Voachalotine






Names

    • NSC-180537
    • 664-25-5
    • NSC180537
    • Sarpagan-16-carboxylic acid, methyl ester, (16R)-
    • methyl (12R,14R,15E)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4,6,8-tetraene-13-carboxylate
    • Voachalotine
    • Methyl (1S,12S,13R,14S,15E)-15-ethylidene-13-(hydroxymethyl)-3-methyl-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4,6,8-tetraene-13-carboxylate

Attributes

  • Canonical SMILES

    C/C=C\1/CN2[C@@H]3CC4=C(C2C[C@H]1C3(CO)C(=O)OC)N(C5=CC=CC=C45)C

  • InChI

    InChI=1S/C22H26N2O3/c1-4-13-11-24-18-10-16(13)22(12-25,21(26)27-3)19(24)9-15-14-7-5-6-8-17(14)23(2)20(15)18/h4-8,16,18-19,25H,9-12H2,1-3H3/b13-4-/t16-,18?,19-,22?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 54.699999999999996
  • #RotBonds: 2
  • MW: 366.46100000000007
  • HBD: 1
  • HBA: 5
  • logP: 2.5776000000000012
  • Chemical Formula: C22H26N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. australis Brazil - ICN-68457
    T. bufalina China 403123 Cai20170220
    T. catharinensis Brazil 403124 UEC117862
    T. laeta Brazil 761076 WAG

External Databases


References

  • Application of preparative high-speed counter-current chromatography for the separation of two alkaloids from the roots of Tabernaemontana catharinensis (Apocynaceae). Molecules, 2011 (PMID 21892126).
  • Bio-guided search of active indole alkaloids from Tabernaemontana catharinensis: Antitumour activity, toxicity in silico and molecular modelling studies. Bioorg Chem, 2019 (PMID 30599414).
  • Chemical constituents antioxidant and anticholinesterasic activity of Tabernaemontana catharinensis. ScientificWorldJournal, 2013 (PMID 23983637).
  • Chemical Constituents from Tabernaemontana bufalina Lour. Chem Biodivers, 2019 (PMID 30411487).
  • Chromatographic analysis and antioxidant capacity of Tabernaemontana catharinensis. Nat Prod Commun, 2014 (PMID 24660464).
  • Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme. Bioorg Med Chem, 2005 (PMID 15911323).
  • In vitro antiproliferative activity of alkaloids isolated from Tabernaemontana catharinensis A.DC (Apocynaceae). Nat Prod Res, 2022 (PMID 35075954).
  • Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures. An Acad Bras Cienc, 2008 (PMID 18797794).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimycobacterial
    • Anticrotalic
    • Antitumoral
    • Antiproliferative
    • Anticholinesterasic
    • Antitumor
    • Antiinflammatory
    • Analgesic
    • Antileishmanial
    • Antioxidant
    • Cytotoxicity
    • Acetylbutyrylcholinesterase inhibitory
    • Scavenging
    • Trypanocidal
    • 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) -4.84
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.84
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.53
    Distribution Blood-Brain Barrier (Central Nervous System) -2.72
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.92
    Plasma Protein Binding 50.7
    Steady State Volume of Distribution 6.05
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 6.58
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -0.1
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.01
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.93
    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 -12.46
    Rat (Acute) 3.33
    Rat (Chronic Oral) 1.91
    Fathead Minnow 4.82
    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 464.87
    Hydration Free Energy -5.0
    Log(D) at pH=7.4 2.38
    Log(P) 2.55
    Log S -2.91
    Log(Vapor Pressure) -8.57
    Melting Point 184.41
    pKa Acid 7.91
    pKa Basic 7.72