Bistabercarpamine B






Names

    • Bistabercarpamine B

Attributes

  • Canonical SMILES

    C/C=C1[C@@]2([H])C[C@H](C3=CC(C4=C5N6C[C@@](CC[C@H]7CC)([H])C[C@]5(C(OC)=O)[C@]7([H])NCC4)=C6C=C3OC)C8=C(C[C@]([C@@]2([H])C(OC)=O)([H])N(C)C\1)C9=C(N8)C=CC=C9

  • InChI

    InChI=1S/C44H54N4O5/c1-7-25-14-13-24-21-44(43(50)53-6)40(25)45-16-15-28-30-18-31(37(51-4)20-35(30)48(22-24)41(28)44)32-17-29-26(8-2)23-47(3)36(38(29)42(49)52-5)19-33-27-11-9-10-12-34(27)46-39(32)33/h8-12,18,20,24-25,29,32,36,38,40,45-46H,7,13-17,19,21-23H2,1-6H3/b26-8-/t24-,25-,29-,32-,36+,38+,40-,44+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 97.82
  • #RotBonds: 5
  • MW: 718.9390000000002
  • HBD: 2
  • HBA: 8
  • logP: 6.640000000000007
  • Chemical Formula: C44H54N4O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbose Malaysia - K667

External Databases


References

  • Bistabercarpamines A and B, first vobasinyl-chippiine-type bisindole alkaloid from Tabernaemontana corymbosa Tetrahedron Letters, 2014 (DOI).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Growth 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) -5.71
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 27.31
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 4297.68
    Distribution Blood-Brain Barrier (Central Nervous System) -2.92
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.46
    Plasma Protein Binding 81.83
    Steady State Volume of Distribution 4.25
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 12.51
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -104.7
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.63
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.29
    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 -7801244.46
    Rat (Acute) 2.97
    Rat (Chronic Oral) 2.09
    Fathead Minnow 9851.56
    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 874092.68
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.63
    Log(P) 5.6
    Log S -5.22
    Log(Vapor Pressure) -28713.06
    Melting Point 258.61
    pKa Acid -165.63
    pKa Basic 6.55