Spegatrine






Names

    • Q15427854
    • (1S,13R,14S,15E)-15-ethylidene-13-(hydroxymethyl)-17-methyl-3-aza-17-azoniapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4(9),5,7-tetraen-7-ol
    • AKOS032948989
    • Spegatrine
    • SCHEMBL25365744
    • Sarpaganium, 10,17-dihydroxy-4-methyl-
    • (1S,13R,14S,15E)-15-ethylidene-13-(hydroxymethyl)-17-methyl-3-aza-17-azoniapentacyclo(12.3.1.02,10.04,9.012,17)octadeca-2(10),4(9),5,7-tetraen-7-ol
    • 47326-53-4

Attributes

  • Canonical SMILES

    C/C=C\1/C[N+]2([C@H]3C[C@H]1[C@H](C2CC4=C3NC5=C4C=C(C=C5)O)CO)C

  • InChI

    InChI=1S/C20H24N2O2/c1-3-11-9-22(2)18-8-15-14-6-12(24)4-5-17(14)21-20(15)19(22)7-13(11)16(18)10-23/h3-6,13,16,18-19,21,23H,7-10H2,1-2H3/p+1/b11-3-/t13-,16-,18?,19+,22?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 56.25
  • #RotBonds: 1
  • MW: 325.432
  • HBD: 3
  • HBA: 2
  • logP: 2.8742
  • Chemical Formula: C20H25N2O2+


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. contorta Cameroon 761060 N43440/HNC

External Databases


References

  • Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae). Nat Prod Res, 2021 (PMID 31274013).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticolon cancer

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) -5.53
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.17
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.12
    Distribution Blood-Brain Barrier (Central Nervous System) -3.26
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.19
    Plasma Protein Binding 48.37
    Steady State Volume of Distribution 2.13
    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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 15.67
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor 0.64
    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 5.56
    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 0.01
    Rat (Acute) 2.87
    Rat (Chronic Oral) 2.21
    Fathead Minnow 4.36
    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 451.73
    Hydration Free Energy -7.22
    Log(D) at pH=7.4 0.7
    Log(P) -0.94
    Log S -1.55
    Log(Vapor Pressure) -11.54
    Melting Point 325.34
    pKa Acid 7.9
    pKa Basic 7.01