Tabernaelegantine D






Names

    • Tabernaelegantine D

Attributes

  • Canonical SMILES

    CC[C@@H]1[C@H]5C[C@H]([C@]2=C(OC)C=C6C(C(CCN(C9)C8C(C(OC)=O)7C[C@@H]9C[C@@H]8CC)=C7N6)=C2)C(NC4=CC=CC=C34)=C3C[C@@H]([C@@H]5C(OC)=O)N(C)C1

  • InChI

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

  • Molecule Class: Alkaloids
  • TPSA: 99.89
  • #RotBonds: 6
  • MW: 706.928
  • HBD: 2
  • HBA: 7
  • logP: 6.568800000000007
  • Chemical Formula: C43H54N4O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM
    T. officinalis China - Cai20120227

External Databases


References

  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Vobasinyl-Iboga Alkaloids from Tabernaemontana elegans: Cell Cycle Arrest and Apoptosis-Inducing Activity in HCT116 Colon Cancer Cells. J Nat Prod, 2016 (PMID 27704811).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -5.75
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 17.55
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 3028.37
    Distribution Blood-Brain Barrier (Central Nervous System) -2.76
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.23
    Plasma Protein Binding 81.59
    Steady State Volume of Distribution 5.52
    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 12.78
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -73.6
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.56
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 6.31
    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 -5496102.2
    Rat (Acute) 2.91
    Rat (Chronic Oral) 2.43
    Fathead Minnow 6940.97
    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 614800.76
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 6.03
    Log(P) 5.91
    Log S -5.59
    Log(Vapor Pressure) -20179.54
    Melting Point 290.16
    pKa Acid -108.72
    pKa Basic 7.01