Tabernanthine - Compound Card

Tabernanthine

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Tabernanthine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Iboga Alkaloid
Canonical Smiles CC[C@H]1C[C@H]2CN3[C@@H]1[C@@H](C2)c1[nH]c2c(c1CC3)ccc(c2)OC
InChI InChI=1S/C20H26N2O/c1-3-13-8-12-9-17-19-16(6-7-22(11-12)20(13)17)15-5-4-14(23-2)10-18(15)21-19/h4-5,10,12-13,17,20-21H,3,6-9,11H2,1-2H3/t12-,13+,17+,20+/m1/s1
InChIKey UCIDWKVIQZIKEK-CFDPKNGZSA-N
Formula C20H26N2O
HBA 2
HBD 1
MW 310.44
Rotatable Bonds 2
TPSA 28.26
LogP 3.94
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 310.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Voacanga africana Apocynaceae Plantae 141630

Showing of synonyms

  • 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]
Pubchem: 6326116
Nmrshiftdb2: 70026903
CPRiL: 29400
Structure

SMILES: c1cccc2[nH]c(c3c12)C4C5N(CC3)CC(C4)CC5

Level: 0

Mol. Weight: 310.44 g/mol

Anti-onchocercal

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.51
Plasma Protein Binding
62.53
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
9.31
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.17
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.09
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.36
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
-2.45
Rat (Acute)
2.99
Rat (Chronic Oral)
1.7
Fathead Minnow
4.07
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
411.91
Hydration Free Energy
-4.55
Log(D) at pH=7.4
3.17
Log(P)
3.73
Log S
-3.18
Log(Vapor Pressure)
-7.62
Melting Point
198.04
pKa Acid
12.85
pKa Basic
8.66
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9469
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9226
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9183
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9101
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.9071
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9063
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9004
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8990
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8926
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8789
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8782
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8717
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8642
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8565
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8292
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8272
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8117
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7957
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7890
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7864
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7860
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7845
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7798
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7771
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7755
clade A/E 93TH057 HIV-1 gp120 core A0A0M3KKW9 A0A0M3KKW9_9HIV1 Human immunodeficiency virus 1 3 0.7712
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7683
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7663
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7580
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7518
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7514
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7431
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7417
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7411
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7378
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7378
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7359
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7348
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7339
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7333
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7332
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7292
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7279
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7277
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7259
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7255
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7242
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7238
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7237
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7229
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7155
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7117
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7106
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7087
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7067
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7055
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7020
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7019
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7016
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7005

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