Hecubine






Names

    • (15S,16S,18R)-15-ethyl-11-methyl-17-oxa-1,11-diazapentacyclo(13.4.1.04,12.05,10.016,18)icosa-4(12),5,7,9-tetraene
    • AKOS040761819
    • (15S,16S,18R)-15-ethyl-11-methyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraene
    • Hecubine
    • 62874-52-6

Attributes

  • Canonical SMILES

    CC[C@]12CCC3=C(CCN(C1)C[C@@H]4[C@H]2O4)C5=CC=CC=C5N3C

  • InChI

    InChI=1S/C20H26N2O/c1-3-20-10-8-17-15(14-6-4-5-7-16(14)21(17)2)9-11-22(13-20)12-18-19(20)23-18/h4-7,18-19H,3,8-13H2,1-2H3/t18-,19-,20+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 20.7
  • #RotBonds: 1
  • MW: 310.44100000000003
  • HBD: 0
  • HBA: 3
  • logP: 3.1464000000000016
  • Chemical Formula: C20H26N2O


Species

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

External Databases


References

  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).
  • New Iboga-Type Indole Alkaloids from Tabernaemontana divaricata. Nat Prod Bioprospect, 2019 (PMID 31724098).
  • Virtual Screening of compounds from Tabernaemontana divaricata for potential anti-bacterial activity. Bioinformation, 2014 (PMID 24748755).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antibacterial
    • 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) -4.97
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.65
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.91
    Distribution Blood-Brain Barrier (Central Nervous System) -2.93
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.42
    Plasma Protein Binding 32.15
    Steady State Volume of Distribution 1.81
    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 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 Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 13.3
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.5
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.62
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.97
    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 -1.66
    Rat (Acute) 2.67
    Rat (Chronic Oral) 1.04
    Fathead Minnow 4.07
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 418.78
    Hydration Free Energy -5.44
    Log(D) at pH=7.4 3.0
    Log(P) 3.42
    Log S -2.36
    Log(Vapor Pressure) -7.15
    Melting Point 139.31
    pKa Acid 9.32
    pKa Basic 6.93