17-Demethoxy-isorhynchophylline






Names

    • 17-Demethoxy-isorhynchophylline

Attributes

  • Canonical SMILES

    CC[C@H]1CN2CC[C@]3(C4=CC=CC=C4NC3=O)[C@]2([H])C[C@@H]1C(C(OC)=O)=C

  • InChI

    InChI=1S/C21H26N2O3/c1-4-14-12-23-10-9-21(16-7-5-6-8-17(16)22-20(21)25)18(23)11-15(14)13(2)19(24)26-3/h5-8,14-15,18H,2,4,9-12H2,1,3H3,(H,22,25)/t14-,15+,18-,21-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 58.64000000000001
  • #RotBonds: 3
  • MW: 354.4500000000002
  • HBD: 1
  • HBA: 4
  • logP: 2.7261000000000006
  • Chemical Formula: C21H26N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases


References

  • Chemical Constituents from Tabernaemontana bufalina Lour. Chem Biodivers, 2019 (PMID 30411487).

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) -4.66
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.84
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.72
    Distribution Blood-Brain Barrier (Central Nervous System) -2.52
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.68
    Plasma Protein Binding 57.33
    Steady State Volume of Distribution 4.27
    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 Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.09
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.63
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.67
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.04
    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 -5.42
    Rat (Acute) 3.57
    Rat (Chronic Oral) 2.14
    Fathead Minnow 4.01
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 399.47
    Hydration Free Energy -5.3
    Log(D) at pH=7.4 2.73
    Log(P) 2.62
    Log S -3.09
    Log(Vapor Pressure) -7.75
    Melting Point 183.71
    pKa Acid 7.9
    pKa Basic 7.27