Affinisine






Names

    • FS-7848
    • (+)-Affinisine
    • [(1S,12S,14R,15E)-15-ethylidene-3-methyl-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4,6,8-tetraen-13-yl]methanol
    • CHEBI:2503
    • 2912-11-0
    • Affinisine
    • Q15634128
    • C09022

Attributes

  • Canonical SMILES

    C/C=C\1/CN2[C@H]3C[C@@H]1[C@H]([C@@H]2CC4=C3N(C5=CC=CC=C45)C)CO

  • InChI

    InChI=1S/C20H24N2O/c1-3-12-10-22-18-9-15-13-6-4-5-7-17(13)21(2)20(15)19(22)8-14(12)16(18)11-23/h3-7,14,16,18-19,23H,8-11H2,1-2H3/b12-3-/t14-,16+,18-,19-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 28.4
  • #RotBonds: 1
  • MW: 308.42500000000007
  • HBD: 1
  • HBA: 3
  • logP: 3.034400000000002
  • Chemical Formula: C20H24N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. australis Brazil - ICN-68457
    T. catharinensis Brazil 403124 UEC117862
    T. contorta Cameroon 761060 N43440/HNC
    T. laeta Brazil 761076 WAG
    T. macrocarpa Indonesia 761080 -

External Databases


References

  • 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).
  • Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae). Nat Prod Res, 2021 (PMID 31274013).
  • 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).
  • Two new sarpagine-type indole alkaloids and antimalarial activity of 16-demethoxycarbonylvoacamine from Tabernaemontana macrocarpa Jack. J Nat Med, 2019 (PMID 31140017).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antiproliferative
    • Antimalarial
    • Anticolon cancer
    • Anticholinesterasic
    • Antitumor
    • Antioxidant
    • Cytotoxicity
    • Acetylbutyrylcholinesterase inhibitory
    • Scavenging
    • 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) -4.83
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.85
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.88
    Distribution Blood-Brain Barrier (Central Nervous System) -2.51
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.73
    Plasma Protein Binding 64.86
    Steady State Volume of Distribution 2.92
    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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.64
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor 0.35
    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 5.61
    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 -0.52
    Rat (Acute) 3.09
    Rat (Chronic Oral) 1.78
    Fathead Minnow 4.33
    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 435.75
    Hydration Free Energy -5.07
    Log(D) at pH=7.4 1.98
    Log(P) 3.0
    Log S -2.91
    Log(Vapor Pressure) -8.25
    Melting Point 198.91
    pKa Acid 10.58
    pKa Basic 8.56