Hapalindole B
| Internal ID | 2aa16a4d-b0d9-4c5a-a183-c6b63320e3dc |
| Taxonomy | Organoheterocyclic compounds > Indoles and derivatives > Indoles > 3-alkylindoles |
| IUPAC Name | (2R,3R,4R,5R,7S)-5-chloro-4-ethenyl-3-isothiocyanato-4,8,8-trimethyl-14-azatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),9(16),10,12-tetraene |
| SMILES (Canonical) | CC1(C2CC(C(C(C2C3=CNC4=CC=CC1=C43)N=C=S)(C)C=C)Cl)C |
| SMILES (Isomeric) | C[C@@]1([C@@H](C[C@H]2[C@@H]([C@H]1N=C=S)C3=CNC4=CC=CC(=C43)C2(C)C)Cl)C=C |
| InChI | InChI=1S/C21H23ClN2S/c1-5-21(4)16(22)9-14-18(19(21)24-11-25)12-10-23-15-8-6-7-13(17(12)15)20(14,2)3/h5-8,10,14,16,18-19,23H,1,9H2,2-4H3/t14-,16+,18-,19+,21-/m0/s1 |
| InChI Key | HYTBZXQKYMTBRU-DJNKVENRSA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C21H23ClN2S |
| Molecular Weight | 370.90 g/mol |
| Exact Mass | 370.1270476 g/mol |
| Topological Polar Surface Area (TPSA) | 60.20 Ų |
| XlogP | 6.90 |
| Atomic LogP (AlogP) | 5.83 |
| H-Bond Acceptor | 2 |
| H-Bond Donor | 1 |
| Rotatable Bonds | 2 |
| Hapalidole B |
| (-)-Hapalindole B |
| MLS004797561 |
| SCHEMBL10575482 |
| DTXSID101335336 |
| 92219-96-0 |
| SMR003519686 |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9901 | 99.01% |
| Caco-2 | - | 0.5537 | 55.37% |
| Blood Brain Barrier | + | 0.7500 | 75.00% |
| Human oral bioavailability | - | 0.5571 | 55.71% |
| Subcellular localzation | Lysosomes | 0.7488 | 74.88% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8547 | 85.47% |
| OATP1B3 inhibitior | + | 0.9418 | 94.18% |
| MATE1 inhibitior | - | 0.9200 | 92.00% |
| OCT2 inhibitior | - | 0.7000 | 70.00% |
| BSEP inhibitior | + | 0.6009 | 60.09% |
| P-glycoprotein inhibitior | - | 0.6424 | 64.24% |
| P-glycoprotein substrate | - | 0.5576 | 55.76% |
| CYP3A4 substrate | + | 0.6827 | 68.27% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.7177 | 71.77% |
| CYP3A4 inhibition | + | 0.7072 | 70.72% |
| CYP2C9 inhibition | - | 0.5753 | 57.53% |
| CYP2C19 inhibition | + | 0.7392 | 73.92% |
| CYP2D6 inhibition | - | 0.8005 | 80.05% |
| CYP1A2 inhibition | + | 0.6347 | 63.47% |
| CYP2C8 inhibition | + | 0.7165 | 71.65% |
| CYP inhibitory promiscuity | + | 0.9413 | 94.13% |
| UGT catelyzed | - | 0.0000 | 0.00% |
| Carcinogenicity (binary) | - | 0.6400 | 64.00% |
| Carcinogenicity (trinary) | Non-required | 0.5492 | 54.92% |
| Eye corrosion | - | 0.9786 | 97.86% |
| Eye irritation | - | 0.9830 | 98.30% |
| Skin irritation | - | 0.6969 | 69.69% |
| Skin corrosion | - | 0.8955 | 89.55% |
| Ames mutagenesis | + | 0.6600 | 66.00% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.7651 | 76.51% |
| Micronuclear | + | 0.6400 | 64.00% |
| Hepatotoxicity | + | 0.5459 | 54.59% |
| skin sensitisation | - | 0.6473 | 64.73% |
| Respiratory toxicity | + | 0.7222 | 72.22% |
| Reproductive toxicity | + | 0.5778 | 57.78% |
| Mitochondrial toxicity | - | 0.5125 | 51.25% |
| Nephrotoxicity | + | 0.5471 | 54.71% |
| Acute Oral Toxicity (c) | III | 0.4451 | 44.51% |
| Estrogen receptor binding | + | 0.8272 | 82.72% |
| Androgen receptor binding | + | 0.6581 | 65.81% |
| Thyroid receptor binding | + | 0.7820 | 78.20% |
| Glucocorticoid receptor binding | + | 0.6694 | 66.94% |
| Aromatase binding | + | 0.6449 | 64.49% |
| PPAR gamma | + | 0.6753 | 67.53% |
| Honey bee toxicity | - | 0.6183 | 61.83% |
| Biodegradation | - | 0.7250 | 72.50% |
| Crustacea aquatic toxicity | + | 0.7700 | 77.00% |
| Fish aquatic toxicity | + | 1.0000 | 100.00% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| No proven targets yet! | |||||
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL240 | Q12809 | HERG | 99.62% | 89.76% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 97.27% | 91.11% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 96.91% | 94.45% |
| CHEMBL222 | P23975 | Norepinephrine transporter | 95.86% | 96.06% |
| CHEMBL228 | P31645 | Serotonin transporter | 94.10% | 95.51% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 93.64% | 96.09% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 91.11% | 97.09% |
| CHEMBL4224 | P49759 | Dual specificty protein kinase CLK1 | 89.83% | 85.30% |
| CHEMBL3227 | P41594 | Metabotropic glutamate receptor 5 | 89.60% | 96.42% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 89.08% | 95.56% |
| CHEMBL2035 | P08912 | Muscarinic acetylcholine receptor M5 | 88.87% | 94.62% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 88.56% | 97.25% |
| CHEMBL238 | Q01959 | Dopamine transporter | 87.87% | 95.88% |
| CHEMBL2996 | Q05655 | Protein kinase C delta | 87.55% | 97.79% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 85.75% | 95.89% |
| CHEMBL2095226 | P05556 | Integrin alpha-5/beta-1 | 85.30% | 96.39% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 84.38% | 100.00% |
| CHEMBL3492 | P49721 | Proteasome Macropain subunit | 84.37% | 90.24% |
| CHEMBL225 | P28335 | Serotonin 2c (5-HT2c) receptor | 82.63% | 89.62% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 82.25% | 86.33% |
| CHEMBL1821 | P08173 | Muscarinic acetylcholine receptor M4 | 81.93% | 94.08% |
| CHEMBL3310 | Q96DB2 | Histone deacetylase 11 | 81.47% | 88.56% |
| CHEMBL5028 | O14672 | ADAM10 | 80.77% | 97.50% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 14157128 |
| LOTUS | LTS0066007 |
| wikiData | Q105035463 |