Benzyl isothiocyanate
AlkaPlorer ID: AK008337
Synonym: (Isothiocyanatomethyl)benzene, Phenylmethyl isothiocyanate, Benzyl mustard oil, Tromocaps, Tromalyt active substance, Urogran, FEMA 4428
IUPAC Name: isothiocyanatomethylbenzene
Structure
SMILES: S=C=NCC1=CC=CC=C1
InChI: InChI=1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2
InChIKey: MDKCFLQDBWCQCV-UHFFFAOYSA-N
Reference
Investigation of the Tuber Constituents of Maca (<i>Lepidium meyenii</i>Walp.)
PubChem CID: 2346
CAS: 58019-05-9
LOTUS: LTS0228692
SuperNatural Ⅲ: SN0222606
NPASS: NPC299134
COCONUT: CNP0122123
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|
Properties Information
Molecule Weight: 149.218
TPSA？: 12.36
MolLogP？: 2.2894000000000005
Number of H-Donors: 0
Number of H-Acceptors: 2
RingCount: 1
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Escherichia coli | GroEL/GroES | Inhibition | 75.0 | % | 10.1016/j.bmcl.2019.02.028 |
| Escherichia coli | GroEL/GroES | Inhibition | 82.0 | % | 10.1016/j.bmcl.2019.02.028 |
| Homo sapiens | 15-hydroxyprostaglandin dehydrogenase [NAD+] | Potency | 31622.8 | nM | None |
| Homo sapiens | 786-0 | GI50 | 421.7 | nM | None |
| Homo sapiens | A498 | GI50 | 4130.48 | nM | None |
| Homo sapiens | A549 | GI50 | 4487.45 | nM | None |
| Homo sapiens | A549 | IC50 | 20500.0 | nM | 10.1016/j.bmcl.2011.05.113 |
| Homo sapiens | ACHN | GI50 | 3990.25 | nM | None |
| Homo sapiens | Aldehyde dehydrogenase 1A1 | Potency | 2818.4 | nM | None |
| Homo sapiens | BT-549 | GI50 | 2322.74 | nM | None |
| Homo sapiens | Caco-2 | IC50 | 15000.0 | nM | 10.1021/jm800993r |
| Homo sapiens | CAKI-1 | GI50 | 1849.27 | nM | None |
| Homo sapiens | Cathepsin B | Activity | 18.0 | % | 10.1016/j.ejmech.2018.10.010 |
| Homo sapiens | Cathepsin B | Activity | 75.0 | % | 10.1016/j.ejmech.2018.10.010 |
| Homo sapiens | CCRF-CEM | GI50 | 453.94 | nM | None |
| Homo sapiens | Cellular tumor antigen p53 | Activity | nan | None | 10.1021/jm101199t |
| Homo sapiens | COLO 205 | GI50 | 1513.56 | nM | None |
| Homo sapiens | Cytochrome P450 3A4 | Potency | 25118.9 | nM | None |
| Homo sapiens | DU-145 | GI50 | 4130.48 | nM | None |
| Homo sapiens | EKVX | GI50 | 14588.14 | nM | None |
| Homo sapiens | Fructose-1,6-bisphosphatase | Inhibition | 4.1 | % | 10.1016/j.ejmech.2019.111749 |
| Homo sapiens | Glutathione S-transferase kappa 1 | Activity | 0.3 | uM min-1 (mg of protein)-1 | 10.1021/jm00079a025 |
| Homo sapiens | Glutathione S-transferase kappa 1 | Activity | 0.36 | uM min-1 (mg of protein)-1 | 10.1021/jm00079a025 |
| Homo sapiens | Glutathione S-transferase kappa 1 | Activity | 1.01 | uM min-1 (mg of protein)-1 | 10.1021/jm00079a025 |
| Homo sapiens | Glutathione S-transferase kappa 1 | Activity | 1.17 | uM min-1 (mg of protein)-1 | 10.1021/jm00079a025 |
| Homo sapiens | Glutathione S-transferase kappa 1 | Activity | 1.59 | uM min-1 (mg of protein)-1 | 10.1021/jm00079a025 |
| Homo sapiens | Glutathione S-transferase kappa 1 | Activity | 5.3 | uM min-1 (mg of protein)-1 | 10.1021/jm00079a025 |
| Homo sapiens | HCC 2998 | GI50 | 8279.42 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 603.95 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 3357.38 | nM | None |
| Homo sapiens | HepG2 | Activity | nan | None | 10.1016/j.bmcl.2010.01.044 |
| Homo sapiens | HL-60 | GI50 | 1857.8 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 3047.89 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 5767.66 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 7079.46 | nM | None |
| Homo sapiens | HT-1080 | IC50 | 50000.0 | nM | 10.1021/jm800993r |
| Homo sapiens | HT-29 | GI50 | 2471.72 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 2506.11 | nM | None |
| Homo sapiens | K562 | GI50 | 696.63 | nM | None |
| Homo sapiens | KM12 | GI50 | 895.36 | nM | None |
| Homo sapiens | LoVo | Activity | 17.8 | % | 10.1016/j.ejmech.2017.03.028 |
| Homo sapiens | LoVo | Activity | 67.6 | % | 10.1016/j.ejmech.2017.03.028 |
| Homo sapiens | LoVo | Activity | nan | None | 10.1016/j.ejmech.2017.03.028 |
| Homo sapiens | LoVo | FC | 11.0 | None | 10.1016/j.ejmech.2017.03.028 |
| Homo sapiens | LoVo | IC50 | 10500.0 | nM | 10.1016/j.bmcl.2011.05.113 |
| Homo sapiens | LoVo | IC50 | 12300.0 | nM | 10.1016/j.bmcl.2011.05.113 |
| Homo sapiens | LoVo | IC50 | 14500.0 | nM | 10.1016/j.bmcl.2015.11.045 |
| Homo sapiens | LoVo | IC50 | 14500.0 | nM | 10.1016/j.bmcl.2018.06.042 |
| Homo sapiens | LoVo | IC50 | 14500.0 | nM | 10.1016/j.ejmech.2017.03.028 |
| Homo sapiens | LOX IMVI | GI50 | 796.16 | nM | None |
| Homo sapiens | M14 | GI50 | 1674.94 | nM | None |
| Homo sapiens | Macrophage migration inhibitory factor | IC50 | 530.0 | nM | 10.1016/j.ejmech.2015.02.012 |
| Homo sapiens | Macrophage migration inhibitory factor | IC50 | 540.0 | nM | 10.1016/j.ejmech.2015.02.012 |
| Homo sapiens | Macrophage migration inhibitory factor | IC50 | 790.0 | nM | 10.1021/acs.jmedchem.8b00589 |
| Homo sapiens | Macrophage migration inhibitory factor | Kd | 2900.0 | nM | 10.1021/acs.jmedchem.0c01160 |
| Homo sapiens | Macrophage migration inhibitory factor | Ki | 4300.0 | nM | 10.1021/acs.jmedchem.0c01160 |
| Homo sapiens | Malme-3M | GI50 | 3097.42 | nM | None |
| Homo sapiens | MCF7 | GI50 | 3228.49 | nM | None |
| Homo sapiens | MCF7 | IC50 | 18900.0 | nM | 10.1016/j.bmcl.2011.05.113 |
| Homo sapiens | MDA-MB-231 | Activity | nan | None | 10.1021/jm101199t |
| Homo sapiens | MDA-MB-231 | GI50 | 1798.87 | nM | None |
| Homo sapiens | MDA-MB-231 | IC50 | 42000.0 | nM | 10.1021/jm800993r |
| Homo sapiens | MDA-MB-435 | GI50 | 2162.72 | nM | None |
| Homo sapiens | MDA-N | GI50 | 1177.61 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 1312.2 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 3427.68 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 10115.79 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 3810.66 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 13931.57 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 6266.14 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 1221.8 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 2747.89 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 3801.89 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 10939.56 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 2618.18 | nM | None |
| Homo sapiens | PC-3 | GI50 | 4102.04 | nM | None |
| Homo sapiens | PC-3 | IC50 | 50000.0 | nM | 10.1021/jm800993r |
| Homo sapiens | P-glycoprotein 1 | Activity | 2.5 | fold | 10.1023/a:1020460700877 |
| Homo sapiens | P-glycoprotein 1 | Activity | nan | None | 10.1002/jps.20101 |
| Homo sapiens | Probable ubiquitin carboxyl-terminal hydrolase FAF-X | K | 170.0 | /M/s | 10.1016/j.bmcl.2018.11.055 |
| Homo sapiens | Protein-tyrosine phosphatase 1B | Inhibition | nan | % | 10.1016/j.bmcl.2015.08.065 |
| Homo sapiens | RPMI-8226 | GI50 | 456.04 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 1618.08 | nM | None |
| Homo sapiens | SF-268 | GI50 | 3349.65 | nM | None |
| Homo sapiens | SF-295 | GI50 | 4819.48 | nM | None |
| Homo sapiens | SF-539 | GI50 | 1819.7 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 6353.31 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 3083.19 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 2805.43 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 11015.39 | nM | None |
| Homo sapiens | SN12C | GI50 | 3698.28 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 4709.77 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 4265.8 | nM | None |
| Homo sapiens | Solute carrier organic anion transporter family member 1B1 | Inhibition | 170.67 | % | 10.1124/mol.112.084152 |
| Homo sapiens | Solute carrier organic anion transporter family member 1B3 | Inhibition | 101.94 | % | 10.1124/mol.112.084152 |
| Homo sapiens | SR | GI50 | 794.33 | nM | None |
| Homo sapiens | SW-620 | GI50 | 2349.63 | nM | None |
| Homo sapiens | T47D | GI50 | 10375.28 | nM | None |
| Homo sapiens | T47D | IC50 | 7400.0 | nM | 10.1016/j.bmcl.2011.05.113 |
| Homo sapiens | T98G | IC50 | 100000.0 | nM | 10.1021/jm800993r |
| Homo sapiens | TK-10 | GI50 | 4365.16 | nM | None |
| Homo sapiens | Transient receptor potential cation channel subfamily A member 1 | Activity | nan | None | 10.1021/acs.jnatprod.5b00272 |
| Homo sapiens | Transient receptor potential cation channel subfamily A member 1 | EC50 | 250.0 | nM | 10.1021/acs.jnatprod.5b00272 |
| Homo sapiens | Transient receptor potential cation channel subfamily A member 1 | EC50 | 319.0 | nM | 10.1021/jm100062h |
| Homo sapiens | Transient receptor potential cation channel subfamily A member 1 | EC50 | 10964.78 | nM | 10.1021/jm100477n |
| Homo sapiens | Transient receptor potential cation channel subfamily A member 1 | EC50 | 15488.17 | nM | 10.1021/jm100477n |
| Homo sapiens | Transient receptor potential cation channel subfamily A member 1 | EC50 | 23988.33 | nM | 10.1021/jm100477n |
| Homo sapiens | Transient receptor potential cation channel subfamily A member 1 | EC50 | 27542.29 | nM | 10.1021/jm100477n |
| Homo sapiens | Transient receptor potential cation channel subfamily A member 1 | max activation | 95.0 | % | 10.1021/acs.jnatprod.5b00272 |
| Homo sapiens | U-251 | GI50 | 3069.02 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 3147.75 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 3318.94 | nM | None |
| Homo sapiens | UACC-903 | Activity | 40.0 | % | 10.1021/jm800993r |
| Homo sapiens | UACC-903 | Activity | nan | None | 10.1021/jm800993r |
| Homo sapiens | UACC-903 | IC50 | 15000.0 | nM | 10.1021/jm800993r |
| Homo sapiens | Ubiquitin carboxyl-terminal hydrolase 1 | Potency | 44668.4 | nM | None |
| Homo sapiens | Ubiquitin carboxyl-terminal hydrolase 7 | K | nan | None | 10.1016/j.bmcl.2018.11.055 |
| Homo sapiens | UO-31 | GI50 | 2716.44 | nM | None |
| Homo sapiens | Vanilloid receptor | Activity | nan | None | 10.1021/acs.jnatprod.5b00272 |
| Homo sapiens | Vanilloid receptor | EC50 | 223000.0 | nM | 10.1021/acs.jnatprod.5b00272 |
| Homo sapiens | Vanilloid receptor | max activation | 49.0 | % | 10.1021/acs.jnatprod.5b00272 |
| Homo sapiens | Vitamin D receptor | Potency | 39810.7 | nM | None |
| Leishmania donovani | Leishmania donovani | Inhibition | nan | % | 10.1016/j.bmc.2019.115185 |
| Meloidogyne javanica | Meloidogyne javanica | LC50 | 4.48 | ug.mL-1 | 10.1016/j.cropro.2010.09.004 |
| Meloidogyne javanica | Meloidogyne javanica | LC90 | 8.55 | ug ml-1 | 10.1016/j.cropro.2010.09.004 |
| Meloidogyne javanica | Meloidogyne javanica | mortality | 32.25 | % | 10.1016/j.cropro.2010.09.004 |
| Meloidogyne javanica | Meloidogyne javanica | mortality | 70.25 | % | 10.1016/j.cropro.2010.09.004 |
| Mus musculus | 4T1 | Activity | 36.0 | None | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | 4T1 | TGI | 18.1 | % | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | 4T1 | TGI | 26.8 | % | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Glutathione S-transferase Mu 1 | Ratio | 0.89 | None | 10.1021/jm00079a025 |
| Mus musculus | Glutathione S-transferase Mu 1 | Ratio | 1.0 | None | 10.1021/jm00079a025 |
| Mus musculus | Glutathione S-transferase Mu 1 | Ratio | 1.04 | None | 10.1021/jm00079a025 |
| Mus musculus | Glutathione S-transferase Mu 1 | Ratio | 1.64 | None | 10.1021/jm00079a025 |
| Mus musculus | Glutathione S-transferase Mu 1 | Ratio | 1.71 | None | 10.1021/jm00079a025 |
| Mus musculus | Glutathione S-transferase Mu 1 | Ratio | 2.35 | None | 10.1021/jm00079a025 |
| Mus musculus | Mus musculus | Activity | 0.13 | g | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | 0.245 | g | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | 0.428 | g | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | 1.21 | g | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | 5.6 | mmol/L | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | 8.8 | 10'6 /uL | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | 9.7 | umol/L | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | 16.0 | g/dl | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | 21.5 | U/L | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | 45.1 | % | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | 158.6 | U/L | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | 300.8 | 10'3 /uL | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | 871.0 | 10'3 /uL | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | nan | None | 10.1016/j.ejmech.2017.03.028 |
| Mus musculus | Mus musculus | Activity | nan | None | 10.1021/jm800993r |
| Mus musculus | Nuclear receptor ROR-gamma | Potency | 5623.4 | nM | None |
| Mus musculus | Nuclear receptor ROR-gamma | Potency | 22387.2 | nM | None |
| Mus musculus | Transient receptor potential cation channel subfamily M member 8 | Activity | nan | None | 10.1021/acs.jnatprod.5b00272 |
| Rattus norvegicus | Cytochrome P450 2B1 | Ki | 5800.0 | nM | 10.2174/138920005774330639 |
| Rattus norvegicus | Cytochrome P450 2B1 | kinact | 0.66 | min-1 | 10.2174/138920005774330639 |
| Rattus norvegicus | Cytochrome P450 2B1 | partition_ratio | 9.0 | None | 10.2174/138920005774330639 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | EC50 | 60100.0 | nM | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | EC50 | 75100.0 | nM | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | EC50 | 676000.0 | nM | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | GI | 5.0 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | GI | 35.0 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | GI | 37.0 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | GI | 71.2 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | GI | 78.2 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | GI | 100.0 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | Inhibition | 6.7 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | Inhibition | 36.7 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | Inhibition | 53.3 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | Inhibition | 55.0 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | Inhibition | 62.5 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | Inhibition | 63.3 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | Inhibition | 72.5 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | Inhibition | 92.5 | % | 10.1002/ps.2126 |
| Sclerotinia sclerotiorum | Sclerotinia sclerotiorum | Inhibition | 100.0 | % | 10.1002/ps.2126 |
| Severe acute respiratory syndrome coronavirus 2 | Replicase polyprotein 1ab | IC50 relative | 20.0 | uM | 10.6019/EOS300041 |
| Severe acute respiratory syndrome coronavirus 2 | Replicase polyprotein 1ab | IC50 relative | 20.0 | uM | 10.6019/EOS300044 |
| Severe acute respiratory syndrome coronavirus 2 | Replicase polyprotein 1ab | Inhibition | 4.86 | % | 10.6019/CHEMBL4495564 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | Inhibition | 0.03 | % | 10.6019/CHEMBL4495565 |
| Trypanosoma brucei rhodesiense | Trypanosoma brucei rhodesiense | Inhibition | 50.0 | % | 10.1016/j.bmc.2019.115185 |
| Trypanosoma cruzi | Trypanosoma cruzi | Inhibition | nan | % | 10.1016/j.bmc.2019.115185 |
| None | ADMET | Activity | nan | None | 10.1021/acs.jnatprod.5b00272 |
| None | NON-PROTEIN TARGET | IC50 | 19800.0 | nM | 10.1016/j.bmcl.2015.11.045 |
| None | Unchecked | Activity | 3.0 | % | 10.1016/j.ejmech.2018.10.010 |
| None | Unchecked | Activity | 22.0 | % | 10.1016/j.ejmech.2018.10.010 |
| None | Unchecked | Activity | 41.0 | % | 10.1016/j.ejmech.2018.10.010 |
| None | Unchecked | Activity | 64.6 | % | 10.1016/j.ejmech.2017.03.028 |
| None | Unchecked | Activity | 100.0 | % | 10.1016/j.ejmech.2018.10.010 |
| None | Unchecked | Activity | nan | None | 10.1016/j.ejmech.2017.03.028 |
| None | Unchecked | FC | 9.4 | None | 10.1016/j.ejmech.2017.03.028 |
| None | Unchecked | IC50 | 3700.0 | nM | 10.1016/j.ejmech.2018.10.010 |
| None | Unchecked | IC50 | 19800.0 | nM | 10.1016/j.bmcl.2018.06.042 |
| None | Unchecked | IC50 | 19800.0 | nM | 10.1016/j.ejmech.2017.03.028 |
| None | Unchecked | Potency | 891.3 | nM | None |
| None | Unchecked | Potency | 11220.2 | nM | None |