Eleganine A






Names

    • Eleganine A

Attributes

  • Canonical SMILES

    C/C=C1CN2[C@](CC3=C(NC4=C3C=CC=C4)C(C[C@@]/1([H])[C@]2([H])C(OC)=O)=O)([H])OC

  • InChI

    InChI=1S/C21H24N2O4/c1-4-12-11-23-18(26-2)10-15-13-7-5-6-8-16(13)22-19(15)17(24)9-14(12)20(23)21(25)27-3/h4-8,14,18,20,22H,9-11H2,1-3H3/b12-4-/t14-,18-,20-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 71.63
  • #RotBonds: 2
  • MW: 368.43300000000016
  • HBD: 1
  • HBA: 5
  • logP: 2.689000000000001
  • Chemical Formula: C21H24N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM

External Databases


References

  • Induction of apoptosis in HuH-7 cancer cells by monoterpene and beta-carboline indole alkaloids isolated from the leaves of Tabernaemontana elegans. Bioorg Med Chem Lett, 2009 (PMID 19525111).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Apoptosis

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) -4.84
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.77
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.98
    Distribution Blood-Brain Barrier (Central Nervous System) -2.5
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.85
    Plasma Protein Binding 47.21
    Steady State Volume of Distribution 3.99
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 13.02
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.03
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.92
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.36
    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 -11.63
    Rat (Acute) 2.94
    Rat (Chronic Oral) 1.98
    Fathead Minnow 4.44
    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 438.76
    Hydration Free Energy -6.19
    Log(D) at pH=7.4 2.4
    Log(P) 2.23
    Log S -3.65
    Log(Vapor Pressure) -8.49
    Melting Point 194.21
    pKa Acid 8.79
    pKa Basic 5.15