19,20-Dihydroervahanine A






Names

    • CHEMBL2018162
    • BDBM50380808
    • 19,20-Dihydroervahanine A

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=CC(=C5)[C@H]6C[C@@H]7[C@@H](CN([C@H](C7C(=O)OC)CC8=C6NC9=CC=CC=C89)C)CC)C(=O)OC

  • InChI

    InChI=1S/C42H52N4O4/c1-6-24-16-23-20-42(41(48)50-5)38-29(14-15-46(21-23)39(24)42)28-13-12-26(17-34(28)44-38)31-18-30-25(7-2)22-45(3)35(36(30)40(47)49-4)19-32-27-10-8-9-11-33(27)43-37(31)32/h8-13,17,23-25,30-31,35-36,39,43-44H,6-7,14-16,18-22H2,1-5H3/t23-,24-,25+,30+,31+,35-,36?,39-,42+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 90.66000000000001
  • #RotBonds: 5
  • MW: 676.9020000000002
  • HBD: 2
  • HBA: 6
  • logP: 6.560200000000007
  • Chemical Formula: C42H52N4O4


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).
  • Vobasinyl-iboga bisindole alkaloids, potent acetylcholinesterase inhibitors from Tabernaemontana divaricata root. J Pharm Pharmacol, 2006 (PMID 16734986).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cholinesterase
    • 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) -5.78
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 3.8
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 1234.61
    Distribution Blood-Brain Barrier (Central Nervous System) -2.72
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.54
    Plasma Protein Binding 92.38
    Steady State Volume of Distribution 4.66
    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 10.97
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -29.04
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.23
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 7.07
    Micronucleos Toxic
    NR-AhR Toxic
    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 -2238672.14
    Rat (Acute) 2.88
    Rat (Chronic Oral) 1.6
    Fathead Minnow 2826.3
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Safe
    General Properties Boiling Point 248348.71
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.9
    Log(P) 6.02
    Log S -5.97
    Log(Vapor Pressure) -8117.54
    Melting Point 315.21
    pKa Acid -27.11
    pKa Basic 6.68