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N-methyl-sec-isopseudostrychnine
- Family: Plantae - Loganiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Monoindole Alkaloid
| Canonical Smiles | OC/C=C\1/CN(C)CC[C@@]23C(=O)C[C@@H]1C1=CCC(=O)N([C@H]21)c1c3cccc1 |
|---|---|
| InChI | InChI=1S/C22H24N2O3/c1-23-10-9-22-17-4-2-3-5-18(17)24-20(27)7-6-15(21(22)24)16(12-19(22)26)14(13-23)8-11-25/h2-6,8,16,21,25H,7,9-13H2,1H3/b14-8-/t16-,21-,22+/m0/s1 |
| InChIKey | QQQSTRCKRSZLNQ-KWGOCHSZSA-N |
| Formula | C22H24N2O3 |
| HBA | 4 |
| HBD | 1 |
| MW | 364.45 |
| Rotatable Bonds | 1 |
| TPSA | 60.85 |
| LogP | 1.81 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.45 |
| Exact Mass | 364.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Strychnos icaja | Loganiaceae | Plantae | 1040889 |
Showing of synonyms
N-methyl-sec-isopseudostrychnine
- Tchinda A, Tamze V, et al. (2012). Alkaloids from the stem bark of Strychnos icaja. Phytochemistry Letters, 2012, 5(1), 108-113. [View]
Pubchem:
162866297
Zinc:
ZINC000238779806
No compound-protein relationship available.
SMILES: C1CNCC(=C)C(CC2=O)C(=CCC3=O)C4N3c(c5C124)cccc5
Level: 0
Mol. Weight: 364.45 g/mol
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -4.75
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.6
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.1
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.8
- Plasma Protein Binding
- 56.79
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- 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
- 11.96
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.34
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.05
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.67
- 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
- -11.46
- Rat (Acute)
- 3.05
- Rat (Chronic Oral)
- 1.96
- Fathead Minnow
- 4.5
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 485.28
- Hydration Free Energy
- -6.37
- Log(D) at pH=7.4
- 0.69
- Log(P)
- 0.42
- Log S
- -3.19
- Log(Vapor Pressure)
- -10.9
- Melting Point
- 229.27
- pKa Acid
- 6.09
- pKa Basic
- 5.51
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.9168 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.9079 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8838 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8789 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8702 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8292 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8093 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.8082 |
| Acidic mammalian chitinase | Q9BZP6 | CHIA_HUMAN | Homo sapiens | 3 | 0.8069 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7685 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7656 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7414 |
| Nicotinamide riboside kinase 1 | Q9NWW6 | NRK1_HUMAN | Homo sapiens | 3 | 0.7283 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7282 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7267 |
| Putative FAD-dependent oxygenase EncM | Q9KHK2 | Q9KHK2_9ACTN | Streptomyces maritimus | 3 | 0.7250 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7226 |
| Ribosome-inactivating protein alpha-trichosanthin | P09989 | RIPT_TRIKI | Trichosanthes kirilowii | 3 | 0.7178 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7137 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7105 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7105 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7060 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7059 |
| Plasma membrane ATPase 3 | Q08436 | PMA3_NICPL | Nicotiana plumbaginifolia | 4 | 0.7038 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7037 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7021 |