Apocidine A






Names

    • Apocidine A

Attributes

  • Canonical SMILES

    COC(=O)C1=C2[C@]3(CCN4[C@H]3[C@@]5(C1)CCO[C@]5(CC4)O)C6=CC=CC=C6N2

  • InChI

    InChI=1S/C21H24N2O4/c1-26-17(24)13-12-19-8-11-27-21(19,25)7-10-23-9-6-20(18(19)23)14-4-2-3-5-15(14)22-16(13)20/h2-5,18,22,25H,6-12H2,1H3/t18-,19-,20-,21-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 71.03
  • #RotBonds: 1
  • MW: 368.43300000000005
  • HBD: 2
  • HBA: 6
  • logP: 1.754
  • Chemical Formula: C21H24N2O4


Species

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

External Databases


References

  • Ibogan, Aspidosperman, Vincamine, and Bisindole Alkaloids from a Malayan Tabernaemontana corymbosa: Iboga Alkaloids with C-20α Substitution. J Nat Prod, 2016 (PMID 27077800).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Growth 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) -5.15
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.08
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.15
    Distribution Blood-Brain Barrier (Central Nervous System) -2.72
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.69
    Plasma Protein Binding 40.76
    Steady State Volume of Distribution 4.04
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 5.86
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.99
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.95
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.39
    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 -22.31
    Rat (Acute) 3.21
    Rat (Chronic Oral) 2.31
    Fathead Minnow 4.08
    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 419.91
    Hydration Free Energy -6.01
    Log(D) at pH=7.4 2.09
    Log(P) 1.35
    Log S -2.27
    Log(Vapor Pressure) -8.87
    Melting Point 215.77
    pKa Acid 6.43
    pKa Basic 6.54