19,20-Dehydro-10-methoxytalcarpine






Names

    • 19,20-Dehydro-10-methoxytalcarpine

Attributes

  • Canonical SMILES

    CC1=C(C=O)[C@@]2([H])C[C@]3([H])C4=C(C5=CC=C(OC)C=C5N4C)C[C@](N3C)([H])[C@@]2([H])CO1

  • InChI

    InChI=1S/C22H26N2O3/c1-12-17(10-25)15-8-21-22-16(9-20(23(21)2)18(15)11-27-12)14-6-5-13(26-4)7-19(14)24(22)3/h5-7,10,15,18,20-21H,8-9,11H2,1-4H3/t15-,18+,20-,21-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 43.7
  • #RotBonds: 2
  • MW: 366.4610000000001
  • HBD: 0
  • HBA: 5
  • logP: 3.223700000000002
  • Chemical Formula: C22H26N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. dichotoma Sri Lanka, Malaysia - -

External Databases


References

  • Vasorelaxant activity of indole alkaloids from Tabernaemontana dichotoma. J Nat Med, 2013 (PMID 22350216).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Vasorelaxant

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) -4.91
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.58
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.69
    Distribution Blood-Brain Barrier (Central Nervous System) -3.24
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.41
    Plasma Protein Binding 54.88
    Steady State Volume of Distribution 2.56
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.37
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor 1.52
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.1
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 9.33
    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 -14.97
    Rat (Acute) 2.88
    Rat (Chronic Oral) 0.56
    Fathead Minnow 4.41
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 458.22
    Hydration Free Energy -6.69
    Log(D) at pH=7.4 2.13
    Log(P) 2.86
    Log S -3.3
    Log(Vapor Pressure) -8.66
    Melting Point 183.31
    pKa Acid 7.78
    pKa Basic 7.86