(3R,7S,14R,19S,20R)-19-Hydroxypseudovincadifformine






Names

    • AKOS040735261
    • 19-Hydroxypseudovincadifformine
    • (3R,7S,14R,19S,20R)-19-Hydroxypseudovincadifformine

Attributes

  • Canonical SMILES

    [H][C@]12C[C@]([C@@H](O)C)([H])CN3[C@@]1([H])[C@@]4(C5=CC=CC=C5NC4=C(C(OC)=O)C2)CC3

  • InChI

    InChI=1S/C21H26N2O3/c1-12(24)14-9-13-10-15(20(25)26-2)18-21(7-8-23(11-14)19(13)21)16-5-3-4-6-17(16)22-18/h3-6,12-14,19,22,24H,7-11H2,1-2H3/t12-,13+,14+,19+,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 61.800000000000004
  • #RotBonds: 2
  • MW: 354.4500000000002
  • HBD: 2
  • HBA: 5
  • logP: 2.2719000000000005
  • 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

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -4.96
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.09
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.54
    Distribution Blood-Brain Barrier (Central Nervous System) -2.55
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.69
    Plasma Protein Binding 42.34
    Steady State Volume of Distribution 4.23
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-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 8.21
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.45
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.74
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.12
    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 -10.93
    Rat (Acute) 3.48
    Rat (Chronic Oral) 2.37
    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 414.6
    Hydration Free Energy -7.5
    Log(D) at pH=7.4 2.13
    Log(P) 1.93
    Log S -2.19
    Log(Vapor Pressure) -7.94
    Melting Point 170.37
    pKa Acid 8.43
    pKa Basic 7.12