Bistabercarpamine A






Names

    • Bistabercarpamine A

Attributes

  • Canonical SMILES

    C/C=C1[C@@]2([H])C[C@H](C3=C(OC)C=CC4=C3N5C6=C4CCN[C@@]7([H])[C@]6(C[C@](CC[C@H]7CC)([H])C5)C(OC)=O)C8=C(C[C@]([C@@]2(CO)C(OC)=O)([H])N(C)C\1)C9=C(N8)C=CC=C9

  • InChI

    InChI=1S/C45H56N4O6/c1-7-26-14-13-25-21-44(42(51)54-5)40(26)46-18-17-30-29-15-16-35(53-4)37(39(29)49(22-25)41(30)44)32-19-33-27(8-2)23-48(3)36(45(33,24-50)43(52)55-6)20-31-28-11-9-10-12-34(28)47-38(31)32/h8-12,15-16,25-26,32-33,36,40,46-47,50H,7,13-14,17-24H2,1-6H3/b27-8-/t25-,26-,32-,33-,36+,40-,44+,45+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 118.05000000000001
  • #RotBonds: 6
  • MW: 748.9650000000001
  • HBD: 3
  • HBA: 9
  • logP: 6.0025000000000075
  • Chemical Formula: C45H56N4O6


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) -5.85
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 76.01
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 10682.76
    Distribution Blood-Brain Barrier (Central Nervous System) -3.22
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.15
    Plasma Protein Binding 80.08
    Steady State Volume of Distribution 3.6
    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 11.45
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -252.91
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.7
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.05
    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 Toxic
    T. Pyriformis -19388933.35
    Rat (Acute) 2.94
    Rat (Chronic Oral) 2.42
    Fathead Minnow 24478.35
    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 2177137.86
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.16
    Log(P) 4.94
    Log S -5.15
    Log(Vapor Pressure) -71610.67
    Melting Point 248.65
    pKa Acid -469.14
    pKa Basic 6.29