19,20-Dihydrovobparicine






Names

    • 19,20-Dihydrovobparicine

Attributes

  • Canonical SMILES

    [H][C@@]12C[C@H](CC)[C@@]3([H])C(C1)C1=C(CCN3C2)C2=CC(=CC=C2N1)[C@H]1C[C@]2([H])[C@H](CC)CN(C)[C@@]([H])(CC3=C1NC1=CC=CC=C31)[C@H]2C(=O)OC

  • InChI

    InChI=1S/C40H50N4O2/c1-5-23-15-22-16-32-37-27(13-14-44(20-22)39(23)32)30-17-25(11-12-34(30)42-37)29-18-28-24(6-2)21-43(3)35(36(28)40(45)46-4)19-31-26-9-7-8-10-33(26)41-38(29)31/h7-12,17,22-24,28-29,32,35-36,39,41-42H,5-6,13-16,18-21H2,1-4H3/t22-,23+,24-,28-,29-,32?,35+,36+,39+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 64.36
  • #RotBonds: 4
  • MW: 618.8660000000003
  • HBD: 2
  • HBA: 4
  • logP: 7.233000000000008
  • Chemical Formula: C40H50N4O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata. J Nat Prod, 2018 (PMID 30169038).
  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antiinflammatory
    • Cytotoxicity
    • Acetylcholinesterase inhibitory
    • Antiproliferative

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) -5.9
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -3.96
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 214.05
    Distribution Blood-Brain Barrier (Central Nervous System) -3.45
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.55
    Plasma Protein Binding 100.87
    Steady State Volume of Distribution 5.24
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate 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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.59
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.64
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.12
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.41
    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 -386376.29
    Rat (Acute) 2.82
    Rat (Chronic Oral) 2.11
    Fathead Minnow 492.57
    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 39872.87
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.95
    Log(P) 6.15
    Log S -5.93
    Log(Vapor Pressure) -1293.07
    Melting Point 295.85
    pKa Acid 6.41
    pKa Basic 6.89