Tabercrassine A






Names

    • Tabercrassine A

Attributes

  • Canonical SMILES

    O=C([C@]12C3=C(C4=CC(OC)=CC=C4N3)CC[N@]([C@H]1[C@H](C[C@@]5(C2)[H])CC)[C@@H]5CC(C[C@@H]6[N@]7[C@@H]8[C@](C[C@@]6(C[C@H]8CC)[H])(C9=NC%10=CC=C(C=C%10[C@@]9(CC7)O)OC)C(OC)=O)=O)OC

  • InChI

    InChI=1S/C47H58N4O8/c1-7-25-17-27-23-45(43(53)58-5)39-32(33-21-30(56-3)9-11-35(33)48-39)13-15-50(40(25)45)37(27)19-29(52)20-38-28-18-26(8-2)41-46(24-28,44(54)59-6)42-47(55,14-16-51(38)41)34-22-31(57-4)10-12-36(34)49-42/h9-12,21-22,25-28,37-38,40-41,48,55H,7-8,13-20,23-24H2,1-6H3/t25-,26+,27+,28-,37+,38-,40-,41-,45+,46+,47+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 142.99
  • #RotBonds: 10
  • MW: 807.0010000000002
  • HBD: 2
  • HBA: 11
  • logP: 6.016300000000007
  • Chemical Formula: C47H58N4O8


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. crassa Ghana 761062 20161116

External Databases


References

  • New Monoterpenoid Indole Alkaloids from Tabernaemontana crassa Inhibit β-Amyloid42 Production and Phospho-Tau (Thr217). Int J Mol Sci, 2023 (PMID 36675001).

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) -5.74
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 660.42
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 87073.48
    Distribution Blood-Brain Barrier (Central Nervous System) -2.6
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 1.02
    Plasma Protein Binding 87.97
    Steady State Volume of Distribution 2.88
    Metabolism Breast Cancer Resistance Protein Non-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 Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 2.73
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -2027.18
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.32
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.25
    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 -158032116.07
    Rat (Acute) 2.91
    Rat (Chronic Oral) 1.67
    Fathead Minnow 199484.16
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 17769966.64
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 3.54
    Log(P) 4.91
    Log S -4.97
    Log(Vapor Pressure) -585072.35
    Melting Point 320.03
    pKa Acid -4199.68
    pKa Basic 1.16