Vobtusine lactone






Names

    • DTXCID60257957
    • NSC-180538
    • "21'-oxovobtusine", 'DTXSID80306830
    • 19772-81-7', "methyl 24'-hydroxy-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 24'-hydroxy-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", 'NSC180538
    • Vobtusine lactone

Attributes

  • Canonical SMILES

    [H][C@]12[C@]34CC(C(OC)=O)=C5NC6=CC=CC=C6[C@@]51CCN2C([H])[C@]7(C[C@@](C[C@@]([C@@H]8CCN9CC%10)(CC(O8)=O)[C@@]9([H])[C@@]%11%10C%12=C%13C(OC)=CC=C%12)([H])[C@]%11(O)N%13C7)[C@@H]3OCC4

  • InChI

    InChI=1S/C43H48N4O7/c1-51-29-9-5-7-27-32(29)47-23-38(18-24-19-40-21-31(48)54-30(40)10-14-45-16-12-42(27,36(40)45)43(24,47)50)22-46-15-11-41-26-6-3-4-8-28(26)44-33(41)25(34(49)52-2)20-39(35(41)46)13-17-53-37(38)39/h3-9,24,30,35-37,44,50H,10-23H2,1-2H3/t24-,30+,35+,36+,37+,38+,39+,40+,41+,42-,43-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 113.04000000000002
  • #RotBonds: 2
  • MW: 732.8780000000002
  • HBD: 2
  • HBA: 11
  • logP: 3.6890000000000027
  • Chemical Formula: C43H48N4O7


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. pachysiphon Nigeria, Netherlands 403125 HXJ20171220
    T. sphaerocarpa Indonesia 761099 AP070902

External Databases


References

  • Biscarpamontamines A and B, an aspidosperma-iboga bisindole alkaloid and an aspidosperma-aspidosperma bisindole alkaloid, from Tabernaemontana sphaerocarpa. J Nat Prod, 2009 (PMID 19711971).
  • 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) -5.83
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 155.65
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 21080.57
    Distribution Blood-Brain Barrier (Central Nervous System) -2.77
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.05
    Plasma Protein Binding 74.71
    Steady State Volume of Distribution 4.57
    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 3.05
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -493.95
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.38
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.61
    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 -38261879.17
    Rat (Acute) 3.34
    Rat (Chronic Oral) 2.22
    Fathead Minnow 48298.71
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 4300094.57
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.48
    Log(P) 2.75
    Log S -4.52
    Log(Vapor Pressure) -141497.19
    Melting Point 371.91
    pKa Acid -975.3
    pKa Basic 8.95