Ervadivaricatine B






Names

    • Ervadivaricatine B
    • 204581-20-4
    • Methyl 12-methoxy-13-(17-methoxy-17-oxo-19,20-dihydrovobasan-3-yl)ibogamine-18-carboxylate
    • DTXSID40942632

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=CC(=C(C=C45)OC)[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/C43H54N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h9-12,17,19,23-25,28,31,35,37,40,44-45H,7-8,13-16,18,20-22H2,1-6H3/t23-,24+,25-,28-,31+,35-,37?,40+,43-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 99.89
  • #RotBonds: 6
  • MW: 706.9280000000001
  • HBD: 2
  • HBA: 7
  • logP: 6.5688000000000075
  • Chemical Formula: C43H54N4O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. officinalis China - Cai20120227

External Databases

    • PubChem CID: 183141
    • CAS RN: 204581-20-4

References

  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Iboga-type alkaloids with Indolizidino[8,7-b]Indole scaffold and bisindole alkaloids from Tabernaemontana bufalina Lour. Phytochemistry, 2022 (PMID 35074605).
  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).
  • Two new monoterpenoid indole alkaloids from Tabernaemontana divaricata. Nat Prod Res, 2019 (PMID 30445827).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antiinflammatory
    • α-glucosidase inhibitory
    • Antimicrobial
    • Cytotoxicity
    • Acetylcholinesterase inhibitory
    • Butyrylcholinesterase

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) -5.73
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 17.48
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 3029.34
    Distribution Blood-Brain Barrier (Central Nervous System) -2.55
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.32
    Plasma Protein Binding 86.39
    Steady State Volume of Distribution 4.45
    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 Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 10.43
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -73.65
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.34
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 6.69
    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 -5495963.97
    Rat (Acute) 2.8
    Rat (Chronic Oral) 1.63
    Fathead Minnow 6938.48
    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 614605.83
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 6.08
    Log(P) 5.83
    Log S -5.84
    Log(Vapor Pressure) -20169.09
    Melting Point 312.89
    pKa Acid -109.36
    pKa Basic 6.66