19,20-(E)-Vallesamine






Names

    • DA-59905
    • Vallesamine
    • CHEMBL5177009
    • AKOS040760956
    • FS-9766
    • (5S)-4-[(E)-Ethylidene]-1,3,4,5,6,7-hexahydro-6-hydroxymethyl-2alpha,5-ethano-2H-azocino[4,3-b]indole-6beta-carboxylic acid methyl ester
    • 3368-87-4
    • methyl (12S,13S,14E)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.03,11.04,9]heptadeca-3(11),4,6,8-tetraene-12-carboxylate
    • 19,20-(E)-Vallesamine
    • DTXSID601318157

Attributes

  • Canonical SMILES

    C/C=C\1/CN2CC[C@@H]1[C@](C3=C(C2)C4=CC=CC=C4N3)(CO)C(=O)OC

  • InChI

    InChI=1S/C20H24N2O3/c1-3-13-10-22-9-8-16(13)20(12-23,19(24)25-2)18-15(11-22)14-6-4-5-7-17(14)21-18/h3-7,16,21,23H,8-12H2,1-2H3/b13-3-/t16-,20-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 65.56
  • #RotBonds: 2
  • MW: 340.4230000000001
  • HBD: 2
  • HBA: 4
  • logP: 2.3528000000000002
  • Chemical Formula: C20H24N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).
  • New Iboga-Type Indole Alkaloids from Tabernaemontana divaricata. Nat Prod Bioprospect, 2019 (PMID 31724098).

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) -5.06
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.88
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.89
    Distribution Blood-Brain Barrier (Central Nervous System) -2.71
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.61
    Plasma Protein Binding 51.7
    Steady State Volume of Distribution 7.41
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor 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 9.32
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Safe
    Bioconcentration Factor -0.53
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.28
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.69
    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 -2.75
    Rat (Acute) 3.05
    Rat (Chronic Oral) 2.45
    Fathead Minnow 4.51
    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 405.52
    Hydration Free Energy -7.14
    Log(D) at pH=7.4 2.46
    Log(P) 2.22
    Log S -3.19
    Log(Vapor Pressure) -8.45
    Melting Point 164.63
    pKa Acid 9.1
    pKa Basic 7.72