Voaphylline hydroxyindolenine






Names

    • Voaphylline indolenine, hydroxy-
    • Voaphylline hydroxyindolenine
    • 15-ethyl-17-oxa-1,11-diazapentacyclo(13.4.1.04,12.05,10.016,18)icosa-5,7,9,11-tetraen-4-ol
    • 2H-3,13-Methanooxireno(9,10)azacycloundecino(5,4-b)indol-5a(1aH)-ol, 13-ethyl-4,5,11,12,13,13a-hexahydro-, (1ar-(1ar*,5ar*,13S*,13as*))-
    • DTXSID70939611
    • (1aR,5aR,13S,13aS)-13-Ethyl-4,5,11,12,13,13a-hexahydro-2H-3,13-methanooxireno[9,10]azacycloundecino[
    • 13-Ethyl-1a,2,4,5,11,12,13,13a-octahydro-5aH-3,13-methanooxireno[9,10]azacycloundecino[5,4-b]indol-5a-ol
    • 15-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-5,7,9,11-tetraen-4-ol
    • 2H-3,13-Methanooxireno[9,10]azacycloundecino[5,4-b]indol-5a(1aH)-ol, 13-ethyl-4,5,11,12,13,13a-hexahydro-, [1ar-(1ar*,5ar*,13S*,13as*)]-
    • 2H-3,13-Methanooxireno[9,10]azacycloundecino[5,4-b]indol-5a(1aH)-ol, 13-ethyl-4,5,11,12,13,13a-hexahydro-, [1aR-(1a.alpha.,5a.beta.,13.beta.,13a.alpha.)]-
    • 2H-3,13-Methanooxireno(9,10)azacycloundecino(5,4-b)indol-5a(1aH)-ol, 13-ethyl-4,5,11,12,13,13a-hexahydro-, (1aR-(1aalpha,5abeta,13beta,13aalpha))-
    • Voaphylline hydroxyindolenine (neutral)
    • 18269-16-4
    • Voaphylline indolenine

Attributes

  • Canonical SMILES

    CCC1CC2CC3(C1N(C2)CCC4(C3=NC5=C4C=C(C=C5)OC)O)C(=O)OC

  • InChI

    InChI=1S/C22H28N2O4/c1-4-14-9-13-11-21(20(25)28-3)18(14)24(12-13)8-7-22(26)16-10-15(27-2)5-6-17(16)23-19(21)22/h5-6,10,13-14,18,26H,4,7-9,11-12H2,1-3H3

  • Molecule Class: Alkaloids
  • TPSA: 71.36
  • #RotBonds: 3
  • MW: 384.4760000000001
  • HBD: 1
  • HBA: 6
  • logP: 2.652400000000001
  • Chemical Formula: C22H28N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. officinalis China - Cai20120227

External Databases


References

  • Accumulation of indole alkaloids in a suspension culture of Tabernaemontana divaricata. Planta Med, 1988 (PMID 17265301).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.

Predicted ADMET Properties

    Property Model Name Predicted Value
    Absorption Caco-2 (logPaap) -5.07
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.9
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.98
    Distribution Blood-Brain Barrier (Central Nervous System) -2.29
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.75
    Plasma Protein Binding 33.61
    Steady State Volume of Distribution 2.54
    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 Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 5.3
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.17
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.08
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.12
    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 -14.88
    Rat (Acute) 3.28
    Rat (Chronic Oral) 1.85
    Fathead Minnow 4.49
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 434.0
    Hydration Free Energy -6.04
    Log(D) at pH=7.4 2.58
    Log(P) 2.24
    Log S -3.29
    Log(Vapor Pressure) -7.81
    Melting Point 163.98
    pKa Acid 7.39
    pKa Basic 6.44