Select a section from the left sidebar
14-hydroxy-N-methyl canadine
- Family: Plantae - Papaveraceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid
| Canonical Smiles | COc1c(OC)ccc2c1C[N+]1(C)CCc3c(C1(C2)O)cc1c(c3)OCO1 |
|---|---|
| InChI | InChI=1S/C21H24NO5/c1-22-7-6-13-8-18-19(27-12-26-18)9-16(13)21(22,23)10-14-4-5-17(24-2)20(25-3)15(14)11-22/h4-5,8-9,23H,6-7,10-12H2,1-3H3/q+1 |
| InChIKey | OYYYRRRQDQTELE-UHFFFAOYSA-N |
| Formula | C21H24NO5+ |
| HBA | 5 |
| HBD | 1 |
| MW | 370.43 |
| Rotatable Bonds | 2 |
| TPSA | 57.15 |
| LogP | 2.34 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 27 |
| Formal Charge | 1 |
| Fraction CSP3 | 0.43 |
| Exact Mass | 370.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Glaucium arabicum | Papaveraceae | Plantae | 2072396 |
Showing of synonyms
14-hydroxy-N-methyl canadine
- Elbermawi A, Sallam A, et al. (2018). Bioactive isoquinoline alkaloids from Glaucium arabicum. Phytochemistry Letters, 2018, 28, 139-144. [View]
Pubchem:
131676006
No compound-protein relationship available.
SMILES: O1COc(c12)cc3c(c2)C4[NH+](CC3)Cc5c(C4)cccc5
Level: 0
Mol. Weight: 370.43 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.12
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.530
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.72
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.780
- Plasma Protein Binding
- 40.14
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.820
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.540
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.930
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 8.300
- 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
- -9.730
- Rat (Acute)
- 2.690
- Rat (Chronic Oral)
- 1.030
- Fathead Minnow
- 4.700
- 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
- 421.950
- Hydration Free Energy
- -7.430
- Log(D) at pH=7.4
- 1.350
- Log(P)
- -1.14
- Log S
- -0.82
- Log(Vapor Pressure)
- -9.21
- Melting Point
- 226.28
- pKa Acid
- 9.0
- pKa Basic
- 3.33
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9399 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.9226 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.9113 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8996 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.8871 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.8715 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 4 | 0.8693 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8636 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8594 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8476 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.8453 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.8306 |
| Nodulin-13 | P93330 | NOD13_MEDTR | Medicago truncatula | 3 | 0.8181 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.8163 |
| FMN-dependent NAD(P)H:quinone oxidoreductase 1 | Q9I5F3 | AZOR1_PSEAE | Pseudomonas aeruginosa | 4 | 0.8108 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8073 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.7845 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.7834 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7816 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7811 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7773 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 3 | 0.7760 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7671 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7640 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7632 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7600 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7596 |
| Aldehyde dehydrogenase, mitochondrial | P05091 | ALDH2_HUMAN | Homo sapiens | 3 | 0.7494 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7489 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7471 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7459 |
| Aldehyde dehydrogenase, mitochondrial | P05091 | ALDH2_HUMAN | Homo sapiens | 3 | 0.7393 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7301 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7299 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7286 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7258 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7219 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 3 | 0.7217 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7215 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7160 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7141 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7080 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7073 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 2 | 0.7070 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7026 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.7017 |