Picraline






Names

    • 2671-32-1
    • Picraline
    • B0005-458088
    • methyl (1R,9S,11S,14E,15S,17S,19R)-19-(acetyloxymethyl)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1^{9,15.0^{1,9.0^{3,8.0^{12,17]nonadeca-3,5,7-triene-19-carboxylate
    • methyl 19-(acetyloxymethyl)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.19,15.01,9.03,8.012,17]nonadeca-3,5,7-triene-19-carboxylate

Attributes

  • Canonical SMILES

    C/C=C1[C@@]2([H])C[C@@H]3C4(O5)NC6=CC=CC=C6[C@@]4(C2(C(OC)=O)COC(C)=O)CC5N3C/1

  • InChI

    InChI=1S/C23H26N2O5/c1-4-14-11-25-18-9-16(14)21(20(27)28-3,12-29-13(2)26)22-10-19(25)30-23(18,22)24-17-8-6-5-7-15(17)22/h4-8,16,18-19,24H,9-12H2,1-3H3/b14-4+/t16-,18-,19?,21?,22-,23?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 77.10000000000001
  • #RotBonds: 3
  • MW: 410.47000000000025
  • HBD: 1
  • HBA: 7
  • logP: 2.1791
  • Chemical Formula: C23H26N2O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. chippii Ivory Coast - Lg12291

External Databases


References

  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimicrobial

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 -4.87
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.31
    Distribution Blood-Brain Barrier (Central Nervous System) -2.5
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.07
    Plasma Protein Binding 50.82
    Steady State Volume of Distribution 3.38
    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 Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.84
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.18
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.35
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.49
    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 -74.95
    Rat (Acute) 3.77
    Rat (Chronic Oral) 2.01
    Fathead Minnow 4.24
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 441.21
    Hydration Free Energy -2.31
    Log(D) at pH=7.4 2.25
    Log(P) 1.97
    Log S -3.59
    Log(Vapor Pressure) -8.37
    Melting Point 193.34
    pKa Acid 8.1
    pKa Basic 5.26