Criofolinine






Names

    • Criofolinine

Attributes

  • Canonical SMILES

    COC([C@H]1[C@H](O)CC[C@]2([H])C1[C@]3(O)C(C4=C(C5=CC=CC=C5N4)CCN3C2=O)=O)=O

  • InChI

    InChI=1S/C21H22N2O6/c1-29-20(27)15-14(24)7-6-12-16(15)21(28)18(25)17-11(8-9-23(21)19(12)26)10-4-2-3-5-13(10)22-17/h2-5,12,14-16,22,24,28H,6-9H2,1H3/t12-,14-,15+,16?,21+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 119.92999999999998
  • #RotBonds: 1
  • MW: 398.4150000000002
  • HBD: 3
  • HBA: 6
  • logP: 0.6137999999999999
  • Chemical Formula: C21H22N2O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Criofolinine and vernavosine, new pentacyclic indole alkaloids incorporating pyrroloazepine and pyridopyrimidine moieties derived from a common yohimbine precursor. Org Lett, 2014 (PMID 25454201).

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) -5.41
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.95
    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) -3.08
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.8
    Plasma Protein Binding 53.14
    Steady State Volume of Distribution 1.85
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.74
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.21
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.18
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 3.52
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -31.57
    Rat (Acute) 4.1
    Rat (Chronic Oral) 2.9
    Fathead Minnow 4.08
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Safe
    General Properties Boiling Point 480.73
    Hydration Free Energy -6.07
    Log(D) at pH=7.4 1.62
    Log(P) 1.47
    Log S -3.07
    Log(Vapor Pressure) -10.2
    Melting Point 244.63
    pKa Acid 5.28
    pKa Basic 7.04