Deoxyvobtusine lactone






Names

    • Deoxyvobstusine Lactone', "methyl (1R,1'S,7'S,11'R,12R,13'R,16S,17S,22R,24'S,25'R)-19'-methoxy-9'-oxospiro(15-oxa-8,19-diazahexacyclo(10.9.1.01,9.02,7.012,16.019,22)docosa-2,4,6,9-tetraene-17,15'-8-oxa-4,17-diazaheptacyclo(11.10.1.11,4.07,11.017,24.018,23.011,25)pentacosa-18(23),19,21-triene)-10-carboxylate", "methyl (1R,1'S,7'S,11'R,12R,13'R,16S,17S,22R,24'S,25'R)-19'-methoxy-9'-oxospiro[15-oxa-8,19-diazahexacyclo[10.9.1.01,9.02,7.012,16.019,22]docosa-2,4,6,9-tetraene-17,15'-8-oxa-4,17-diazaheptacyclo[11.10.1.11,4.07,11.017,24.018,23.011,25]pentacosa-18(23),19,21-triene]-10-carboxylate"
    • Deoxyvobtusine lactone

Attributes

  • Canonical SMILES

    COC1=CC=CC2=C1N3C[C@]4(C[C@H]5[C@H]3[C@]26CCN7[C@H]6[C@@]8(C5)CC(=O)O[C@H]8CC7)CN9CC[C@@]12[C@@H]9[C@@]3([C@H]4OCC3)CC(=C1NC1=CC=CC=C21)C(=O)OC

  • InChI

    InChI=1S/C43H48N4O6/c1-50-29-9-5-7-27-32(29)47-23-39(18-24-19-41-21-31(48)53-30(41)10-14-45-15-12-43(27,34(24)47)37(41)45)22-46-16-11-42-26-6-3-4-8-28(26)44-33(42)25(35(49)51-2)20-40(36(42)46)13-17-52-38(39)40/h3-9,24,30,34,36-38,44H,10-23H2,1-2H3/t24-,30+,34+,36+,37+,38+,39+,40+,41+,42+,43+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 92.81000000000002
  • #RotBonds: 2
  • MW: 716.8790000000001
  • HBD: 1
  • HBA: 10
  • logP: 4.369000000000002
  • Chemical Formula: C43H48N4O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. pachysiphon Nigeria, Netherlands 403125 HXJ20171220

External Databases


References

  • Tabernaesines A-I, Cytotoxic Aspidosperma-Aspidosperma-Type Bisindole Alkaloids from Tabernaemontana pachysiphon. J Nat Prod, 2020 (PMID 33112136).

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) -5.49
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 108.72
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 14930.59
    Distribution Blood-Brain Barrier (Central Nervous System) -2.52
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.23
    Plasma Protein Binding 75.18
    Steady State Volume of Distribution 5.04
    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 Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 3.84
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -352.05
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.51
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.23
    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 Toxic
    T. Pyriformis -27100592.78
    Rat (Acute) 3.82
    Rat (Chronic Oral) 2.08
    Fathead Minnow 34209.65
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 3045016.83
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.8
    Log(P) 3.49
    Log S -4.47
    Log(Vapor Pressure) -100170.98
    Melting Point 343.12
    pKa Acid -674.84
    pKa Basic 8.47