Taberbufamine A






Names

    • Taberbufamine A

Attributes

  • Canonical SMILES

    COC1=CC=C2NC([C@](C[C@H](C[C@H](CC)CO)C3)([H])N3CC4)=C4C2=C1

  • InChI

    InChI=1S/C20H28N2O2/c1-3-13(12-23)8-14-9-19-20-16(6-7-22(19)11-14)17-10-15(24-2)4-5-18(17)21-20/h4-5,10,13-14,19,21,23H,3,6-9,11-12H2,1-2H3/t13-,14-,19+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 48.49
  • #RotBonds: 5
  • MW: 328.4560000000001
  • HBD: 2
  • HBA: 3
  • logP: 3.5042000000000026
  • Chemical Formula: C20H28N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases


References

  • Iboga-type alkaloids with Indolizidino[8,7-b]Indole scaffold and bisindole alkaloids from Tabernaemontana bufalina Lour. Phytochemistry, 2022 (PMID 35074605).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • α-glucosidase inhibitory
    • Butyrylcholinesterase
    • Antimicrobial

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) -4.98
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.1
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.85
    Distribution Blood-Brain Barrier (Central Nervous System) -2.92
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.55
    Plasma Protein Binding 53.41
    Steady State Volume of Distribution 3.24
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.25
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.28
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.97
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 8.02
    Micronucleos Toxic
    NR-AhR Toxic
    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 -5.61
    Rat (Acute) 2.8
    Rat (Chronic Oral) 1.6
    Fathead Minnow 4.07
    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 409.38
    Hydration Free Energy -8.04
    Log(D) at pH=7.4 3.22
    Log(P) 3.15
    Log S -2.78
    Log(Vapor Pressure) -8.12
    Melting Point 145.87
    pKa Acid 13.36
    pKa Basic 7.95