19,20-Dihydrotabernamine






Names

    • BDBM50380807
    • 19,20-dihydrotabernamine
    • CHEMBL376478
    • methyl (1R,12S,14R,15S)-15-ethyl-12-[(1R,15R,17S,18S)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraen-6-yl]-17-methyl-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate
    • methyl (1R,12S,14R,15S)-15-ethyl-12-((1R,15R,17S,18S)-17-ethyl-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraen-6-yl)-17-methyl-10,17-diazatetracyclo(12.3.1.03,11.04,9)octadeca-3(11),4,6,8-tetraene-18-carboxylate
    • 19,20-Dihydrotabernamine

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@@H]2C[C@@H]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

  • InChI

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

  • Molecule Class: Alkaloids
  • TPSA: 64.36000000000001
  • #RotBonds: 4
  • MW: 618.8660000000002
  • HBD: 2
  • HBA: 4
  • logP: 7.2330000000000085
  • 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).
  • 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).
  • 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

    • Antiproliferative
    • Cholinesterase
    • Antiinflammatory
    • α-glucosidase inhibitory
    • Antimicrobial
    • Acetylcholinesterase inhibitory
    • Cytotoxicity
    • 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) -5.82
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -3.94
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 214.31
    Distribution Blood-Brain Barrier (Central Nervous System) -3.11
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.68
    Plasma Protein Binding 102.34
    Steady State Volume of Distribution 3.92
    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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 8.05
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.54
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.46
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 7.16
    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 Toxic
    T. Pyriformis -385625.47
    Rat (Acute) 3.09
    Rat (Chronic Oral) 1.1
    Fathead Minnow 489.02
    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 39467.1
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.8
    Log(P) 6.26
    Log S -6.2
    Log(Vapor Pressure) -1278.84
    Melting Point 300.24
    pKa Acid 7.39
    pKa Basic 7.26