Apparicine






Names

    • CHEMBL285671
    • Q27105225
    • (13S,14E)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.03,11.04,9]heptadeca-3(11),4,6,8-tetraene
    • DTXSID30415108
    • BDBM50593481
    • Apparicine
    • AKOS040735348
    • CHEBI:78
    • C09036
    • 2122-36-3
    • (-)-Apparicine
    • SCHEMBL22836776
    • [5S,4E,(-)]-4-Ethylidene-1,3,4,5,6,7-hexahydro-6-methylene-2alpha,5-ethano-2H-azocino[4,3-b]indole

Attributes

  • Canonical SMILES

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

  • InChI

    InChI=1S/C18H20N2/c1-3-13-10-20-9-8-14(13)12(2)18-16(11-20)15-6-4-5-7-17(15)19-18/h3-7,14,19H,2,8-11H2,1H3/b13-3-/t14-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 19.03
  • #RotBonds: 0
  • MW: 264.37199999999996
  • HBD: 1
  • HBA: 1
  • logP: 3.962900000000003
  • Chemical Formula: C18H20N2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. alba Mexico 761051 132793, 133359, 161424 to 161427
    T. arborea Mexico, Costa Rica 681494 132793, 133359, 161424 to 161427
    T. bufalina China 403123 Cai20170220
    T. chippii Ivory Coast - Lg12291
    T. dichotoma Sri Lanka, Malaysia - -
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM
    T. officinalis China - Cai20120227
    T. pachysiphon Nigeria, Netherlands 403125 HXJ20171220

External Databases


References

  • Characterization of a Suspension Culture of Tabernaemontana elegans on Growth, Nutrient Uptake, and Accumulation of Indole Alkaloids*. Planta Med, 1989 (PMID 17262332).
  • Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata. J Nat Prod, 2018 (PMID 30169038).
  • Taberdines L and M, two new alkaloids from Tabernaemontana divaricata. Nat Prod Res, 2022 (PMID 34933610).
  • Isolation of opioid-active compounds from Tabernaemontana pachysiphon leaves. J Pharm Pharmacol, 1999 (PMID 10678501).
  • Tertiary indole alkaloids from fruits of Tabernaemontana dichotoma. Planta Med, 1984 (PMID 6484030).
  • Quantification of Anti-Addictive Alkaloids Ibogaine and Voacangine in In Vivo- and In Vitro-Grown Plants of Two Mexican Tabernaemontana Species. Chem Biodivers, 2016 (PMID 27448833).
  • Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata. Molecules, 2023 (PMID 37764440).
  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Tertiary indole alkaloids from leaves of Tabernaemontana dichotoma. Planta Med, 1983 (PMID 17404903).
  • Virtual Screening of compounds from Tabernaemontana divaricata for potential anti-bacterial activity. Bioinformation, 2014 (PMID 24748755).
  • Antimycobacterial Activity of Alkaloids and Extracts from Tabernaemontana alba and T. arborea. Planta Med, 2022 (PMID 32392600).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Accumulation of indole alkaloids in a suspension culture of Tabernaemontana divaricata. Planta Med, 1988 (PMID 17265301).
  • Dichomine, a novel type of iboga alkaloid*,**. Planta Med, 1983 (PMID 17405059).

Compound-Protein Relationships


Compound Activities

    • Antibacterial
    • Antimycobacterial
    • Antiproliferative
    • Xanthine oxidase inhibitory
    • Convulsive
    • Analgesic
    • Spasmolytic
    • Inhibitory
    • Antiaddictive
    • Antimicrobial
    • 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) -4.68
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.79
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.95
    Distribution Blood-Brain Barrier (Central Nervous System) -2.57
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.83
    Plasma Protein Binding 53.17
    Steady State Volume of Distribution 3.91
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 8.06
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Safe
    Bioconcentration Factor 1.08
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.95
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.38
    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 0.66
    Rat (Acute) 2.99
    Rat (Chronic Oral) 2.03
    Fathead Minnow 4.72
    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 358.61
    Hydration Free Energy -6.9
    Log(D) at pH=7.4 2.9
    Log(P) 3.91
    Log S -3.59
    Log(Vapor Pressure) -6.92
    Melting Point 160.19
    pKa Acid 12.28
    pKa Basic 7.8