Jerantinine B






Names

    • 10-hydroxy-11-methoxytabersonine alpha-epoxide
    • CHEBI:66120
    • CHEMBL446954
    • DTXSID701317514
    • Q27134638
    • 1067224-91-2
    • methyl (1R,12S,13R,15S,20R)-12-ethyl-4-hydroxy-5-methoxy-14-oxa-8,17-diazahexacyclo[10.7.1.01,9.02,7.013,15.017,20]icosa-2,4,6,9-tetraene-10-carboxylate
    • methyl (5alpha,6alpha,7alpha,12beta,19alpha)-15-hydroxy-16-methoxy-2,3-didehydro-6,7-epoxyaspidospermidine-3-carboxylate
    • Jerantinine B
    • methyl (1R,12S,13R,15S,20R)-12-ethyl-4-hydroxy-5-methoxy-14-oxa-8,17-diazahexacyclo(10.7.1.01,9.02,7.013,15.017,20)icosa-2,4,6,9-tetraene-10-carboxylate

Attributes

  • Canonical SMILES

    CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)C[C@H]5[C@@H]2O5)C6=CC(=C(C=C6N3)OC)O)C(=O)OC

  • InChI

    InChI=1S/C22H26N2O5/c1-4-21-9-11(19(26)28-3)17-22(5-6-24(20(21)22)10-16-18(21)29-16)12-7-14(25)15(27-2)8-13(12)23-17/h7-8,16,18,20,23,25H,4-6,9-10H2,1-3H3/t16-,18-,20-,21+,22-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 83.56000000000002
  • #RotBonds: 3
  • MW: 398.4590000000001
  • HBD: 2
  • HBA: 7
  • logP: 2.1466000000000003
  • 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).
  • Novel antitumour indole alkaloid, Jerantinine A, evokes potent G2/M cell cycle arrest targeting microtubules. Invest New Drugs, 2014 (PMID 24927857).

Compound-Protein Relationships


Compound Activities

    • Proapoptotic
    • Tubulin destabilizing
    • Antiproliferative
    • 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) -5.43
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.12
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.32
    Distribution Blood-Brain Barrier (Central Nervous System) -2.98
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.51
    Plasma Protein Binding 25.48
    Steady State Volume of Distribution 2.76
    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 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 14.22
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.12
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.04
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 8.97
    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 Toxic
    T. Pyriformis -48.42
    Rat (Acute) 2.6
    Rat (Chronic Oral) 2.08
    Fathead Minnow 4.13
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 452.9
    Hydration Free Energy -4.17
    Log(D) at pH=7.4 2.1
    Log(P) 1.23
    Log S -2.88
    Log(Vapor Pressure) -8.81
    Melting Point 199.07
    pKa Acid 5.47
    pKa Basic 6.52