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Irniine
- Family: Plantae - Araceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolidine Alkaloid
| Canonical Smiles | CN1CCC[C@H]1CCCCCCCCCc1ccccc1 |
|---|---|
| InChI | InChI=1S/C20H33N/c1-21-18-12-17-20(21)16-11-6-4-2-3-5-8-13-19-14-9-7-10-15-19/h7,9-10,14-15,20H,2-6,8,11-13,16-18H2,1H3/t20-/m1/s1 |
| InChIKey | MNVHQKNDNJJRIX-HXUWFJFHSA-N |
| Formula | C20H33N |
| HBA | 1 |
| HBD | 0 |
| MW | 287.49 |
| Rotatable Bonds | 10 |
| TPSA | 3.24 |
| LogP | 5.44 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.7 |
| Exact Mass | 287.26 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Arisarum vulgare | Araceae | Plantae | 267624 |
Showing of synonyms
Irniine
(2R)-1-Methyl-2-(9-phenylnonyl)pyrrolidine
CHEMBL490575
- Melhaoui A, Jossang A and Bodo B (1992). Structure of irniine, a pyrrolidine alkaloid from Arisarum vulgare. Journal of Natural Products,1992,55(7),950-952. [View]
No compound-protein relationship available.
SMILES: N1CCCC1CCCCCCCCCc2ccccc2
Level: 1
Mol. Weight: 287.49 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 287.49 g/mol
SMILES: C1CCNC1
Level: 0
Mol. Weight: 287.49 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.88
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.42
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -3.52
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.84
- Plasma Protein Binding
- 58.36
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- 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
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.46
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.49
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.1
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.46
- Micronucleos
- Safe
- 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
- 3.82
- Rat (Acute)
- 2.66
- Rat (Chronic Oral)
- 2.01
- Fathead Minnow
- 3.98
- 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
- 353.25
- Hydration Free Energy
- -2.96
- Log(D) at pH=7.4
- 4.22
- Log(P)
- 6.25
- Log S
- -4.39
- Log(Vapor Pressure)
- -4.99
- Melting Point
- 25.2
- pKa Acid
- 10.04
- pKa Basic
- 9.13
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7853 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7853 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7773 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7773 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7717 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7717 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7608 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7608 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7597 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7597 |
| Mitomycin-binding protein | O05205 | O05205_STRLA | Streptomyces lavendulae | 2 | 0.7584 |
| Mitomycin-binding protein | O05205 | O05205_STRLA | Streptomyces lavendulae | 2 | 0.7584 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7579 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7579 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7575 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7575 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 2 | 0.7567 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 2 | 0.7567 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7554 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7554 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7493 |
| Bifunctional glutamate/proline--tRNA ligase | P07814 | SYEP_HUMAN | Homo sapiens | 2 | 0.7493 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7493 |
| Bifunctional glutamate/proline--tRNA ligase | P07814 | SYEP_HUMAN | Homo sapiens | 2 | 0.7493 |
| Acetyl-CoA acetyltransferase | P14611 | THIL_CUPNH | Cupriavidus necator | 2 | 0.7452 |
| Acetyl-CoA acetyltransferase | P14611 | THIL_CUPNH | Cupriavidus necator | 2 | 0.7452 |
| Proline--tRNA ligase | Q8I5R7 | SYP_PLAF7 | Plasmodium falciparum | 2 | 0.7449 |
| Proline--tRNA ligase | Q8I5R7 | SYP_PLAF7 | Plasmodium falciparum | 2 | 0.7449 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 2 | 0.7392 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 2 | 0.7392 |
| mRNA cap guanine-N7 methyltransferase | O43148 | MCES_HUMAN | Homo sapiens | 2 | 0.7387 |
| mRNA cap guanine-N7 methyltransferase | O43148 | MCES_HUMAN | Homo sapiens | 2 | 0.7387 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 2 | 0.7379 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 2 | 0.7379 |
| Polyamine oxidase FMS1 | P50264 | FMS1_YEAST | Saccharomyces cerevisiae | 2 | 0.7339 |
| Polyamine oxidase FMS1 | P50264 | FMS1_YEAST | Saccharomyces cerevisiae | 2 | 0.7339 |
| Proline--tRNA ligase | Q8I5R7 | SYP_PLAF7 | Plasmodium falciparum | 2 | 0.7329 |
| Proline--tRNA ligase | Q8I5R7 | SYP_PLAF7 | Plasmodium falciparum | 2 | 0.7329 |
| Diaminopimelate decarboxylase | A1SR00 | A1SR00_PSYIN | Psychromonas ingrahamii | 2 | 0.7320 |
| Diaminopimelate decarboxylase | A1SR00 | A1SR00_PSYIN | Psychromonas ingrahamii | 2 | 0.7320 |
| Epothilone C/D epoxidase | Q9KIZ4 | C167_SORCE | Sorangium cellulosum | 2 | 0.7310 |
| Epothilone C/D epoxidase | Q9KIZ4 | C167_SORCE | Sorangium cellulosum | 2 | 0.7310 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | A7UD81 | A7UD81_PLAFA | Plasmodium falciparum | 2 | 0.7301 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | A7UD81 | A7UD81_PLAFA | Plasmodium falciparum | 2 | 0.7301 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 2 | 0.7288 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 2 | 0.7288 |
| Proline--tRNA ligase | Q8I5R7 | SYP_PLAF7 | Plasmodium falciparum | 2 | 0.7256 |
| Proline--tRNA ligase | Q8I5R7 | SYP_PLAF7 | Plasmodium falciparum | 2 | 0.7256 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7250 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7250 |
| TamL | D3Y1I2 | D3Y1I2_9ACTN | Streptomyces sp. 307-9 | 2 | 0.7240 |
| TamL | D3Y1I2 | D3Y1I2_9ACTN | Streptomyces sp. 307-9 | 2 | 0.7240 |
| Epothilone C/D epoxidase | Q9KIZ4 | C167_SORCE | Sorangium cellulosum | 2 | 0.7194 |
| Epothilone C/D epoxidase | Q9KIZ4 | C167_SORCE | Sorangium cellulosum | 2 | 0.7194 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 2 | 0.7166 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 2 | 0.7166 |
| BMP-2-inducible protein kinase | Q9NSY1 | BMP2K_HUMAN | Homo sapiens | 2 | 0.7123 |
| BMP-2-inducible protein kinase | Q9NSY1 | BMP2K_HUMAN | Homo sapiens | 2 | 0.7123 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 2 | 0.7122 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 2 | 0.7122 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 2 | 0.7116 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 2 | 0.7116 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7107 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7107 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7092 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7092 |
| Protein arginine N-methyltransferase 1 | Q63009 | ANM1_RAT | Rattus norvegicus | 2 | 0.7083 |
| Protein arginine N-methyltransferase 1 | Q63009 | ANM1_RAT | Rattus norvegicus | 2 | 0.7083 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7073 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 2 | 0.7073 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 2 | 0.7060 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 2 | 0.7060 |
| Cytokinin dehydrogenase 1 | Q9T0N8 | CKX1_MAIZE | Zea mays | 2 | 0.7044 |
| Cytokinin dehydrogenase 1 | Q9T0N8 | CKX1_MAIZE | Zea mays | 2 | 0.7044 |
| Non-receptor tyrosine-protein kinase TYK2 | P29597 | TYK2_HUMAN | Homo sapiens | 2 | 0.7017 |
| Non-receptor tyrosine-protein kinase TYK2 | P29597 | TYK2_HUMAN | Homo sapiens | 2 | 0.7017 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7014 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7014 |