3′-(2-Oxopropyl)ervahanine B






Names

    • 3′-(2-Oxopropyl)ervahanine B

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@H]2C[C@@]3([C@H]1N(CCC1=C3NC3=C1C=C(C=C3)[C@H]1C[C@H]3C([C@@H](CC4=C1NC1=CC=CC=C41)N(C)C\C3=C/C)C(=O)OC)C2CC(C)=O)C(=O)OC

  • InChI

    InChI=1S/C45H54N4O5/c1-7-25-18-28-22-45(44(52)54-6)41-30(15-16-49(42(25)45)37(28)17-24(3)50)33-19-27(13-14-36(33)47-41)32-20-31-26(8-2)23-48(4)38(39(31)43(51)53-5)21-34-29-11-9-10-12-35(29)46-40(32)34/h8-14,19,25,28,31-32,37-39,42,46-47H,7,15-18,20-23H2,1-6H3/b26-8+/t25-,28-,31+,32+,37?,38+,39?,42-,45+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 107.73
  • #RotBonds: 6
  • MW: 730.95
  • HBD: 2
  • HBA: 7
  • logP: 6.828000000000007
  • Chemical Formula: C45H54N4O5


Species

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

External Databases


References

  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity
    • Antiinflammatory
    • Acetylcholinesterase 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) -5.84
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 46.18
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 6798.9
    Distribution Blood-Brain Barrier (Central Nervous System) -3.66
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.4
    Plasma Protein Binding 92.27
    Steady State Volume of Distribution 4.65
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate 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 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 12.49
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -163.13
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.36
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.14
    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 -12337377.51
    Rat (Acute) 2.93
    Rat (Chronic Oral) 2.22
    Fathead Minnow 15575.44
    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 1384097.86
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.35
    Log(P) 5.37
    Log S -5.72
    Log(Vapor Pressure) -45508.73
    Melting Point 265.61
    pKa Acid -281.59
    pKa Basic 4.54