3-Oxotabersonine






Names

    • 18,19-DIDEHYDRO-3-OXOTABERSONINE
    • 3-Oxotabersonine
    • NFSOHPSLANPOGJ-UHFFFAOYSA-N

Attributes

  • Canonical SMILES

    CC[C@@]12CC(C(OC)=O)=C3[C@@]4(C5=CC=CC=C5N3)[C@]1([H])N(C(C=C2)=O)CC4

  • InChI

    InChI=1S/C21H22N2O3/c1-3-20-9-8-16(24)23-11-10-21(19(20)23)14-6-4-5-7-15(14)22-17(21)13(12-20)18(25)26-2/h4-9,19,22H,3,10-12H2,1-2H3/t19-,20-,21-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 58.64
  • #RotBonds: 2
  • MW: 350.4180000000001
  • HBD: 1
  • HBA: 4
  • logP: 2.7478000000000007
  • Chemical Formula: C21H22N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604
    T. cymosa Colombia 761066 JBC3243

External Databases


References

  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Molecular Human Targets of Bioactive Alkaloid-Type Compounds from Tabernaemontana cymose Jacq. Molecules, 2021 (PMID 34205626).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticancer
    • Antiinflammatory
    • Antioxidant
    • 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) -4.84
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.67
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.45
    Distribution Blood-Brain Barrier (Central Nervous System) -2.31
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.96
    Plasma Protein Binding 61.21
    Steady State Volume of Distribution 3.2
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor 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 6.84
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.12
    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 Safe
    Daphnia Maga 4.48
    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 -8.87
    Rat (Acute) 3.36
    Rat (Chronic Oral) 2.24
    Fathead Minnow 3.98
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 428.29
    Hydration Free Energy -7.62
    Log(D) at pH=7.4 2.89
    Log(P) 2.55
    Log S -3.75
    Log(Vapor Pressure) -7.95
    Melting Point 212.01
    pKa Acid 9.03
    pKa Basic 6.52