Pachysiphine






Names

    • Lochnericin
    • Aspidospermidine-3-carboxylic acid,3-didehydro-6,7-epoxy-, methyl ester, (5.alpha.,6.beta.,7.beta.,12.beta.,19.alpha.)-
    • (5alpha,12R,19alpha)-2,3-Didehydro-6alpha,7alpha-epoxyaspidospermidine-3-carboxylic acid methyl ester
    • (-)-Pachysiphine
    • NSC251683
    • Methyl 12-ethyl-14-oxa-8,17-diazahexacyclo[10.7.1.01,9.02,7.013,15.017,20]icosa-2,4,6,9-tetraene-10-carboxylate
    • Pachysiphine
    • NSC-251683
    • DTXSID80312234
    • 2447-58-7

Attributes

  • Canonical SMILES

    CC[C@@]12[C@H](O3)[C@H]3CN(CC4)[C@]1([H])C54C6=CC=C(OC)C=C6NC5=C(C(OC)=O)C2

  • InChI

    InChI=1S/C22H26N2O4/c1-4-21-10-13(19(25)27-3)17-22(14-6-5-12(26-2)9-15(14)23-17)7-8-24(20(21)22)11-16-18(21)28-16/h5-6,9,16,18,20,23H,4,7-8,10-11H2,1-3H3/t16-,18-,20+,21-,22?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 63.330000000000005
  • #RotBonds: 3
  • MW: 382.46000000000015
  • HBD: 1
  • HBA: 6
  • logP: 2.441
  • Chemical Formula: C22H26N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).

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) -5.21
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.95
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.72
    Distribution Blood-Brain Barrier (Central Nervous System) -2.75
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.48
    Plasma Protein Binding 23.56
    Steady State Volume of Distribution 2.71
    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 Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 12.69
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.51
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.0
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 8.57
    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 Toxic
    T. Pyriformis -32.2
    Rat (Acute) 2.91
    Rat (Chronic Oral) 1.91
    Fathead Minnow 4.08
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 443.0
    Hydration Free Energy -4.34
    Log(D) at pH=7.4 2.75
    Log(P) 2.45
    Log S -2.71
    Log(Vapor Pressure) -7.96
    Melting Point 167.39
    pKa Acid 5.83
    pKa Basic 6.68