Jerantinine F






Names

    • methyl (5alpha,6alpha,12beta,19alpha)-15-hydroxy-16-methoxy-2,3-didehydro-6,21-epoxyaspidospermidine-3-carboxylate
    • CHEMBL524840
    • methyl (1R,12R,16S,22R)-4-hydroxy-5-methoxy-15-oxa-8,19-diazahexacyclo(10.9.1.01,9.02,7.012,16.019,22)docosa-2,4,6,9-tetraene-10-carboxylate
    • DTXSID501317520
    • 1067224-95-6
    • Q27134645
    • CHEBI:66124
    • methyl (1R,12R,16S,22R)-4-hydroxy-5-methoxy-15-oxa-8,19-diazahexacyclo[10.9.1.01,9.02,7.012,16.019,22]docosa-2,4,6,9-tetraene-10-carboxylate
    • Jerantinine F

Attributes

  • Canonical SMILES

    COC1=C(O)C=C2C(NC3=C(C(OC)=O)C[C@]45CCO[C@H]4CCN6[C@]5([H])[C@@]23CC6)=C1

  • InChI

    InChI=1S/C22H26N2O5/c1-27-16-10-14-13(9-15(16)25)22-4-7-24-6-3-17-21(20(22)24,5-8-29-17)11-12(18(22)23-14)19(26)28-2/h9-10,17,20,23,25H,3-8,11H2,1-2H3/t17-,20-,21+,22-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 80.25999999999999
  • #RotBonds: 2
  • MW: 398.4590000000002
  • HBD: 2
  • HBA: 7
  • logP: 2.1482
  • Chemical Formula: C22H26N2O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Jerantinines A-G, cytotoxic Aspidosperma alkaloids from Tabernaemontana corymbosa. J Nat Prod, 2008 (PMID 18778099).

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) -5.5
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.28
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.1
    Distribution Blood-Brain Barrier (Central Nervous System) -2.93
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.62
    Plasma Protein Binding 38.51
    Steady State Volume of Distribution 4.93
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate 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 10.17
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.02
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.12
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 9.64
    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 -55.11
    Rat (Acute) 2.63
    Rat (Chronic Oral) 2.3
    Fathead Minnow 4.12
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 445.05
    Hydration Free Energy -3.85
    Log(D) at pH=7.4 2.26
    Log(P) 1.29
    Log S -2.87
    Log(Vapor Pressure) -8.94
    Melting Point 230.4
    pKa Acid 6.93
    pKa Basic 6.82