Pachysipine






Names

    • 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
    • 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
    • Pachysipine
    • 2447-58-7
    • Pachysiphine
    • DTXSID80312234
    • NSC251683
    • NSC-251683
    • Lochnericin

Attributes

  • Canonical SMILES

    CC[C@]34CC(C(OC)=O)=C([C@]62C3N(CC6)C[C@@H]5[C@H]4O5)NC1=C2C=CC=C1

  • InChI

    InChI=1S/C21H24N2O3/c1-3-20-10-12(18(24)25-2)16-21(13-6-4-5-7-14(13)22-16)8-9-23(19(20)21)11-15-17(20)26-15/h4-7,15,17,19,22H,3,8-11H2,1-2H3/t15-,17-,19?,20-,21+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 54.1
  • #RotBonds: 2
  • MW: 352.434
  • HBD: 1
  • HBA: 5
  • logP: 2.4324000000000003
  • Chemical Formula: C21H24N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -5.06
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.9
    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) -2.59
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.46
    Plasma Protein Binding 24.45
    Steady State Volume of Distribution 2.66
    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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.99
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.41
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.09
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 7.51
    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 -13.98
    Rat (Acute) 3.08
    Rat (Chronic Oral) 1.88
    Fathead Minnow 4.07
    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 420.8
    Hydration Free Energy -5.98
    Log(D) at pH=7.4 2.5
    Log(P) 2.3
    Log S -2.71
    Log(Vapor Pressure) -7.55
    Melting Point 158.1
    pKa Acid 5.71
    pKa Basic 6.75