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Voacangarine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | COc1ccc2c(c1)c1CCN3C4[C@@](c1[nH]2)(CC(C3)C[C@@]4(C)[C@@H](O)C)OC(=O)C |
|---|---|
| InChI | InChI=1S/C23H30N2O4/c1-13(26)22(3)10-15-11-23(29-14(2)27)20-17(7-8-25(12-15)21(22)23)18-9-16(28-4)5-6-19(18)24-20/h5-6,9,13,15,21,24,26H,7-8,10-12H2,1-4H3/t13-,15?,21?,22-,23-/m0/s1 |
| InChIKey | SAJQWZOEYYGJEX-DNVZXSEGSA-N |
| Formula | C23H30N2O4 |
| HBA | 5 |
| HBD | 2 |
| MW | 398.5 |
| Rotatable Bonds | 3 |
| TPSA | 74.79 |
| LogP | 2.97 |
| Number Rings | 6 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.61 |
| Exact Mass | 398.22 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tabernaemontana brachyantha | Apocynaceae | Plantae | 761053 |
Showing of synonyms
Voacangarine
Voacristine
545-84-6
(?)-Voacangarine
Methyl (1S,15R,17S,18S)-17-[(1S)-1-hydroxyethyl]-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
NSC 306219
Ibogamine-18-carboxylic acid, 20-hydroxy-12-methoxy-, methyl ester, (20S)-
CS-0129934
- Patel Mb, Thompson LS, et al. (1973). Alcaldoïes de Tabernaemontana brachyantha. Phytochemistry, 1973, 12, 451-456. [View]
No compound-protein relationship available.
SMILES: c1cccc2[nH]c(c3c12)C4C5N(CC3)CC(C4)CC5
Level: 0
Mol. Weight: 398.5 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.94
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.120
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.1
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.800
- Plasma Protein Binding
- 47.78
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-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
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.870
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.150
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.920
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.670
- 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
- -26.480
- Rat (Acute)
- 3.160
- Rat (Chronic Oral)
- 1.850
- Fathead Minnow
- 4.080
- 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
- 459.120
- Hydration Free Energy
- -5.690
- Log(D) at pH=7.4
- 2.130
- Log(P)
- 2.46
- Log S
- -3.17
- Log(Vapor Pressure)
- -9.1
- Melting Point
- 212.12
- pKa Acid
- 9.39
- pKa Basic
- 7.17
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member B10 | O60218 | AK1BA_HUMAN | Homo sapiens | 3 | 0.7200 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7160 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7015 |