Tabernamine






Names

    • NSC-265471
    • Tabernamine
    • NSC265471
    • TABERNAMINE
    • Q15427840

Attributes

  • Canonical SMILES

    CC[C@@H]1C[C@]2([H])C[C@@]3([H])[C@]1([H])N(CCC4=C3NC5=C4C=CC([C@@H]6C[C@]7([H])[C@@H](C(OC)=O)[C@](N(C)C/C7=C/C)([H])CC8=C6NC9=CC=CC=C89)=C5)C2([H])[H]

  • InChI

    InChI=1S/C40H48N4O2/c1-5-23-15-22-16-32-37-28(13-14-44(20-22)39(23)32)27-12-11-25(17-34(27)42-37)30-18-29-24(6-2)21-43(3)35(36(29)40(45)46-4)19-31-26-9-7-8-10-33(26)41-38(30)31/h6-12,17,22-23,29-30,32,35-36,39,41-42H,5,13-16,18-21H2,1-4H3/b24-6-/t22-,23-,29+,30+,32-,35+,36-,39-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 64.36
  • #RotBonds: 3
  • MW: 616.8500000000003
  • HBD: 2
  • HBA: 4
  • logP: 7.153100000000008
  • Chemical Formula: C40H48N4O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. chippii Ivory Coast - Lg12291
    T. corymbosa Malaysia, China 1679252 GK604
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. johnstonii Kenya - -
    T. laeta Brazil 761076 WAG

External Databases


References

  • A new natural auaternary indole alkaloid isolated from Tabernaemontana laeta Mart. (Apocynaceae) Journal of the Brazilian Chemical Society, 2001 (DOI).
  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata. J Nat Prod, 2018 (PMID 30169038).
  • Ibogan, Aspidosperman, Vincamine, and Bisindole Alkaloids from a Malayan Tabernaemontana corymbosa: Iboga Alkaloids with C-20α Substitution. J Nat Prod, 2016 (PMID 27077800).
  • Iboga-type alkaloids with Indolizidino[8,7-b]Indole scaffold and bisindole alkaloids from Tabernaemontana bufalina Lour. Phytochemistry, 2022 (PMID 35074605).
  • Plant anticancer agents V: new bisindole alkaloids from Tabernaemontana johnstonii stem bark. J Pharm Sci, 1978 (PMID 621649).
  • 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

    • Anticancer
    • Reproducible
    • Antiproliferative
    • Antileukemic
    • α-glucosidase inhibitory
    • Antimicrobial
    • Cytotoxicity
    • Acetylbutyrylcholinesterase inhibitory
    • Butyrylcholinesterase
    • Growth 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) -5.8
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -3.93
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 213.34
    Distribution Blood-Brain Barrier (Central Nervous System) -3.12
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.64
    Plasma Protein Binding 101.77
    Steady State Volume of Distribution 5.38
    Metabolism Breast Cancer Resistance Protein 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 Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 12.08
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.46
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.09
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.12
    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 -385622.95
    Rat (Acute) 2.94
    Rat (Chronic Oral) 2.25
    Fathead Minnow 492.19
    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 39734.14
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.47
    Log(P) 6.15
    Log S -5.83
    Log(Vapor Pressure) -1288.47
    Melting Point 304.94
    pKa Acid 6.74
    pKa Basic 6.79