3-Hydroxy coronaridine






Names

    • 3-Hydroxy coronaridine

Attributes

  • Canonical SMILES

    O=C(OC)[C@]([C@H]1[N@]2CC3)(C[C@@H](C2O)C[C@H]1CC)C4=C3C(C=CC=C5)=C5N4

  • InChI

    InChI=1S/C21H26N2O3/c1-3-12-10-13-11-21(20(25)26-2)17-15(8-9-23(18(12)21)19(13)24)14-6-4-5-7-16(14)22-17/h4-7,12-13,18-19,22,24H,3,8-11H2,1-2H3/t12-,13+,18+,19?,21-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 65.56
  • #RotBonds: 2
  • MW: 354.45000000000005
  • HBD: 2
  • HBA: 4
  • logP: 2.5736
  • Chemical Formula: C21H26N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata. Molecules, 2023 (PMID 37764440).

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) -4.94
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.91
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.62
    Distribution Blood-Brain Barrier (Central Nervous System) -3.17
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.87
    Plasma Protein Binding 61.09
    Steady State Volume of Distribution 4.63
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-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 8.75
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.06
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.59
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.13
    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 -10.55
    Rat (Acute) 3.3
    Rat (Chronic Oral) 2.13
    Fathead Minnow 4.11
    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 422.43
    Hydration Free Energy -6.6
    Log(D) at pH=7.4 2.61
    Log(P) 2.6
    Log S -3.14
    Log(Vapor Pressure) -8.92
    Melting Point 217.28
    pKa Acid 8.92
    pKa Basic 7.13