Tabernabovine B






Names

    • Tabernabovine B

Attributes

  • Canonical SMILES

    O[C@@]12[C@@](N3CC2)(CC4)C([C@@H]5[C@@]4(CC)[C@H](O)[C@H]3CO5)C6=C(OC)C=CC=C61

  • InChI

    InChI=1S/C21H27NO4/c1-3-19-7-8-20-16-15-12(5-4-6-14(15)25-2)21(20,24)9-10-22(20)13(17(19)23)11-26-18(16)19/h4-6,13,16-18,23-24H,3,7-11H2,1-2H3/t13-,16?,17-,18-,19-,20-,21-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.16000000000001
  • #RotBonds: 2
  • MW: 357.4500000000001
  • HBD: 2
  • HBA: 5
  • logP: 1.7565999999999997
  • Chemical Formula: C21H27NO4


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

  • No relationship found

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) -4.75
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.82
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.92
    Distribution Blood-Brain Barrier (Central Nervous System) -3.3
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.46
    Plasma Protein Binding 42.43
    Steady State Volume of Distribution 2.72
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 7.45
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.26
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.82
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.57
    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 -10.3
    Rat (Acute) 3.22
    Rat (Chronic Oral) 2.12
    Fathead Minnow 3.95
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 412.32
    Hydration Free Energy -7.3
    Log(D) at pH=7.4 1.55
    Log(P) 1.28
    Log S -2.46
    Log(Vapor Pressure) -9.75
    Melting Point 219.25
    pKa Acid 10.06
    pKa Basic 7.71