Vallesiachotamine






Names

    • NSC-338699
    • VALLESIACHOTAMINE K106
    • FS-7866
    • NSC338699
    • CHEMBL454571
    • (2S,12betaS)-methyl 2-((1E)-1-formyl-1-propenyl)-1,2,6,7,12,12b-hexahydroindolo(2,3-alpha)quinolizine-3-carboxylic acid
    • (15S,16E)-16,17,20,21-Tetradehydro-16-formyl-18,19-secoyohimban-19-oic acid methyl ester
    • methyl (2S,12bS)-2-[(E)-1-oxobut-2-en-2-yl]-1,2,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine-3-carboxylate
    • methyl (2S,12bS)-2-((E)-1-oxobut-2-en-2-yl)-1,2,6,7,12,12b-hexahydroindolo(2,3-a)quinolizine-3-carboxylate
    • 5523-37-5
    • SCHEMBL20943621
    • (2S,12betaS)-methyl 2-[(1E)-1-formyl-1-propenyl]-1,2,6,7,12,12b-hexahydroindolo[2,3-alpha]quinolizine- 3-carboxylic acid
    • (2S,12betaS)-methyl 2-[(1E)-1-formyl-1-propenyl]-1,2,6,7,12,12b-hexahydroindolo[2,3-alpha]quinolizine-3-carboxylic acid
    • Vallesiachotamine

Attributes

  • Canonical SMILES

    C/C=C([C@@]1([H])C[C@]2([H])C3=C(C4=CC=CC=C4N3)CCN2C=C1C(OC)=O)/C=O

  • InChI

    InChI=1S/C21H22N2O3/c1-3-13(12-24)16-10-19-20-15(14-6-4-5-7-18(14)22-20)8-9-23(19)11-17(16)21(25)26-2/h3-7,11-12,16,19,22H,8-10H2,1-2H3/b13-3-/t16-,19-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.4
  • #RotBonds: 3
  • MW: 350.4180000000001
  • HBD: 1
  • HBA: 4
  • logP: 3.2891000000000012
  • Chemical Formula: C21H22N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. corymbosa Malaysia, China 1679252 GK604
    T. psorocarpa Ghana, Ivory Coast 761091 8134

External Databases


References

  • Alkaloids from Tabernaemontana psorocarpa. Planta Med, 1983 (PMID 17405098).
  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).

Compound-Protein Relationships


Compound Activities

    • Inhibitory
    • Cytotoxicity
    • Xanthine oxidase inhibitory

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) -4.99
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.71
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.54
    Distribution Blood-Brain Barrier (Central Nervous System) -2.27
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.66
    Plasma Protein Binding 51.08
    Steady State Volume of Distribution 2.25
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate 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 Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.06
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Safe
    Bioconcentration Factor 0.55
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.66
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.82
    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 Toxic
    T. Pyriformis -6.22
    Rat (Acute) 3.33
    Rat (Chronic Oral) 1.83
    Fathead Minnow 4.8
    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 451.89
    Hydration Free Energy -5.66
    Log(D) at pH=7.4 3.09
    Log(P) 3.28
    Log S -4.17
    Log(Vapor Pressure) -8.9
    Melting Point 164.15
    pKa Acid 8.92
    pKa Basic 6.5