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15-hydroxyicajine
- Family: Plantae - Loganiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Monoindole Alkaloid
| Canonical Smiles | CN1CCC23C(=O)CC4(C(=CCOC5C4C3N(c3c2cccc3)C(=O)C5)C1)O |
|---|---|
| InChI | InChI=1S/C22H24N2O4/c1-23-8-7-21-14-4-2-3-5-15(14)24-18(26)10-16-19(20(21)24)22(27,11-17(21)25)13(12-23)6-9-28-16/h2-6,16,19-20,27H,7-12H2,1H3 |
| InChIKey | AHOSVLHVFRDGQF-UHFFFAOYSA-N |
| Formula | C22H24N2O4 |
| HBA | 5 |
| HBD | 1 |
| MW | 380.44 |
| Rotatable Bonds | 0 |
| TPSA | 70.08 |
| LogP | 1.02 |
| Number Rings | 7 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.55 |
| Exact Mass | 380.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Strychnos icaja | Loganiaceae | Plantae | 1040889 |
Showing of synonyms
15-hydroxyicajine
Icajine, 14-hydroxy-
22029-96-5
16,19-Secostrychnidine-10,16-dione, 14-hydroxy-19-methyl-
14-Hydroxy-19-methyl-16,19-secostrychnidine-10,16-dione
14-Hydroxyicajine
4a-hydroxy-15-methyl-4a,5,12,12a,12b,12c-hexahydro-11h-6a,4-(ethanoiminomethano)-1-oxa-10b-azacyclohepta[1,2,3-cd]fluoranthene-6,11(2h)-dione
DTXSID20944634
AHOSVLHVFRDGQF-UHFFFAOYSA-N
- Tchinda A, Tamze V, et al. (2012). Alkaloids from the stem bark of Strychnos icaja. Phytochemistry Letters, 2012, 5(1), 108-113. [View]
Pubchem:
210990
Cas:
22029-96-5
No compound-protein relationship available.
SMILES: c1cccc(c1C234)N5C2C6C(CC3=O)C(CNCC4)=CCOC6CC5=O
Level: 0
Mol. Weight: 380.44 g/mol
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -4.92
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.63
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.68
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.52
- Plasma Protein Binding
- 27.24
- 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
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.94
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.62
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.48
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.33
- 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
- -18.5
- Rat (Acute)
- 4.2
- Rat (Chronic Oral)
- 1.85
- Fathead Minnow
- 4.35
- 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
- 470.95
- Hydration Free Energy
- -6.17
- Log(D) at pH=7.4
- 0.32
- Log(P)
- -0.14
- Log S
- -3.1
- Log(Vapor Pressure)
- -10.37
- Melting Point
- 215.1
- pKa Acid
- 5.98
- pKa Basic
- 5.8
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8128 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8062 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8042 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7829 |
| Acidic mammalian chitinase | Q9BZP6 | CHIA_HUMAN | Homo sapiens | 3 | 0.7112 |