Papaverine
| Internal ID | 6c5e8e06-3e90-4cfc-99e2-8a39e1d4bed0 |
| Taxonomy | Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines |
| IUPAC Name | 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline |
| SMILES (Canonical) | COC1=C(C=C(C=C1)CC2=NC=CC3=CC(=C(C=C32)OC)OC)OC |
| SMILES (Isomeric) | COC1=C(C=C(C=C1)CC2=NC=CC3=CC(=C(C=C32)OC)OC)OC |
| InChI | InChI=1S/C20H21NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-8,10-12H,9H2,1-4H3 |
| InChI Key | XQYZDYMELSJDRZ-UHFFFAOYSA-N |
| Popularity | 14,089 references in papers |
| Molecular Formula | C20H21NO4 |
| Molecular Weight | 339.40 g/mol |
| Exact Mass | 339.14705815 g/mol |
| Topological Polar Surface Area (TPSA) | 49.80 Ų |
| XlogP | 3.90 |
| Atomic LogP (AlogP) | 3.86 |
| H-Bond Acceptor | 5 |
| H-Bond Donor | 0 |
| Rotatable Bonds | 6 |
| Papaverin |
| 58-74-2 |
| Papanerine |
| Robaxapap |
| Papanerin |
| Cerespan |
| Pavabid |
| Papaverina |
| 1-(3,4-Dimethoxybenzyl)-6,7-dimethoxyisoquinoline |
| Pavatym |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9939 | 99.39% |
| Caco-2 | + | 0.9313 | 93.13% |
| Blood Brain Barrier | - | 0.8000 | 80.00% |
| Human oral bioavailability | + | 0.7286 | 72.86% |
| Subcellular localzation | Mitochondria | 0.4515 | 45.15% |
| OATP2B1 inhibitior | - | 0.8691 | 86.91% |
| OATP1B1 inhibitior | + | 0.9401 | 94.01% |
| OATP1B3 inhibitior | + | 0.9690 | 96.90% |
| MATE1 inhibitior | - | 0.9200 | 92.00% |
| OCT2 inhibitior | - | 0.8500 | 85.00% |
| BSEP inhibitior | + | 0.7082 | 70.82% |
| P-glycoprotein inhibitior | - | 0.6160 | 61.60% |
| P-glycoprotein substrate | + | 0.8147 | 81.47% |
| CYP3A4 substrate | - | 0.5759 | 57.59% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | + | 0.4934 | 49.34% |
| CYP3A4 inhibition | + | 0.7959 | 79.59% |
| CYP2C9 inhibition | - | 0.9071 | 90.71% |
| CYP2C19 inhibition | + | 0.7780 | 77.80% |
| CYP2D6 inhibition | + | 0.8448 | 84.48% |
| CYP1A2 inhibition | + | 0.9107 | 91.07% |
| CYP2C8 inhibition | + | 0.8724 | 87.24% |
| CYP inhibitory promiscuity | + | 0.8558 | 85.58% |
| UGT catelyzed | - | 0.0000 | 0.00% |
| Carcinogenicity (binary) | - | 0.9010 | 90.10% |
| Carcinogenicity (trinary) | Non-required | 0.6207 | 62.07% |
| Eye corrosion | - | 0.9891 | 98.91% |
| Eye irritation | - | 0.9541 | 95.41% |
| Skin irritation | - | 0.8204 | 82.04% |
| Skin corrosion | - | 0.9774 | 97.74% |
| Ames mutagenesis | + | 0.8900 | 89.00% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.8916 | 89.16% |
| Micronuclear | + | 0.6118 | 61.18% |
| Hepatotoxicity | + | 0.9000 | 90.00% |
| skin sensitisation | - | 0.9393 | 93.93% |
| Respiratory toxicity | + | 0.7667 | 76.67% |
| Reproductive toxicity | + | 0.6667 | 66.67% |
| Mitochondrial toxicity | + | 0.7375 | 73.75% |
| Nephrotoxicity | - | 0.8449 | 84.49% |
| Acute Oral Toxicity (c) | II | 0.7448 | 74.48% |
| Estrogen receptor binding | + | 0.9393 | 93.93% |
| Androgen receptor binding | + | 0.6829 | 68.29% |
| Thyroid receptor binding | + | 0.8636 | 86.36% |
| Glucocorticoid receptor binding | + | 0.8727 | 87.27% |
| Aromatase binding | + | 0.6187 | 61.87% |
| PPAR gamma | + | 0.6118 | 61.18% |
| Honey bee toxicity | - | 0.8568 | 85.68% |
| Biodegradation | - | 0.9250 | 92.50% |
| Crustacea aquatic toxicity | + | 0.6800 | 68.00% |
| Fish aquatic toxicity | - | 0.5706 | 57.06% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL220 | P22303 | Acetylcholinesterase |
24330 nM |
IC50 |
PMID: 16483771
|
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
3548.1 nM |
Potency |
via CMAUP
|
| CHEMBL3687 | P18054 | Arachidonate 12-lipoxygenase |
7079.5 nM |
Potency |
via CMAUP
|
| CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
39810.7 nM |
Potency |
via CMAUP
|
| CHEMBL5747 | Q92793 | CREB-binding protein |
1258.9 nM 1258.9 nM 562.3 nM 7943.3 nM 7943.3 nM 10000 nM 707.9 nM 562.3 nM |
Potency Potency Potency Potency Potency Potency Potency Potency |
via CMAUP
via CMAUP via Super-PRED via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP |
| CHEMBL3356 | P05177 | Cytochrome P450 1A2 |
25118.86 nM 10000 nM |
AC50 AC50 |
via CMAUP
via CMAUP |
| CHEMBL3622 | P33261 | Cytochrome P450 2C19 |
762 nM |
IC50 |
via CMAUP
|
| CHEMBL3397 | P11712 | Cytochrome P450 2C9 |
39810.7 nM 12589.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL289 | P10635 | Cytochrome P450 2D6 |
10000 nM 12589.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
2511.9 nM 1995.3 nM 2511.9 nM 1995.3 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL240 | Q12809 | HERG |
7244.36 nM |
IC50 |
PMID: 21185626
|
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha |
2511.9 nM 10000 nM 10000 nM 2511.9 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL4040 | P28482 | MAP kinase ERK2 |
31622.8 nM 7943.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit |
10000 nM 10000 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4409 | Q9Y233 | Phosphodiesterase 10A |
17 nM 76 nM 21 nM 92.3 nM 36 nM 17 nM 36 nM 40 nM 36 nM 56.9 nM |
IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 |
PMID: 21087867
PMID: 20450197 PMID: 21705115 DOI: 10.1039/C5MD00419E PMID: 25592707 via Super-PRED PMID: 22321214 PMID: 22834877 PMID: 24721831 PMID: 20450197 |
| CHEMBL2652 | O00408 | Phosphodiesterase 2A |
17000 nM 2300 nM |
IC50 IC50 |
PMID: 2985781
PMID: 8254606 |
| CHEMBL241 | Q14432 | Phosphodiesterase 3A |
284 nM 279 nM 917 nM |
IC50 Ki IC50 |
PMID: 22834877
via Super-PRED PMID: 21705115 |
| CHEMBL290 | Q13370 | Phosphodiesterase 3B |
1030 nM 417 nM |
IC50 Ki |
PMID: 21705115
via Super-PRED |
| CHEMBL1827 | O76074 | Phosphodiesterase 5A |
8800 nM |
IC50 |
PMID: 8254606
|
| CHEMBL1293235 | P02545 | Prelamin-A/C |
1995.3 nM |
Potency |
via CMAUP
|
| CHEMBL1293232 | Q16637 | Survival motor neuron protein |
7943.3 nM |
Potency |
via CMAUP
|
| CHEMBL1293256 | P40225 | Thrombopoietin |
12589.3 nM 12589.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1963 | P16473 | Thyroid stimulating hormone receptor |
5011.9 nM 3162.3 nM 5011.9 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL1293227 | O75604 | Ubiquitin carboxyl-terminal hydrolase 2 |
12589.3 nM |
Potency |
via CMAUP
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 93.70% | 96.09% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 92.71% | 95.50% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 92.61% | 94.00% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 92.43% | 86.33% |
| CHEMBL2535 | P11166 | Glucose transporter | 91.22% | 98.75% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 89.72% | 99.17% |
| CHEMBL1255126 | O15151 | Protein Mdm4 | 89.70% | 90.20% |
| CHEMBL5925 | P22413 | Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 | 89.45% | 92.38% |
| CHEMBL4306 | P22460 | Voltage-gated potassium channel subunit Kv1.5 | 88.34% | 94.03% |
| CHEMBL235 | P37231 | Peroxisome proliferator-activated receptor gamma | 87.88% | 95.39% |
| CHEMBL225 | P28335 | Serotonin 2c (5-HT2c) receptor | 87.14% | 89.62% |
| CHEMBL2581 | P07339 | Cathepsin D | 85.53% | 98.95% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 84.28% | 96.00% |
| CHEMBL2373 | P21730 | C5a anaphylatoxin chemotactic receptor | 84.21% | 92.62% |
| CHEMBL1741221 | Q9Y4P1 | Cysteine protease ATG4B | 83.72% | 87.50% |
| CHEMBL4145 | Q9UKV0 | Histone deacetylase 9 | 83.50% | 85.49% |
| CHEMBL2243 | O00519 | Anandamide amidohydrolase | 82.30% | 97.53% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 81.79% | 94.45% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 80.16% | 95.89% |
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.
| Aloe microstigma |
| Breynia androgyna |
| Chrozophora plicata |
| Panax quinquefolius |
| Papaver somniferum |
| Papaver somniferum subsp. setigerum |
| Rauvolfia serpentina |
| PubChem | 4680 |
| NPASS | NPC195268 |
| ChEMBL | CHEMBL19224 |
| LOTUS | LTS0095724 |
| wikiData | Q410374 |