsoralens |
| IUPAC Name | 4-methoxyfuro[3,2-g]chromen-7-one |
| SMILES (Canonical) | COC1=C2C=CC(=O)OC2=CC3=C1C=CO3 |
| SMILES (Isomeric) | COC1=C2C=CC(=O)OC2=CC3=C1C=CO3 |
| InChI | InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3 |
| InChI Key | BGEBZHIAGXMEMV-UHFFFAOYSA-N |
| Popularity | 1,702 references in papers |
| Molecular Formula | C12H8O4 |
| Molecular Weight | 216.19 g/mol |
| Exact Mass | 216.04225873 g/mol |
| Topological Polar Surface Area (TPSA) | 48.70 Ų |
| XlogP | 2.30 |
| Atomic LogP (AlogP) | 2.55 |
| H-Bond Acceptor | 4 |
| H-Bond Donor | 0 |
| Rotatable Bonds | 1 |
| 5-Methoxypsoralen |
| 484-20-8 |
| bergaptene |
| Heraclin |
| Majudin |
| 4-Methoxy-7H-furo[3,2-g]chromen-7-one |
| BERGAPTAN |
| Psoraderm |
| 5-Mop |
| O-Methylbergaptol |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9932 | 99.32% |
| Caco-2 | + | 0.8192 | 81.92% |
| Blood Brain Barrier | + | 0.5250 | 52.50% |
| Human oral bioavailability | + | 0.6429 | 64.29% |
| Subcellular localzation | Mitochondria | 0.6414 | 64.14% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.9513 | 95.13% |
| OATP1B3 inhibitior | + | 0.9798 | 97.98% |
| MATE1 inhibitior | - | 0.9200 | 92.00% |
| OCT2 inhibitior | - | 0.9750 | 97.50% |
| BSEP inhibitior | - | 0.8338 | 83.38% |
| P-glycoprotein inhibitior | - | 0.8789 | 87.89% |
| P-glycoprotein substrate | - | 0.9248 | 92.48% |
| CYP3A4 substrate | - | 0.6072 | 60.72% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8151 | 81.51% |
| CYP3A4 inhibition | + | 0.7959 | 79.59% |
| CYP2C9 inhibition | + | 0.8257 | 82.57% |
| CYP2C19 inhibition | + | 0.9296 | 92.96% |
| CYP2D6 inhibition | + | 0.8931 | 89.31% |
| CYP1A2 inhibition | + | 0.9774 | 97.74% |
| CYP2C8 inhibition | - | 0.8222 | 82.22% |
| CYP inhibitory promiscuity | + | 0.7435 | 74.35% |
| UGT catelyzed | - | 0.0000 | 0.00% |
| Carcinogenicity (binary) | - | 0.9600 | 96.00% |
| Carcinogenicity (trinary) | Warning | 0.4707 | 47.07% |
| Eye corrosion | - | 0.8443 | 84.43% |
| Eye irritation | + | 0.6231 | 62.31% |
| Skin irritation | - | 0.5812 | 58.12% |
| Skin corrosion | - | 0.9811 | 98.11% |
| Ames mutagenesis | + | 0.6900 | 69.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5230 | 52.30% |
| Micronuclear | + | 0.8100 | 81.00% |
| Hepatotoxicity | + | 0.8698 | 86.98% |
| skin sensitisation | - | 0.8682 | 86.82% |
| Respiratory toxicity | - | 0.5778 | 57.78% |
| Reproductive toxicity | + | 0.8222 | 82.22% |
| Mitochondrial toxicity | + | 0.5250 | 52.50% |
| Nephrotoxicity | - | 0.8188 | 81.88% |
| Acute Oral Toxicity (c) | III | 0.5714 | 57.14% |
| Estrogen receptor binding | + | 0.8705 | 87.05% |
| Androgen receptor binding | + | 0.8400 | 84.00% |
| Thyroid receptor binding | - | 0.5000 | 50.00% |
| Glucocorticoid receptor binding | + | 0.6779 | 67.79% |
| Aromatase binding | + | 0.9208 | 92.08% |
| PPAR gamma | + | 0.6863 | 68.63% |
| Honey bee toxicity | - | 0.8490 | 84.90% |
| Biodegradation | - | 0.7500 | 75.00% |
| Crustacea aquatic toxicity | + | 0.5400 | 54.00% |
| Fish aquatic toxicity | + | 0.8808 | 88.08% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
39810.7 nM 39810.7 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL2231 | P04798 | Cytochrome P450 1A1 |
60 nM |
Ki |
via Super-PRED
|
| CHEMBL5282 | P11509 | Cytochrome P450 2A6 |
12000 nM |
Ki |
PMID: 16248836
|
| CHEMBL3622 | P33261 | Cytochrome P450 2C19 |
3162.3 nM |
Potency |
via CMAUP
|
| CHEMBL3397 | P11712 | Cytochrome P450 2C9 |
5011.9 nM |
Potency |
via CMAUP
|
| CHEMBL289 | P10635 | Cytochrome P450 2D6 |
1995.3 nM |
Potency |
via CMAUP
|
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
10000 nM 10000 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
39810.7 nM |
Potency |
via CMAUP
|
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
39810.7 nM |
Potency |
via CMAUP
|
| CHEMBL1951 | P21397 | Monoamine oxidase A |
13800 nM |
IC50 |
PMID: 23517722
|
| CHEMBL1963 | P16473 | Thyroid stimulating hormone receptor |
3981.1 nM 3981.1 nM |
Potency Potency |
via CMAUP
via CMAUP |
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL4306 | P22460 | Voltage-gated potassium channel subunit Kv1.5 | 97.16% | 94.03% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 96.50% | 91.11% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 91.61% | 95.56% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 91.05% | 94.45% |
| CHEMBL2581 | P07339 | Cathepsin D | 88.94% | 98.95% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 88.43% | 94.00% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 85.85% | 89.00% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 85.45% | 96.00% |
| CHEMBL5409 | Q8TDU6 | G-protein coupled bile acid receptor 1 | 83.06% | 93.65% |
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 | 2355 |
| NPASS | NPC74539 |
| ChEMBL | CHEMBL24171 |
| LOTUS | LTS0019861 |
| wikiData | Q414779 |