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Iboxygaine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Iboga Alkaloid
| Canonical Smiles | COc1ccc2c(c1)c1CCN3[C@@H]4[C@H](c1[nH]2)C[C@H](C3)C[C@H]4[C@@H](O)C |
|---|---|
| InChI | InChI=1S/C20H26N2O2/c1-11(23)15-7-12-8-17-19-14(5-6-22(10-12)20(15)17)16-9-13(24-2)3-4-18(16)21-19/h3-4,9,11-12,15,17,20-21,23H,5-8,10H2,1-2H3/t11-,12+,15-,17-,20-/m0/s1 |
| InChIKey | QLSITYRYHBQHBY-BFRPBLBHSA-N |
| Formula | C20H26N2O2 |
| HBA | 3 |
| HBD | 2 |
| MW | 326.44 |
| Rotatable Bonds | 2 |
| TPSA | 48.49 |
| LogP | 2.91 |
| Number Rings | 6 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 326.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Voacanga africana | Apocynaceae | Plantae | 141630 |
Showing of synonyms
Iboxygaine
(-)-Iboxygaine
82-55-3
(4alpha)-12-Methoxyibogamin-20S-ol
Ibogamin-20-ol, 12-methoxy-, (4alpha,20S)-
DTXSID90231508
(1S)-1-[(1R,15S,17R,18R)-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraen-17-yl]ethanol
(1S)-1-((1R,15S,17R,18R)-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraen-17-yl)ethanol
DTXCID50153999
Kimvuline
- Babiaka SB, Simoben CV, et al. (2020). Alkaloids with anti-onchocercal activity from Voacanga africana Stapf (Apocynaceae): identification and molecular modeling. Molecules, 2020, 26(1), 70. [View]
No compound-protein relationship available.
SMILES: c1cccc2[nH]c(c3c12)C4C5N(CC3)CC(C4)CC5
Level: 0
Mol. Weight: 326.44 g/mol
Anti-onchocercal
Absorption
- Caco-2 (logPapp)
- -5.08
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.270
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.15
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.420
- Plasma Protein Binding
- 62.25
- 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
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.030
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.590
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.880
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.550
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- -5.060
- Rat (Acute)
- 2.960
- Rat (Chronic Oral)
- 1.860
- Fathead Minnow
- 4.060
- 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
- 427.660
- Hydration Free Energy
- -5.700
- Log(D) at pH=7.4
- 2.100
- Log(P)
- 2.2
- Log S
- -2.87
- Log(Vapor Pressure)
- -8.77
- Melting Point
- 225.17
- pKa Acid
- 12.4
- pKa Basic
- 8.44
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.9685 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.9591 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.9521 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9370 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.8824 |
| clade A/E 93TH057 HIV-1 gp120 core | A0A0M3KKW9 | A0A0M3KKW9_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.8729 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8639 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8461 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8406 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8368 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8122 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8106 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7821 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7799 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7756 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7734 |
| Nucleoside diphosphate kinase | P15266 | NDK_MYXXA | Myxococcus xanthus | 3 | 0.7649 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7585 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7562 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7551 |
| (R)-S-adenosyl-L-methionine hydrolase | O58212 | O58212_PYRHO | Pyrococcus horikoshii OT3 | 3 | 0.7546 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7528 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7519 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7505 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7494 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7474 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7466 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7411 |
| 16S rRNA (guanine(1405)-N(7))-methyltransferase | Q763K9 | Q763K9_ECOLX | Escherichia coli | 3 | 0.7381 |
| Scytalone dehydratase | P56221 | SCYD_MAGO7 | Pyricularia oryzae | 3 | 0.7373 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7369 |
| Proto-oncogene tyrosine-protein kinase receptor Ret | P07949 | RET_HUMAN | Homo sapiens | 3 | 0.7352 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7352 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7339 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7325 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7323 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 2 | 0.7310 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7305 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7302 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7292 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 2 | 0.7272 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7267 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7257 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7221 |
| GTP 3',8-cyclase | P69848 | MOAA_STAA8 | Staphylococcus aureus | 3 | 0.7205 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 2 | 0.7205 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7199 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 2 | 0.7197 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 2 | 0.7195 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7194 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7177 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 2 | 0.7166 |
| Mitogen-activated protein kinase kinase kinase 7 | O43318 | M3K7_HUMAN | Homo sapiens | 3 | 0.7154 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7146 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7135 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.7134 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 2 | 0.7121 |
| Acidic mammalian chitinase | Q9BZP6 | CHIA_HUMAN | Homo sapiens | 2 | 0.7118 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7105 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 2 | 0.7104 |
| Pantothenate synthetase | P9WIL4 | PANC_MYCTO | Mycobacterium tuberculosis | 2 | 0.7102 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 2 | 0.7101 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7094 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7093 |
| Biotin carboxylase | P43873 | ACCC_HAEIN | Haemophilus influenzae | 2 | 0.7093 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 2 | 0.7056 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 2 | 0.7033 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7031 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 2 | 0.7023 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 2 | 0.7011 |