Tabernabovine A






Names

    • Tabernabovine A

Attributes

  • Canonical SMILES

    O[C@](CCN1C=C2[C@@H]3C[C@H](NCC4)C5=C4C6=CC=CC=C6N5[C@@H]3C(OC)=O)(C7=C8C=CC=C7)[C@@]1([H])N8[C@@H]2C

  • InChI

    InChI=1S/C30H32N4O3/c1-17-21(16-32-14-12-30(36)22-8-4-6-10-25(22)33(17)29(30)32)20-15-23-26-19(11-13-31-23)18-7-3-5-9-24(18)34(26)27(20)28(35)37-2/h3-10,16-17,20,23,27,29,31,36H,11-15H2,1-2H3/t17-,20+,23+,27+,29-,30-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 69.96999999999998
  • #RotBonds: 2
  • MW: 496.6110000000002
  • HBD: 2
  • HBA: 7
  • logP: 3.5877000000000026
  • Chemical Formula: C30H32N4O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bovina China, Vietnam 3036760 Cai20150423

External Databases


References

  • Tabernabovines A-C: Three Monoterpenoid Indole Alkaloids from the Leaves of Tabernaemontana bovina. Org Lett, 2019 (PMID 31294995).

Compound-Protein Relationships


Compound Activities

    • Inhibitory

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) -5.55
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.94
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 0.11
    Distribution Blood-Brain Barrier (Central Nervous System) -2.2
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 1.17
    Plasma Protein Binding 73.23
    Steady State Volume of Distribution 6.55
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.3
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.2
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.17
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 8.57
    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 -4444.62
    Rat (Acute) 3.23
    Rat (Chronic Oral) 1.7
    Fathead Minnow 14.09
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Safe
    General Properties Boiling Point 428.88
    Hydration Free Energy -2.85
    Log(D) at pH=7.4 3.23
    Log(P) 2.82
    Log S -3.81
    Log(Vapor Pressure) -7.74
    Melting Point 201.37
    pKa Acid 9.0
    pKa Basic 8.2