Taberdivarine A






Names

    • Taberdivarine A

Attributes

  • Canonical SMILES

    OC1=C(OC)C(OC)=C(NC2=C(C(OC)=O)C[C@@]3(CC)[C@H]4[C@]25CCN4[C@H]6[C@H](OC7=C6C=C8C(NC9=C(C(OC)=O)C[C@@]%10(CC)[C@H]%11[C@]98CCN%11[C@H]%12[C@H](OC%13=C%12C=C%14C(NC%15=C(C(OC)=O)C[C@@]%16(CC)[C@H]%17[C@]%15%14CCN%17C[C@@H]%18[C@H]%16O%18)=C%13)[C@H]%10O)=C7)[C@H]3O)C5=C1

  • InChI

    InChI=1S/C65H72N6O14/c1-9-60-23-29(54(75)80-6)49-64(13-16-70(58(60)64)42-27-18-32-35(21-38(27)83-46(42)51(60)73)66-48-31(56(77)82-8)25-62(11-3)53-40(85-53)26-69-15-12-63(32,48)57(62)69)33-19-28-39(22-36(33)67-49)84-47-43(28)71-17-14-65-34-20-37(72)44(78-4)45(79-5)41(34)68-50(65)30(55(76)81-7)24-61(10-2,52(47)74)59(65)71/h18-22,40,42-43,46-47,51-53,57-59,66-68,72-74H,9-17,23-26H2,1-8H3/t40-,42-,43-,46+,47+,51-,52-,53-,57+,58+,59+,60-,61-,62-,63+,64+,65+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 234.85
  • #RotBonds: 8
  • MW: 1161.3189999999995
  • HBD: 6
  • HBA: 20
  • logP: 5.838400000000008
  • Chemical Formula: C65H72N6O14


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. officinalis China - Cai20120227

External Databases


References

  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • 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) -6.82
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 292365995077.42
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 38208799153141.05
    Distribution Blood-Brain Barrier (Central Nervous System) -1.43
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.77
    Plasma Protein Binding 55.68
    Steady State Volume of Distribution 2.57
    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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 2.89
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Safe
    Bioconcentration Factor -888649980888.01
    Biodegradation Toxic
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -362848.29
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 4.05
    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 -69347130760563940
    Rat (Acute) 18.08
    Rat (Chronic Oral) 148743533.58
    Fathead Minnow 87535976950566.06
    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 7799629714312970.0
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 -4335816504.81
    Log(P) -504736.2
    Log S -6.29
    Log(Vapor Pressure) -256837828112441.03
    Melting Point -78039567.48
    pKa Acid -1871468742001.77
    pKa Basic -15055910982.59