Picrinine






Names

    • 2|A,5|A-Epoxy-1,2-dihydroakuammilan-17-oic acid methyl ester
    • B2703-092765
    • Methyl 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
    • Picrinine
    • 4684-32-6
    • DTXSID30425161
    • 2alpha,5alpha-Epoxy-1,2-dihydroakuammilan-17-oic acid methyl ester

Attributes

  • Canonical SMILES

    C/C=C1CN2C3C[C@@H]/1[C@H](C(OC)=O)[C@]45[C@@]3(O[C@H]2C5)NC6=CC=CC=C64

  • InChI

    InChI=1S/C20H22N2O3/c1-3-11-10-22-15-8-12(11)17(18(23)24-2)19-9-16(22)25-20(15,19)21-14-7-5-4-6-13(14)19/h3-7,12,15-17,21H,8-10H2,1-2H3/b11-3-/t12-,15?,16-,17+,19+,20+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 50.8
  • #RotBonds: 1
  • MW: 338.407
  • HBD: 1
  • HBA: 5
  • logP: 2.2458
  • Chemical Formula: C20H22N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).

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) -4.79
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.82
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.01
    Distribution Blood-Brain Barrier (Central Nervous System) -2.56
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.84
    Plasma Protein Binding 51.23
    Steady State Volume of Distribution 5.56
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 7.86
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.39
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.1
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.33
    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 -6.42
    Rat (Acute) 4.11
    Rat (Chronic Oral) 2.17
    Fathead Minnow 4.15
    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 415.58
    Hydration Free Energy -2.88
    Log(D) at pH=7.4 2.16
    Log(P) 2.25
    Log S -3.25
    Log(Vapor Pressure) -7.64
    Melting Point 198.95
    pKa Acid 8.53
    pKa Basic 6.92