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Methylscopolamine
- Family: Plantae - Solanaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | OCC(c1ccccc1)C(=O)OC1CC2C3C(C(C1)[N+]2(C)C)O3 |
|---|---|
| InChI | InChI=1S/C18H24NO4/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11/h3-7,12-17,20H,8-10H2,1-2H3/q+1 |
| InChIKey | LZCOQTDXKCNBEE-UHFFFAOYSA-N |
| Formula | C18H24NO4+ |
| HBA | 4 |
| HBD | 1 |
| MW | 318.39 |
| Rotatable Bonds | 4 |
| TPSA | 59.06 |
| LogP | 1.06 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 23 |
| Formal Charge | 1 |
| Fraction CSP3 | 0.61 |
| Exact Mass | 318.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Datura stramonium | Solanaceae | Plantae | 4076 |
Showing of synonyms
Methylscopolamine
Pamine Bromide
NSC61809
NSC-61809
(-)-Tropate(ester)
Scopolammonium, bromide
Scopolamin methylbromide
Methscopolamine methylbromide
CHEMBL293927
WLN: T C356 A AK DOTJ A1 A1 HOVYR & 1Q & Q & E
1.alpha.-H, 6.beta.,7.beta.-epoxy-3.alpha.-hydroxy-8-methyl-, bromide, (-)-tropate
1.alpha.H, 6.beta.,7.beta.-epoxy-3.alpha.-hydroxy-8-methyl-, bromide, (-)-tropate
3-Oxa-9-azoniatricyclo[3.3.1.02, 7-(3-hydroxy-1-oxo-2-phenylpropoxy)-9,9-dimethyl-, bromide, [7(S)-(1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)]-
SCHEMBL158622
CHEMBL107979
DTXSID90859307
BCP34407
NMS
BDBM50015727
NSC120606
N-Methylscopolamine
N-methyl scopolamine
NCGC00162342-01
NCGC00162342-02
NS00096432
L001039
9,9-dimethyl-3-oxa-95-azatricyclo[3.3.1.0~2,4~]non-7-yl tropate
7-(3-Hydroxy-2-phenyl-propionyloxy)-9,9-dimethyl-3-oxa-9-azonia-tricyclo[3.3.1.0*2,4*]nonane
Bromide(scopolamine methyl bromide)
7-[(3-Hydroxy-2-phenylpropanoyl)oxy]-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]nonan-9-ium
CPRiL:
5973
SMILES: C12C(O2)C3CC(CC1[NH2+]3)OC(=O)Cc4ccccc4
Level: 1
Mol. Weight: 318.39 g/mol
SMILES: C12C(O2)C3CCCC1[NH2+]3
Level: 0
Mol. Weight: 318.39 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 318.39 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.03
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -4.51
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.93
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.24
- Plasma Protein Binding
- -4.5
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 15.91
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.78
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.12
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.99
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 2.6
- Rat (Acute)
- 3.24
- Rat (Chronic Oral)
- 1.1
- Fathead Minnow
- 4.28
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 389.68
- Hydration Free Energy
- -8.59
- Log(D) at pH=7.4
- -0.85
- Log(P)
- -2.01
- Log S
- -0.88
- Log(Vapor Pressure)
- -7.88
- Melting Point
- 159.23
- pKa Acid
- 5.18
- pKa Basic
- 4.31
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.9282 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.9282 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.8961 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.8961 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8676 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8676 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8637 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8637 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8530 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8530 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8269 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8269 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8248 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8248 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8183 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8183 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8168 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8168 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.8158 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.8158 |
| Chloramphenicol 3-O phosphotransferase | Q56148 | CPT_STRVP | Streptomyces venezuelae | 3 | 0.8151 |
| Chloramphenicol 3-O phosphotransferase | Q56148 | CPT_STRVP | Streptomyces venezuelae | 3 | 0.8151 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8012 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8012 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7966 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7966 |
| Lethal factor | P15917 | LEF_BACAN | Bacillus anthracis | 3 | 0.7840 |
| Lethal factor | P15917 | LEF_BACAN | Bacillus anthracis | 3 | 0.7840 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7828 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7828 |
| Gag-Pol polyprotein | P03369 | POL_HV1A2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7814 |
| Gag-Pol polyprotein | P03369 | POL_HV1A2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7814 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7781 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7781 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7776 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7776 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7747 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7747 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7718 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7718 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7604 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7604 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7601 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7601 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 2 | 0.7548 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 2 | 0.7548 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7523 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7523 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7514 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7514 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7497 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7497 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7457 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7457 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7452 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7452 |
| AcsD | Q93AT8 | Q93AT8_DICCH | Dickeya chrysanthemi | 3 | 0.7414 |
| AcsD | Q93AT8 | Q93AT8_DICCH | Dickeya chrysanthemi | 3 | 0.7414 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7393 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7393 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7370 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7370 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7354 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7354 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7346 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7346 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7338 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7338 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 2 | 0.7305 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 2 | 0.7305 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7302 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7302 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7288 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7288 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7239 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7239 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7238 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.7238 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7187 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7187 |
| Glucanase | Q7LHI2 | Q7LHI2_PHACH | Phanerodontia chrysosporium | 2 | 0.7172 |
| Glucanase | Q7LHI2 | Q7LHI2_PHACH | Phanerodontia chrysosporium | 2 | 0.7172 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7162 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7162 |
| 4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic | P49235 | HGGL1_MAIZE | Zea mays | 2 | 0.7156 |
| 4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic | P49235 | HGGL1_MAIZE | Zea mays | 2 | 0.7156 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7135 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7135 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7132 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7132 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7124 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7124 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7122 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7122 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.7116 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.7116 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7095 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7095 |
| Agglutinin alpha chain | P18674 | LECA_MACPO | Maclura pomifera | 3 | 0.7094 |
| Agglutinin alpha chain | P18674 | LECA_MACPO | Maclura pomifera | 3 | 0.7094 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7071 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7071 |
| Cystathionine gamma-synthase | P56069 | METB_HELPY | Helicobacter pylori | 3 | 0.7064 |
| Cystathionine gamma-synthase | P56069 | METB_HELPY | Helicobacter pylori | 3 | 0.7064 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7056 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7056 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7050 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7050 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 3 | 0.7018 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 3 | 0.7018 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7016 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7016 |