Desethyl-voacangine






Names

    • 3-hydroxy-isovoacangine
    • CHEMBL479871
    • Desethyl-voacangine

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@H]2C[C@]3(C(OC)=O)[C@H]1[N@@](CCC4=C3NC5=C4C=CC(OC)=C5)C2O

  • InChI

    InChI=1S/C22H28N2O4/c1-4-12-9-13-11-22(21(26)28-3)18-16(7-8-24(19(12)22)20(13)25)15-6-5-14(27-2)10-17(15)23-18/h5-6,10,12-13,19-20,23,25H,4,7-9,11H2,1-3H3/t12-,13-,19-,20?,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 74.79
  • #RotBonds: 3
  • MW: 384.4760000000001
  • HBD: 2
  • HBA: 5
  • logP: 2.5822000000000007
  • Chemical Formula: C22H28N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. australis Brazil - ICN-68457
    T. chippii Ivory Coast - Lg12291

External Databases


References

  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme. Bioorg Med Chem, 2005 (PMID 15911323).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimicrobial
    • Anticholinesterase

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) -4.96
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.04
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.67
    Distribution Blood-Brain Barrier (Central Nervous System) -3.26
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.85
    Plasma Protein Binding 53.58
    Steady State Volume of Distribution 4.54
    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 Non-Inhibitor
    CYP 2C9 Substrate 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 9.44
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.14
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.38
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 8.58
    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 -23.92
    Rat (Acute) 3.08
    Rat (Chronic Oral) 2.08
    Fathead Minnow 4.12
    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 442.89
    Hydration Free Energy -5.61
    Log(D) at pH=7.4 2.67
    Log(P) 2.69
    Log S -3.3
    Log(Vapor Pressure) -9.0
    Melting Point 214.1
    pKa Acid 9.14
    pKa Basic 7.14