Aspidospermidine






Names

    • 2912-09-6
    • (+)-Aspidospermidine
    • YAAIPCQYJYPITK-UHFFFAOYSA-N
    • Q15410259
    • [3aR-(3a.alpha.,5a.beta.,10bR*,13a.alpha.)]-3a-Ethyl-2,3,3a,4,5,5a,6, 11,12,13a-decahydro-1H-indolizino[8,1-cd]carbazole
    • 1H-Indolizino[8,1-cd]carbazole, 3a-ethyl-2,3,3a,4,5,5a,6,11,12,13a-decahydro-, [3aR-(3a.alpha.,5a.beta.,10bR*,13a.alpha.)]-
    • Aspidospermidine
    • CHEBI:174012
    • 12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6-triene
    • 1H-Indolizino[8,1-cd]carbazole, 3a-ethyl-2,3,3a,4,5,5a,6,11,12,13a-decahydro-, [3aR-(3a.alpha.,5a.beta.,10bR,13a.alpha.)]-

Attributes

  • Canonical SMILES

    CC[C@]12CCCN3[C@@]1([H])[C@]4([C@@](NC5=CC=CC=C45)([H])CC2)CC3

  • InChI

    InChI=1S/C19H26N2/c1-2-18-9-5-12-21-13-11-19(17(18)21)14-6-3-4-7-15(14)20-16(19)8-10-18/h3-4,6-7,16-17,20H,2,5,8-13H2,1H3/t16-,17-,18-,19-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 15.27
  • #RotBonds: 1
  • MW: 282.4310000000001
  • HBD: 1
  • HBA: 2
  • logP: 3.7768000000000024
  • Chemical Formula: C19H26N2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Inhibitory
    • Cytotoxicity
    • 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) -4.74
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.09
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -3.07
    Distribution Blood-Brain Barrier (Central Nervous System) -2.49
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.67
    Plasma Protein Binding 57.35
    Steady State Volume of Distribution 3.11
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-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 15.82
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor 0.98
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.85
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.07
    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 1.2
    Rat (Acute) 3.31
    Rat (Chronic Oral) 1.66
    Fathead Minnow 3.92
    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 382.31
    Hydration Free Energy -4.85
    Log(D) at pH=7.4 2.91
    Log(P) 3.78
    Log S -2.83
    Log(Vapor Pressure) -6.51
    Melting Point 154.92
    pKa Acid 13.32
    pKa Basic 8.81