19(S)-Hydroxyibogamine






Names

    • 19(S)-Hydroxyibogamine

Attributes

  • Canonical SMILES

    C[C@@](O)([H])[C@]4([H])[C@@](N(C5)CC3)([H])[C@](C[C@]5([H])C4)([H])C1=C3C(C=CC=C2)=C2N1

  • InChI

    InChI=1S/C19H24N2O/c1-11(22)15-8-12-9-16-18-14(6-7-21(10-12)19(15)16)13-4-2-3-5-17(13)20-18/h2-5,11-12,15-16,19-20,22H,6-10H2,1H3/t11-,12-,15+,16-,19-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 39.26
  • #RotBonds: 1
  • MW: 296.414
  • HBD: 2
  • HBA: 2
  • logP: 2.8988000000000005
  • Chemical Formula: C19H24N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Five new iboga alkaloids from Tabernaemontana corymbosa. J Nat Prod, 2002 (PMID 12027738).
  • 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) -5.09
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.05
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.83
    Distribution Blood-Brain Barrier (Central Nervous System) -2.97
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.41
    Plasma Protein Binding 69.59
    Steady State Volume of Distribution 3.95
    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 10.05
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.53
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.43
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.94
    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 -1.9
    Rat (Acute) 3.07
    Rat (Chronic Oral) 1.94
    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 387.26
    Hydration Free Energy -5.83
    Log(D) at pH=7.4 2.1
    Log(P) 1.97
    Log S -2.67
    Log(Vapor Pressure) -7.94
    Melting Point 212.89
    pKa Acid 11.54
    pKa Basic 7.92