Select a section from the left sidebar
Vomicine
- Family: Plantae - Loganiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Carbazolic Alkaloid
| Canonical Smiles | CN1CC[C@@]23C(=O)C[C@H]4C(=CCO[C@@H]5[C@H]4[C@@H]2N(c2c3cccc2O)C(=O)C5)C1 |
|---|---|
| InChI | InChI=1S/C22H24N2O4/c1-23-7-6-22-14-3-2-4-15(25)20(14)24-18(27)10-16-19(21(22)24)13(9-17(22)26)12(11-23)5-8-28-16/h2-5,13,16,19,21,25H,6-11H2,1H3/t13-,16-,19-,21-,22+/m0/s1 |
| InChIKey | ZMTYENXGROJCEA-LNKPQSDASA-N |
| Formula | C22H24N2O4 |
| HBA | 5 |
| HBD | 1 |
| MW | 380.44 |
| Rotatable Bonds | 0 |
| TPSA | 70.08 |
| LogP | 1.61 |
| 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 |
| 2 | Strychnos icaja | Loganiaceae | Plantae | 1040889 |
Showing of synonyms
Vomicine
125-15-5
Strychnicine
Vomicin
UNII-4R9445MB8M
4R9445MB8M
VOMICINE [MI]
(1S,10S,22R,23R,24S)-15-hydroxy-4-methyl-9-oxa-4,13-diazahexacyclo[11.6.5.01,24.06,22.010,23.014,19]tetracosa-6,14(19),15,17-tetraene-12,20-dione
12-Hydroxy-N-methylpseudostrychnine
DTXSID30154540
4-Hydroxy-19-methyl-16,19-secostrychnidine-10,16-dione
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-hydroxy-16-methyl-, (4aR,6aS,13aS,13bR,13cS)-
16,19-Secostrychnidine-10,16-dione, 4-hydroxy-19-methyl-
(4AR,6AS,13AS,13BR,13CS)-4A,5,13,13A,13B,13C-HEXAHYDRO-10-HYDROXY-16-METHYL-12H-6A,4-(ETHANIMINOMETHANO)INDOLO(3,2,1-IJ)OXEPINO(2,3,4-DE)QUINOLINE-6,12(2H)-DIONE
12H-6a,4-(Ethaniminomethano)indolo(3,2,1-i)oxepino(2,3,4-de)quinoline-6,12(2H)-dione, 4a,5,13,13a,13b,13c-hedahydro-10-hydroxy-16-methyl-, (4aR,6aS,13aS,13bR,13cS)-
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-HYDROXY-16-METHYL-, (4AR,6AS,13AS,13BR,13CS)-
2H-6a,4-(Ethaniminomethano)indolo(3,2,1-i)oxepino(2,3,4-de)quinoline-6,12(2H)-dione, 4a,5,13,13a,13b,13c-hedahydro-10-hydroxy-16-methyl-, (4aR-(4aR*,6aS*,13aS*,13bR*,13cS*))-
1,2,3,4-tetramethoxy-10-methyl-acridin-9-one
(1S,10S,22R,23R,24S)-15-hydroxy-4-methyl-9-oxa-4,13-diazahexacyclo(11.6.5.01,24.06,22.010,23.014,19)tetracosa-6,14(19),15,17-tetraene-12,20-dione
19764-19-3
4,16-Dihydroxy-19-methyl-10-oxostrychnidinium
Strychnidinium, 4,16-dihydroxy-19-methyl-10-oxo-
DTXCID8077031
12H-6a,4-(Ethaniminomethano)indolo(3,2,1-ij)oxepino(2,3,4-de)quinolin e, 16,19-secostrychnidine-10,16-dione deriv.
12H-6a,4-(Ethaniminomethano)indolo[3,2,1-ij]oxepino[2,3,4-de]quinolin e, 16,19-secostrychnidine-10,16-dione deriv.
Strychnidinium, 4,16-dihydroxy-19-methyl-10-oxo-(9CI)
Zmtyenxgrojcea-uhfffaoysa-n
CHEBI:10019
Vomicine (Standard)
SCHEMBL3371643
CHEMBL2164625
HY-N2616R
HY-N2616
AKOS032949106
AC-34199
DA-68624
MS-26224
CS-0023019
C09255
Q27108554
(1S,10S,11R,12S,22R)-15-hydroxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2(1)?,(1)(3).0(1),(1)(2).0?,(2)(2).0(1)?,(1)?]tetracosa-6,14,16,18-tetraene-20,23-dione
- Tchinda A, Tamze V, et al. (2012). Alkaloids from the stem bark of Strychnos icaja. Phytochemistry Letters, 2012, 5(1), 108-113. [View]
- Frederich M, Hayette MP, et al. (1999). In vitro activities of Strychnos alkaloids and extracts against Plasmodium falciparum.. Antimicrobial agents and chemotherapy,1999, 43(9), 2328-31. [View] [PubMed]
Pubchem:
101595
Cas:
125-15-5
Gnps:
CCMSLIB00006493046
Zinc:
ZINC000004097975
Kegg Ligand:
C09255
Chebi:
10019
Chembl:
CHEMBL2164625
Comptox:
DTXSID30154540
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)
- -4.97
- 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
- -1.62
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.55
- Plasma Protein Binding
- 50.27
- 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
- 14.47
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.66
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.96
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.83
- 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
- -21.24
- Rat (Acute)
- 3.3
- Rat (Chronic Oral)
- 1.91
- Fathead Minnow
- 3.97
- 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
- 493.88
- Hydration Free Energy
- -5.89
- Log(D) at pH=7.4
- 0.75
- Log(P)
- 0.99
- Log S
- -3.33
- Log(Vapor Pressure)
- -10.28
- Melting Point
- 284.37
- pKa Acid
- 6.41
- pKa Basic
- 6.08
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.9286 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.9164 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.9117 |
| Adenylate cyclase 2 | A0A2U2H3Y1 | A0A384LKY8_YERPE | Yersinia pestis | 3 | 0.8016 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7921 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7679 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7603 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7549 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7420 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7280 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7260 |
| Beta-galactoside-specific lectin 1 | P81446 | ML1_VISAL | Viscum album | 3 | 0.7228 |
| Glutamate receptor 3 | P19492 | GRIA3_RAT | Rattus norvegicus | 3 | 0.7185 |
| Precorrin-3 methylase | O68097 | O68097_RHOCA | Rhodobacter capsulatus | 3 | 0.7011 |