Lochnerine






Names

    • HY-N3374
    • ((1S,12S,13R,14R,15E)-15-ethylidene-7-methoxy-3,17-diazapentacyclo(12.3.1.02,10.04,9.012,17)octadeca-2(10),4(9),5,7-tetraen-13-yl)methanol
    • BDBM50480330
    • CS-0024033
    • [(1S,12S,13R,14R,15E)-15-ethylidene-7-methoxy-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4(9),5,7-tetraen-13-yl]methanol
    • Lochnerine
    • AKOS040744703
    • Sarpagan-17-ol, 10-methoxy-
    • CHEMBL484153
    • DTXSID601318507
    • 522-47-4
    • (+)-Lochnerine
    • [(E)-ethylidene(methoxy)[?]yl]methanol

Attributes

  • Canonical SMILES

    C/C=C\1/CN2[C@H]3C[C@@H]1[C@H]([C@@H]2CC4=C3NC5=C4C=C(C=C5)OC)CO

  • InChI

    InChI=1S/C20H24N2O2/c1-3-11-9-22-18-8-15-14-6-12(24-2)4-5-17(14)21-20(15)19(22)7-13(11)16(18)10-23/h3-6,13,16,18-19,21,23H,7-10H2,1-2H3/b11-3-/t13-,16+,18-,19-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 48.49
  • #RotBonds: 2
  • MW: 324.42400000000004
  • HBD: 2
  • HBA: 3
  • logP: 3.032600000000001
  • Chemical Formula: C20H24N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. dichotoma Sri Lanka, Malaysia - -

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Vasorelaxant activity of indole alkaloids from Tabernaemontana dichotoma. J Nat Med, 2013 (PMID 22350216).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Vasorelaxant
    • Inhibitory
    • Xanthine oxidase inhibitory

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) -5.19
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.12
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.39
    Distribution Blood-Brain Barrier (Central Nervous System) -2.89
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.36
    Plasma Protein Binding 58.5
    Steady State Volume of Distribution 3.84
    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 Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.63
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.02
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.0
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.38
    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 -2.76
    Rat (Acute) 2.77
    Rat (Chronic Oral) 2.11
    Fathead Minnow 4.25
    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 441.3
    Hydration Free Energy -4.95
    Log(D) at pH=7.4 2.16
    Log(P) 2.81
    Log S -3.46
    Log(Vapor Pressure) -9.2
    Melting Point 231.55
    pKa Acid 10.42
    pKa Basic 8.44