10-Methoxyaffinisine






Names

    • [(1S,12S,13R,14S,15Z)-15-Ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.02,10.04,9.012,17]octadeca-2(10),4(9),5,7-tetraen-13-yl]methanol
    • 10-Methoxyaffinisine

Attributes

  • Canonical SMILES

    C/C=C/1\CN2[C@H]3C[C@H]1[C@H]([C@@H]2CC4=C3N(C5=C4C=C(C=C5)OC)C)CO

  • InChI

    InChI=1S/C21H26N2O2/c1-4-12-10-23-19-9-16-15-7-13(25-3)5-6-18(15)22(2)21(16)20(23)8-14(12)17(19)11-24/h4-7,14,17,19-20,24H,8-11H2,1-3H3/b12-4+/t14-,17-,19+,20+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 37.629999999999995
  • #RotBonds: 2
  • MW: 338.4510000000001
  • HBD: 1
  • HBA: 4
  • logP: 3.0430000000000015
  • Chemical Formula: C21H26N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. dichotoma Sri Lanka, Malaysia - -

External Databases


References

  • Vasorelaxant activity of indole alkaloids from Tabernaemontana dichotoma. J Nat Med, 2013 (PMID 22350216).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Vasorelaxant

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) -4.84
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.89
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.89
    Distribution Blood-Brain Barrier (Central Nervous System) -2.77
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.62
    Plasma Protein Binding 57.8
    Steady State Volume of Distribution 3.17
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate 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 8.62
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor 0.1
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.37
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.16
    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 -5.05
    Rat (Acute) 2.9
    Rat (Chronic Oral) 1.7
    Fathead Minnow 4.07
    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 460.24
    Hydration Free Energy -2.24
    Log(D) at pH=7.4 2.3
    Log(P) 3.01
    Log S -2.81
    Log(Vapor Pressure) -8.44
    Melting Point 189.68
    pKa Acid 10.6
    pKa Basic 8.97