Ibogamine-16-carboxylic acid-17,20-didehydro-5,6-dioxo-10-methoxy-methyl ester - Compound Card

Ibogamine-16-carboxylic acid-17,20-didehydro-5,6-dioxo-10-methoxy-methyl ester

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Ibogamine-16-carboxylic acid-17,20-didehydro-5,6-dioxo-10-methoxy-methyl ester

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Iboga Alkaloid
Canonical Smiles c1(ccc2c(c1)c1c([nH]2)[C@]2([C@H]3N(C(=O)C1=O)C[C@H](C2)C[C@@H]3CC)C(=O)OC)OC
InChI InChI=1S/C22H24N2O5/c1-4-12-7-11-9-22(21(27)29-3)18-16(17(25)20(26)24(10-11)19(12)22)14-8-13(28-2)5-6-15(14)23-18/h5-6,8,11-12,19,23H,4,7,9-10H2,1-3H3/t11-,12-,19-,22+/m0/s1
InChIKey UVNSBASVOODKQP-LDBZZREISA-N
Formula C22H24N2O5
HBA 5
HBD 1
MW 396.44
Rotatable Bonds 3
TPSA 88.7
LogP 2.43
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 396.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tabernaemontana inconspicua Apocynaceae Plantae 761075

Showing of synonyms

  • Foudjo Melacheu Laura G, Mfotie Njoya E, et al. (2021). A new cytotoxic indole alkaloid from Tabernaemontana inconspicua stapf. Natural product research,2021, 35(10), 1590-1595. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc2[nH]c(c3c12)C4C5N(C(=O)C3=O)CC(C4)CC5

Level: 0

Mol. Weight: 396.44 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.94
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.8
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.83
Plasma Protein Binding
60.44
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
Substrate
CYP 2C9 Inhibitor
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
6.67
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.35
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.77
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.31
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
-32.96
Rat (Acute)
3.02
Rat (Chronic Oral)
2.44
Fathead Minnow
4.05
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
474.41
Hydration Free Energy
-4.79
Log(D) at pH=7.4
2.72
Log(P)
2.52
Log S
-4.51
Log(Vapor Pressure)
-8.73
Melting Point
288.09
pKa Acid
7.39
pKa Basic
5.5
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8740
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8384
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7760
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7666
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7624
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7273
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7242
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7169
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7080

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