Tabernaelegantine A






Names

    • MLS000728618
    • CHEMBL1518309
    • Tabernaelegantine A
    • HMS2271O10
    • SMR000470798

Attributes

  • Canonical SMILES

    CC[C@H]1CC2CC3(C1N(C2)CCC4=C3NC5=C4C=CC(=C5[C@H]6C[C@H]7[C@@H](CN([C@H]([C@H]7C(=O)OC)CC8=C6NC9=CC=CC=C89)C)CC)OC)C(=O)OC

  • InChI

    InChI=1S/C43H54N4O5/c1-7-24-17-23-20-43(42(49)52-6)39-28(15-16-47(21-23)40(24)43)27-13-14-34(50-4)36(38(27)45-39)31-18-29-25(8-2)22-46(3)33(35(29)41(48)51-5)19-30-26-11-9-10-12-32(26)44-37(30)31/h9-14,23-25,29,31,33,35,40,44-45H,7-8,15-22H2,1-6H3/t23?,24-,25+,29-,31+,33-,35-,40?,43?/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 99.89000000000003
  • #RotBonds: 6
  • MW: 706.9280000000002
  • HBD: 2
  • HBA: 7
  • logP: 6.568800000000007
  • Chemical Formula: C43H54N4O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM

External Databases


References

  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).
  • Vobasinyl-Iboga Alkaloids from Tabernaemontana elegans: Cell Cycle Arrest and Apoptosis-Inducing Activity in HCT116 Colon Cancer Cells. J Nat Prod, 2016 (PMID 27704811).
  • Vobasinyl-iboga bisindole alkaloids, potent acetylcholinesterase inhibitors from Tabernaemontana divaricata root. J Pharm Pharmacol, 2006 (PMID 16734986).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antiinflammatory
    • Cytotoxicity
    • Cholinesterase
    • Acetylcholinesterase 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) -5.71
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 18.05
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 3098.69
    Distribution Blood-Brain Barrier (Central Nervous System) -2.81
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.26
    Plasma Protein Binding 79.09
    Steady State Volume of Distribution 5.16
    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 Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 12.57
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -75.22
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.41
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 5.63
    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 -5623547.18
    Rat (Acute) 2.95
    Rat (Chronic Oral) 2.4
    Fathead Minnow 7101.73
    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 629200.33
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 6.04
    Log(P) 6.35
    Log S -5.57
    Log(Vapor Pressure) -20654.15
    Melting Point 284.58
    pKa Acid -112.06
    pKa Basic 6.3