Taberdivarine B






Names

    • Taberdivarine B

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](C6=C(C=C(NC7=C(C(OC)=O)C[C@@]8(CC)[C@H]9[C@]7%10CCN9[C@H]%11[C@H](OC%12=C%11C=C%13C(NC%14=C(C(OC)=O)C[C@@]%15(CC)[C@H]%16[C@]%14%13CCN%16CC=C%15)=C%12)[C@H]8O)C%10=C6)OC)[C@@H]%17[C@H]3O%17)C5=C1

  • InChI

    InChI=1S/C66H74N6O13/c1-10-61-14-13-18-70-19-15-64(58(61)70)35-23-31-42(26-39(35)68-50(64)32(27-61)55(75)81-7)84-48-44(31)71-20-16-65-36-22-30(41(78-4)25-38(36)67-51(65)33(56(76)82-8)28-62(11-2,53(48)74)59(65)71)45-49-54(85-49)63(12-3)29-34(57(77)83-9)52-66(17-21-72(45)60(63)66)37-24-40(73)46(79-5)47(80-6)43(37)69-52/h13-14,22-26,44-45,48-49,53-54,58-60,67-69,73-74H,10-12,15-21,27-29H2,1-9H3/t44-,45-,48+,49-,53-,54-,58+,59+,60+,61+,62-,63-,64+,65+,66+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 214.61999999999998
  • #RotBonds: 10
  • MW: 1159.346999999999
  • HBD: 5
  • HBA: 19
  • logP: 7.28130000000001
  • Chemical Formula: C66H74N6O13


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. officinalis China - Cai20120227

External Databases


References

  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • 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) -6.8
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 450080590700.51
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 58820234997194.766
    Distribution Blood-Brain Barrier (Central Nervous System) -1.43
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.7
    Plasma Protein Binding 53.33
    Steady State Volume of Distribution 2.39
    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 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 3.6
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Safe
    Bioconcentration Factor -1368025366254.04
    Biodegradation Toxic
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -558582.89
    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 -106755889298481840
    Rat (Acute) 42.11
    Rat (Chronic Oral) 228982077.66
    Fathead Minnow 134756496686954.4
    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 12007078221095272
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 -6674738347.05
    Log(P) -777012.66
    Log S -6.24
    Log(Vapor Pressure) -395387009377461.44
    Melting Point -120139943.47
    pKa Acid -2881019179251.04
    pKa Basic -23177699070.23