Ervachinine B






Names

    • Ervachinine B

Attributes

  • Canonical SMILES

    C/C=C1[C@]2([H])C[C@@](C3=C(OC)C=C4C(C(CCN(C5)[C@]6([H])[C@@]7(C(OC)=O)C[C@]5([H])C[C@@H]6CC)=C7[N]4)=C3)([H])C8=C(C[C@@]([C@@]2(CO)C(OC)=O)([H])N(C)C\1)C9=C(N8)C=CC=C9

  • InChI

    InChI=1S/C44H53N4O6/c1-7-25-15-24-20-43(41(50)53-5)39-28(13-14-48(21-24)40(25)43)29-16-30(36(52-4)19-35(29)46-39)31-17-33-26(8-2)22-47(3)37(44(33,23-49)42(51)54-6)18-32-27-11-9-10-12-34(27)45-38(31)32/h8-12,16,19,24-25,31,33,37,40,45,49H,7,13-15,17-18,20-23H2,1-6H3/b26-8-/t24-,25-,31+,33-,37+,40-,43+,44-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 118.43
  • #RotBonds: 6
  • MW: 733.9300000000002
  • HBD: 2
  • HBA: 8
  • logP: 5.926900000000008
  • Chemical Formula: C44H53N4O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity

Predicted NMR Spectral Data

  • No NMR data available.

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) -6.05
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 50.78
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 7385.71
    Distribution Blood-Brain Barrier (Central Nervous System) -3.18
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.19
    Plasma Protein Binding 80.67
    Steady State Volume of Distribution 4.34
    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 Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 6.99
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -176.9
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.2
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.34
    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 -13404605.12
    Rat (Acute) 2.87
    Rat (Chronic Oral) 2.01
    Fathead Minnow 16923.59
    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 1504191.82
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.91
    Log(P) 4.52
    Log S -5.1
    Log(Vapor Pressure) -49449.14
    Melting Point 233.18
    pKa Acid -311.38
    pKa Basic 5.39