Taberdivarine H






Names

    • (13E,14S,16S,18R)-13-ethylidene-11-methyl-1-aza-11-azoniapentacyclo[12.3.1.02,7.08,17.011,16]octadeca-2,4,6,8(17)-tetraene-18-carboxylate
    • Taberdivarine H
    • 1662688-34-7

Attributes

  • Canonical SMILES

    COC1=C(O)C=C2C(NC3=C(C(OC)=O)C[C@@]4(CC)[C@H]5[C@]32CCN5[C@H](C6=C(OC)C=C(NC7=C(C(OC)=O)C[C@@]8(CC)[C@H]9[C@]7%10CCN9C=CC8)C%10=C6)[C@@H]%11[C@H]4O%11)=C1OC

  • InChI

    InChI=1S/C45H52N4O9/c1-8-42-11-10-14-48-15-12-44(40(42)48)25-17-22(29(53-3)19-27(25)46-35(44)23(20-42)38(51)56-6)31-34-37(58-34)43(9-2)21-24(39(52)57-7)36-45(13-16-49(31)41(43)45)26-18-28(50)32(54-4)33(55-5)30(26)47-36/h10,14,17-19,31,34,37,40-41,46-47,50H,8-9,11-13,15-16,20-21H2,1-7H3/t31-,34-,37-,40+,41+,42+,43-,44+,45+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 143.58999999999997
  • #RotBonds: 8
  • MW: 792.9299999999997
  • HBD: 3
  • HBA: 13
  • logP: 5.787300000000006
  • Chemical Formula: C45H52N4O9


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases

    • PubChem CID: 134715098
    • CAS RN: 1662688-34-7

References

  • New Iboga-Type Indole Alkaloids from Tabernaemontana divaricata. Nat Prod Bioprospect, 2019 (PMID 31724098).
  • Trimeric and dimeric Aspidosperma-type alkaloids from leaves of Tabernaemontana divaricata 'Dwaft'. Bioorg Chem, 2021 (PMID 34500306).

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) -5.27
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 428.61
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 56779.64
    Distribution Blood-Brain Barrier (Central Nervous System) -3.23
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.75
    Plasma Protein Binding 52.21
    Steady State Volume of Distribution 2.54
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-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 Non-Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 7.82
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -1321.6
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.97
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 4.16
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Toxic
    T. Pyriformis -103054672.17
    Rat (Acute) 2.49
    Rat (Chronic Oral) 2.72
    Fathead Minnow 130088.73
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Toxic
    General Properties Boiling Point 11586292.79
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.47
    Log(P) 4.73
    Log S -5.18
    Log(Vapor Pressure) -381454.29
    Melting Point 241.57
    pKa Acid -2726.78
    pKa Basic 8.36