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12-methoxyicajine
- Family: Plantae - Loganiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Monoindole Alkaloid
| Canonical Smiles | COc1cccc2c1N1C(=O)C[C@H]3[C@H]4[C@H]1[C@@]12CCN(CC(=CCO3)[C@@H]4CC1=O)C |
|---|---|
| InChI | InChI=1S/C23H26N2O4/c1-24-8-7-23-15-4-3-5-16(28-2)21(15)25-19(27)11-17-20(22(23)25)14(10-18(23)26)13(12-24)6-9-29-17/h3-6,14,17,20,22H,7-12H2,1-2H3/t14-,17-,20-,22-,23+/m0/s1 |
| InChIKey | ZKALYGURBPIPGN-PFXBBCFLSA-N |
| Formula | C23H26N2O4 |
| HBA | 5 |
| HBD | 0 |
| MW | 394.47 |
| Rotatable Bonds | 1 |
| TPSA | 59.08 |
| LogP | 1.92 |
| Number Rings | 6 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.57 |
| Exact Mass | 394.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Strychnos icaja | Loganiaceae | Plantae | 1040889 |
Showing of synonyms
12-methoxyicajine
Vomicine methyl ether
O-Methylvomicine
Vomicine methyl ether [MI]
UNII-KD5TU0Z26W
KD5TU0Z26W
12H-6a,4-(Ethaniminomethano)indolo(3,2,1-ij)oxepino(2,3,4-de)quinoline-6,12(2H)-dione, 4a,5,13,13a,13b,13c-hexahydro-10-methoxy-16-methyl-, (4ar-(4ar*,6as*,13as*,13br*,13cs*))-
5934-28-1
Q27282191
- Tchinda A, Tamze V, et al. (2012). Alkaloids from the stem bark of Strychnos icaja. Phytochemistry Letters, 2012, 5(1), 108-113. [View]
No compound-protein relationship available.
SMILES: c1cccc(c1C234)N5C2C6C(CC3=O)C(CNCC4)=CCOC6CC5=O
Level: 0
Mol. Weight: 394.47 g/mol
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -4.74
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.660
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.66
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.710
- Plasma Protein Binding
- 46.71
- 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
- 8.870
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.270
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.580
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.750
- 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
- -40.470
- Rat (Acute)
- 3.590
- Rat (Chronic Oral)
- 1.780
- Fathead Minnow
- 4.010
- 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
- 493.510
- Hydration Free Energy
- -3.830
- Log(D) at pH=7.4
- 0.990
- Log(P)
- 0.95
- Log S
- -2.54
- Log(Vapor Pressure)
- -9.87
- Melting Point
- 214.74
- pKa Acid
- 7.4
- pKa Basic
- 5.56
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Adenylate cyclase 2 | A0A2U2H3Y1 | A0A384LKY8_YERPE | Yersinia pestis | 3 | 0.8414 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7784 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7711 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7670 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7615 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7271 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7257 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7178 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7165 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7138 |