Isositsirikine






Names

    • Corynan-16-carboxylic acid, 19,20-didehydro-17-hydroxy-, methyl ester, (16R,19E)-
    • CS-0016094
    • SCHEMBL23675913
    • FS-8676
    • NSC 282700
    • DTXSID401317258
    • 16-epi-Isositsirikine
    • CHEMBL3940308
    • 16R,19E-isositsirikine
    • (16R)-E-Isositsirikine
    • HY-N0959
    • AKOS032948969
    • Q27138840
    • (16R,19E)-isositsirikine
    • methyl (2R)-2-[(2R,3E,12bS)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoate
    • 6519-27-3
    • 17,18-Secoyohimban-16-carboxylic acid, 19,20-didehydro-17-hydroxy-, methyl ester, (16S,19E)-
    • Isositsirikine
    • NSC 338932
    • CHEBI:70508

Attributes

  • Canonical SMILES

    C/C=C\1/CN2CCC3=C([C@@H]2C[C@@H]1[C@H](CO)C(=O)OC)NC4=CC=CC=C34

  • InChI

    InChI=1S/C21H26N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,16-17,19,22,24H,8-12H2,1-2H3/b13-3-/t16-,17-,19-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 65.56
  • #RotBonds: 3
  • MW: 354.45000000000005
  • HBD: 2
  • HBA: 4
  • logP: 2.814800000000001
  • Chemical Formula: C21H26N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. chippii Ivory Coast - Lg12291
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM
    T. macrocarpa Indonesia 761080 -

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Characterization of a Suspension Culture of Tabernaemontana elegans on Growth, Nutrient Uptake, and Accumulation of Indole Alkaloids*. Planta Med, 1989 (PMID 17262332).
  • Two new sarpagine-type indole alkaloids and antimalarial activity of 16-demethoxycarbonylvoacamine from Tabernaemontana macrocarpa Jack. J Nat Med, 2019 (PMID 31140017).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimalarial
    • Xanthine oxidase inhibitory
    • Inhibitory
    • Antimicrobial
    • 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) -5.16
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.03
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.99
    Distribution Blood-Brain Barrier (Central Nervous System) -2.56
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.83
    Plasma Protein Binding 57.94
    Steady State Volume of Distribution 5.27
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.81
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Safe
    Bioconcentration Factor 0.33
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.87
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.53
    Micronucleos Toxic
    NR-AhR Toxic
    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 -7.01
    Rat (Acute) 2.96
    Rat (Chronic Oral) 2.33
    Fathead Minnow 4.45
    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 438.55
    Hydration Free Energy -7.22
    Log(D) at pH=7.4 2.52
    Log(P) 2.61
    Log S -3.24
    Log(Vapor Pressure) -9.34
    Melting Point 180.92
    pKa Acid 10.31
    pKa Basic 6.63