3R/S-Hydroxytabernanthine






Names

    • 3R/S-Hydroxytabernanthine
    • CHEMBL518328

Attributes

  • Canonical SMILES

    CCC4C(N(C5O)CC3)[C@](CC5C4)([H])C2=C3C1=CC=C(OC)C=C1N2

  • InChI

    InChI=1S/C20H26N2O2/c1-3-11-8-12-9-16-18-15(6-7-22(19(11)16)20(12)23)14-5-4-13(24-2)10-17(14)21-18/h4-5,10-12,16,19-21,23H,3,6-9H2,1-2H3/t11?,12?,16-,19?,20?/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 48.49
  • #RotBonds: 2
  • MW: 326.44
  • HBD: 2
  • HBA: 3
  • logP: 3.2550000000000017
  • Chemical Formula: C20H26N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. calcarea Madagascar 761054 -

External Databases


References

  • New cytotoxic indole alkaloids from Tabernaemontana calcarea from the Madagascar rainforest. J Nat Prod, 2003 (PMID 12713407).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -4.86
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.08
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.01
    Distribution Blood-Brain Barrier (Central Nervous System) -3.19
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.57
    Plasma Protein Binding 32.57
    Steady State Volume of Distribution 3.08
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor 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 9.21
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.97
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.16
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.96
    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 Toxic
    T. Pyriformis -1.81
    Rat (Acute) 2.93
    Rat (Chronic Oral) 1.9
    Fathead Minnow 4.18
    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 416.7
    Hydration Free Energy -5.35
    Log(D) at pH=7.4 2.77
    Log(P) 3.35
    Log S -2.94
    Log(Vapor Pressure) -8.5
    Melting Point 209.43
    pKa Acid 11.94
    pKa Basic 7.89