Aspidofractinine






Names

    • 6H,13aH-3a,5a-Ethano-1H-indolizino(8,1-cd)carbazole, 2,3,4,5,11,12-hexahydro-, (10bR-(10bR*,13aS*))-
    • 6H,13aH-3a,5a-Ethano-1H-indolizino[8,1-cd]carbazole, 2,3,4,5,11,12-hexahydro-, [10bR-(10bR*,13aS*)]-
    • Q27116625
    • CHEBI:35918
    • (9R,21S)-2,12-diazahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3,5,7-triene
    • Aspidofractinine

Attributes

  • Canonical SMILES

    C1CC23CCC4(CC2)[C@@]5([C@H]3N(C1)CC5)C6=CC=CC=C6N4

  • InChI

    InChI=1S/C19H24N2/c1-2-5-15-14(4-1)19-11-13-21-12-3-6-17(16(19)21)7-9-18(19,20-15)10-8-17/h1-2,4-5,16,20H,3,6-13H2/t16-,17?,18?,19+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 15.27
  • #RotBonds: 0
  • MW: 280.41499999999996
  • HBD: 1
  • HBA: 2
  • logP: 3.530800000000002
  • Chemical Formula: C19H24N2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862

External Databases


References

  • Chromatographic analysis and antioxidant capacity of Tabernaemontana catharinensis. Nat Prod Commun, 2014 (PMID 24660464).

Compound-Protein Relationships


Compound Activities

    • Antioxidant

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) -4.57
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.95
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.66
    Distribution Blood-Brain Barrier (Central Nervous System) -2.5
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.44
    Plasma Protein Binding 43.07
    Steady State Volume of Distribution 2.68
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-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 Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 15.72
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.24
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.94
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.47
    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 0.52
    Rat (Acute) 3.48
    Rat (Chronic Oral) 1.69
    Fathead Minnow 3.95
    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 388.77
    Hydration Free Energy -3.26
    Log(D) at pH=7.4 2.74
    Log(P) 3.42
    Log S -2.94
    Log(Vapor Pressure) -7.03
    Melting Point 192.29
    pKa Acid 13.81
    pKa Basic 9.14