Akuammiline






Names

    • Methyl (1S,10S,12R,13E)-18-(acetyloxymethyl)-13-ethylidene-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2,4,6,8-tetraene-18-carboxylate
    • 1897-26-3
    • Akuammiline
    • DA-50298
    • FS-9433

Attributes

  • Canonical SMILES

    C/C=C1[C@@]2([H])C[C@@H]3C4=NC5=CC=CC=C5C4(C2(C(OC)=O)COC(C)=O)CCN3C/1

  • InChI

    InChI=1S/C23H26N2O4/c1-4-15-12-25-10-9-22-16-7-5-6-8-18(16)24-20(22)19(25)11-17(15)23(22,21(27)28-3)13-29-14(2)26/h4-8,17,19H,9-13H2,1-3H3/b15-4+/t17-,19-,22?,23?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 68.2
  • #RotBonds: 3
  • MW: 394.4710000000003
  • HBD: 0
  • HBA: 6
  • logP: 2.7871000000000006
  • Chemical Formula: C23H26N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. chippii Ivory Coast - Lg12291

External Databases


References

  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimicrobial

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) -4.84
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.83
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.54
    Distribution Blood-Brain Barrier (Central Nervous System) -1.95
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.16
    Plasma Protein Binding 65.19
    Steady State Volume of Distribution 2.42
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-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 Non-Inhibitor
    Excretion Clearance 5.44
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.03
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.06
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.13
    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 -33.15
    Rat (Acute) 3.53
    Rat (Chronic Oral) 2.01
    Fathead Minnow 4.63
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 429.56
    Hydration Free Energy -3.82
    Log(D) at pH=7.4 2.33
    Log(P) 2.39
    Log S -3.23
    Log(Vapor Pressure) -7.5
    Melting Point 156.17
    pKa Acid 7.69
    pKa Basic 6.39