5,6-dioxo-11-hydroxy voacangine - Compound Card

5,6-dioxo-11-hydroxy voacangine

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5,6-dioxo-11-hydroxy voacangine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Iboga Alkaloid
Canonical Smiles [nH]1c2c(c3cc(c(cc13)O)OC)C(=O)C(=O)N1[C@@H]3[C@]2(C[C@H](C[C@@H]3CC)C1)C(=O)OC
InChI InChI=1S/C22H24N2O6/c1-4-11-5-10-8-22(21(28)30-3)18-16(17(26)20(27)24(9-10)19(11)22)12-6-15(29-2)14(25)7-13(12)23-18/h6-7,10-11,19,23,25H,4-5,8-9H2,1-3H3/t10-,11-,19-,22+/m0/s1
InChIKey BHEKELYIIJBVLG-PIFOQHIJSA-N
Formula C22H24N2O6
HBA 6
HBD 2
MW 412.44
Rotatable Bonds 3
TPSA 108.93
LogP 2.14
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 412.16
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: 412.44 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.23
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.920
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.840
Plasma Protein Binding
62.36
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.560
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.740
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.540
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.440
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
-48.020
Rat (Acute)
2.660
Rat (Chronic Oral)
2.550
Fathead Minnow
4.040
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
489.500
Hydration Free Energy
-3.660
Log(D) at pH=7.4
2.210
Log(P)
1.59
Log S
-4.57
Log(Vapor Pressure)
-9.18
Melting Point
321.3
pKa Acid
7.01
pKa Basic
5.65

No predicted protein targets found for this compound.

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