Perakine






Names

    • Perakine
    • [formyl(methyl)[?]yl] acetate
    • AKOS032948605
    • [(1R,10S,13R,14S,16S,18R)-13-formyl-14-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6,8-tetraen-18-yl] acetate
    • MS-25413
    • DA-66581
    • 18-Norajmalan-19-al, 17-(acetyloxy)-1,2-didehydro-1-demethyl-21-methyl-, (17R,20a,21b)-
    • Q15425282
    • 4382-56-3
    • HY-N2030
    • Raucaffrine
    • 18-Norajmalan-19-al, 17-(acetyloxy)-1,2-didehydro-1-demethyl-21-methyl-, (17R,20alpha,21beta)-
    • CS-0018521

Attributes

  • Canonical SMILES

    C[C@H]1[C@@H]([C@@H]2C[C@@H]3N1[C@@H]4C2[C@H]([C@@]5(C4)C3=NC6=CC=CC=C56)OC(=O)C)C=O

  • InChI

    InChI=1S/C21H22N2O3/c1-10-13(9-24)12-7-16-19-21(14-5-3-4-6-15(14)22-19)8-17(23(10)16)18(12)20(21)26-11(2)25/h3-6,9-10,12-13,16-18,20H,7-8H2,1-2H3/t10-,12-,13-,16-,17-,18?,20+,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 58.97
  • #RotBonds: 2
  • MW: 350.4180000000001
  • HBD: 0
  • HBA: 5
  • logP: 2.2520000000000007
  • Chemical Formula: C21H22N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. inconspicua Cameroon 761075 NHC61026

External Databases


References

  • A new cytotoxic indole alkaloid from Tabernaemontana inconspicua stapf. Nat Prod Res, 2021 (PMID 31305139).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity

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) -4.86
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.8
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.26
    Distribution Blood-Brain Barrier (Central Nervous System) -2.29
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.52
    Plasma Protein Binding 53.16
    Steady State Volume of Distribution 2.33
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-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 Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 5.07
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -0.57
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.38
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.98
    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 -10.04
    Rat (Acute) 4.36
    Rat (Chronic Oral) 1.06
    Fathead Minnow 4.06
    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 431.36
    Hydration Free Energy -3.09
    Log(D) at pH=7.4 1.45
    Log(P) 1.63
    Log S -3.24
    Log(Vapor Pressure) -8.8
    Melting Point 215.42
    pKa Acid 6.38
    pKa Basic 7.05