Contortamide






Names

    • Contortamide

Attributes

  • Canonical SMILES

    O[C@H]1[C@@H](O)[C@@H](O)[C@H](OC[C@H](NC([C@@H](O)CCCCCCCCCCCCCCCCCCCCCCCCC)=O)[C@H](O)[C@H](O)C/C=C/CCCCCCCCCCCCCCCCCCC)OC1CO

  • InChI

    InChI=1S/C59H115NO10/c1-3-5-7-9-11-13-15-17-19-21-23-25-26-27-29-31-33-35-37-39-41-43-45-47-52(63)58(68)60-50(49-69-59-57(67)56(66)55(65)53(48-61)70-59)54(64)51(62)46-44-42-40-38-36-34-32-30-28-24-22-20-18-16-14-12-10-8-6-4-2/h42,44,50-57,59,61-67H,3-41,43,45-49H2,1-2H3,(H,60,68)/b44-42+/t50-,51+,52-,53?,54-,55+,56+,57+,59+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 189.16999999999996
  • #RotBonds: 52
  • MW: 998.5659999999995
  • HBD: 8
  • HBA: 10
  • logP: 12.740699999999983
  • Chemical Formula: C59H115NO10


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. contorta Cameroon 761060 N43440/HNC

External Databases


References

  • Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae). Nat Prod Res, 2021 (PMID 31274013).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticolon cancer

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) -5.55
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 15546.16
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 2032478.8
    Distribution Blood-Brain Barrier (Central Nervous System) -2.32
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 1.74
    Plasma Protein Binding 92.72
    Steady State Volume of Distribution 0.22
    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 Non-Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance -0.79
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life >= 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Safe
    Bioconcentration Factor -47264.96
    Biodegradation Toxic
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.34
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 4.05
    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 -3688855167.64
    Rat (Acute) 2.52
    Rat (Chronic Oral) 11.28
    Fathead Minnow 4656406.29
    Respiratory Disease Safe
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 414890890.93
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 -198.0
    Log(P) 19.65
    Log S -7.15
    Log(Vapor Pressure) -13661990.57
    Melting Point 77.55
    pKa Acid -99463.16
    pKa Basic -784.77