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Voachalotine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | C/C=C\1/CN2C3CC1C(C2Cc1c3n(C)c2c1cccc2)(CO)C(=O)OC |
|---|---|
| InChI | InChI=1S/C22H26N2O3/c1-4-13-11-24-18-10-16(13)22(12-25,21(26)27-3)19(24)9-15-14-7-5-6-8-17(14)23(2)20(15)18/h4-8,16,18-19,25H,9-12H2,1-3H3/b13-4- |
| InChIKey | IWEYXWIPVZEVPT-PQMHYQBVSA-N |
| Formula | C22H26N2O3 |
| HBA | 5 |
| HBD | 1 |
| MW | 366.46 |
| Rotatable Bonds | 2 |
| TPSA | 54.7 |
| LogP | 2.58 |
| Number Rings | 6 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 366.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tabernaemontana penduliflora | Apocynaceae | Plantae | 761088 |
Showing of synonyms
Voachalotine
664-25-5
EINECS 211-556-0
NSC 180537
Methyl (16R)-17-hydroxy-1-methylsarpagan-16-carboxylate
MLS000863636
MEGxp0_001807
CHEMBL1368524
Sarpagan-16-carboxylic acid, 17-hydroxy-1-methyl-, methyl ester, (16R)-
ACon0_000899
ACon1_002344
HMS2269B11
SMR000440749
No compound-protein relationship available.
SMILES: C=C(C1)C(C2)CC(C3)N1C2c(c3c45)[nH]c4cccc5
Level: 0
Mol. Weight: 366.46 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.85
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.84
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.54
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.92
- Plasma Protein Binding
- 16.16
- 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
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.61
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- 0.1
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.01
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.96
- 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
- -10.26
- Rat (Acute)
- 3.34
- Rat (Chronic Oral)
- 1.92
- Fathead Minnow
- 5.01
- 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
- 460.16
- Hydration Free Energy
- -5.01
- Log(D) at pH=7.4
- 2.38
- Log(P)
- 2.63
- Log S
- -2.88
- Log(Vapor Pressure)
- -8.39
- Melting Point
- 172.12
- pKa Acid
- 7.94
- pKa Basic
- 7.85
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.9320 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.9216 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.9132 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.9057 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8620 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8059 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7915 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7875 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7786 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7719 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7564 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7451 |
| Genome polyprotein | Q99AU2 | Q99AU2_9HEPC | Hepatitis C virus subtype 1b | 4 | 0.7377 |
| Retinaldehyde-binding protein 1 | P12271 | RLBP1_HUMAN | Homo sapiens | 4 | 0.7327 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7149 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7141 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7140 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 4 | 0.7083 |
| Aldo-keto reductase family 1 member B1 | P80276 | ALDR_PIG | Sus scrofa | 3 | 0.7047 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7035 |