Bisnaecarpamine A






Names

    • Bisnaecarpamine A

Attributes

  • Canonical SMILES

    C/C=C1[C@H]4CC(C5=CC=C(NC(C7C[C@H]8[C@](CO)9C(OC)=O)=C6C[C@@H]9[N+]7(C)C/C8=C/C)C6=C5)C(NC3=CC=CC=C23)=C2C[C@@H]([C@@H]4C(O)=O)N(C)C/1

  • InChI

    InChI=1S/C42H48N4O5/c1-6-22-19-45(3)34-16-29-25-10-8-9-11-32(25)43-38(29)27(15-26(22)37(34)40(48)49)24-12-13-33-28(14-24)30-17-36-42(21-47,41(50)51-5)31-18-35(39(30)44-33)46(36,4)20-23(31)7-2/h6-14,26-27,31,34-37,43-44,47H,15-21H2,1-5H3/p+1/b22-6+,23-7-/t26-,27?,31-,34+,35?,36+,37-,42-,46?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 118.64999999999999
  • #RotBonds: 4
  • MW: 689.8770000000001
  • HBD: 4
  • HBA: 5
  • logP: 5.848500000000006
  • Chemical Formula: C42H49N4O5+


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. macrocarpa Indonesia 761080 -

External Databases


References

  • Two new bisindole alkaloids from Tabernaemontana macrocarpa Jack. J Nat Med, 2021 (PMID 33822287).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimalarial

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) -5.51
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 5.52
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 1545.07
    Distribution Blood-Brain Barrier (Central Nervous System) -4.37
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.41
    Plasma Protein Binding 101.12
    Steady State Volume of Distribution 1.4
    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 Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 5.76
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Safe
    Bioconcentration Factor -37.16
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.51
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 8.76
    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 -2808067.3
    Rat (Acute) 3.17
    Rat (Chronic Oral) 0.8
    Fathead Minnow 3545.6
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 311934.01
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 2.31
    Log(P) 2.17
    Log S -3.68
    Log(Vapor Pressure) -10229.44
    Melting Point 331.1
    pKa Acid -46.56
    pKa Basic 5.86