(7S)-Geissoschizoloxindole






Names

    • (7S)-Geissoschizoloxindole

Attributes

  • Canonical SMILES

    O=C(C12[C@@]3([H])C[C@](/C(CN3CC2)=C\C)(CCO)[H])NC4=C1C=CC=C4

  • InChI

    InChI=1S/C19H24N2O2/c1-2-13-12-21-9-8-19(17(21)11-14(13)7-10-22)15-5-3-4-6-16(15)20-18(19)23/h2-6,14,17,22H,7-12H2,1H3,(H,20,23)/b13-2-/t14-,17-,19?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 52.57000000000001
  • #RotBonds: 2
  • MW: 312.413
  • HBD: 2
  • HBA: 3
  • logP: 2.2994000000000003
  • Chemical Formula: C19H24N2O2


Species

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

External Databases


References

  • Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine. J Nat Prod, 2014 (PMID 25333996).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -4.87
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.88
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.64
    Distribution Blood-Brain Barrier (Central Nervous System) -2.48
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.53
    Plasma Protein Binding 54.07
    Steady State Volume of Distribution 3.79
    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 Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.02
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.62
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.9
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.11
    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 -1.96
    Rat (Acute) 3.1
    Rat (Chronic Oral) 2.16
    Fathead Minnow 4.21
    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 415.4
    Hydration Free Energy -7.04
    Log(D) at pH=7.4 1.27
    Log(P) 1.46
    Log S -2.45
    Log(Vapor Pressure) -8.58
    Melting Point 166.21
    pKa Acid 8.82
    pKa Basic 6.87