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(CC1)\[C@]([C@]2(CO)C(OC)=O)([H])CN1CC3=C2NC4=C3C=CC=C4

  • InChI

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

  • Molecule Class: Alkaloids
  • TPSA: 65.56
  • #RotBonds: 2
  • MW: 340.423
  • HBD: 2
  • HBA: 4
  • logP: 2.3528000000000002
  • Chemical Formula: C20H24N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. dichotoma Sri Lanka, Malaysia - -
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Accumulation of indole alkaloids in a suspension culture of Tabernaemontana divaricata. Planta Med, 1988 (PMID 17265301).
  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Tertiary indole alkaloids from fruits of Tabernaemontana dichotoma. Planta Med, 1984 (PMID 6484030).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Xanthine oxidase inhibitory
    • Convulsive
    • Spasmolytic
    • Inhibitory
    • 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) -5.04
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.97
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.82
    Distribution Blood-Brain Barrier (Central Nervous System) -2.53
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.8
    Plasma Protein Binding 52.58
    Steady State Volume of Distribution 5.43
    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 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 12.35
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Safe
    Bioconcentration Factor 0.16
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.07
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.88
    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 -3.45
    Rat (Acute) 2.76
    Rat (Chronic Oral) 2.37
    Fathead Minnow 4.25
    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 422.46
    Hydration Free Energy -7.99
    Log(D) at pH=7.4 2.42
    Log(P) 2.13
    Log S -3.11
    Log(Vapor Pressure) -9.4
    Melting Point 186.87
    pKa Acid 9.72
    pKa Basic 6.43