5R-(2-Oxopropyl)coronaridine






Names

    • 5R-(2-Oxopropyl)coronaridine

Attributes

  • Canonical SMILES

    O=[C@@](OC)[C@]34C2=C(C[C@@H](CC(C)=O)N(C5)C3[C@@H](CC)C[C@H]5C4)C1=CC=CC=C1N2

  • InChI

    InChI=1S/C24H30N2O3/c1-4-16-10-15-12-24(23(28)29-3)21-19(18-7-5-6-8-20(18)25-21)11-17(9-14(2)27)26(13-15)22(16)24/h5-8,15-17,22,25H,4,9-13H2,1-3H3/t15-,16-,17+,22?,24+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.400000000000006
  • #RotBonds: 4
  • MW: 394.5150000000001
  • HBD: 1
  • HBA: 4
  • logP: 3.6029000000000018
  • Chemical Formula: C24H30N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. pauciflora Malaysia 761086 -

External Databases


References

  • Analgesic components from bornean medicinal plants, Tabernaemontana pauciflora Blume and Tabernaemontana pandacaqui Poir. Chem Pharm Bull (Tokyo), 1992 (PMID 1423760).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Analgesic

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) -4.64
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.82
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.21
    Distribution Blood-Brain Barrier (Central Nervous System) -2.76
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.12
    Plasma Protein Binding 66.54
    Steady State Volume of Distribution 5.18
    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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.4
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.13
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.08
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.01
    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 -34.43
    Rat (Acute) 3.27
    Rat (Chronic Oral) 2.09
    Fathead Minnow 4.07
    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 466.78
    Hydration Free Energy -4.33
    Log(D) at pH=7.4 2.97
    Log(P) 2.83
    Log S -4.07
    Log(Vapor Pressure) -8.7
    Melting Point 190.16
    pKa Acid 8.89
    pKa Basic 6.47