Stemmadenine






Names

    • DTXSID70905215
    • Stemmadenine
    • 10012-73-4
    • Methyl 5-ethylidene-7-(hydroxymethyl)-1,4,5,6,7,8-hexahydro-2H-3,6-ethanoazonino[5,4-b]indole-7-carboxylate

Attributes

  • Canonical SMILES

    C/C=C\1/CN2CC[C@H]1[C@](C3=C(CC2)C4=CC=CC=C4N3)(CO)C(=O)OC

  • InChI

    InChI=1S/C21H26N2O3/c1-3-14-12-23-10-8-16-15-6-4-5-7-18(15)22-19(16)21(13-24,20(25)26-2)17(14)9-11-23/h3-7,17,22,24H,8-13H2,1-2H3/b14-3-/t17-,21+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 65.56
  • #RotBonds: 2
  • MW: 354.4500000000001
  • HBD: 2
  • HBA: 4
  • logP: 2.3953000000000007
  • Chemical Formula: C21H26N2O3


Species

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

External Databases

    • PubChem CID: 443367
    • CAS RN: 10012-73-4

References

  • Tertiary indole alkaloids of Tabernaemontana dichotoma seeds. Planta Med, 1983 (PMID 6635015).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Spasmolytic

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

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -5.0
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.06
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.8
    Distribution Blood-Brain Barrier (Central Nervous System) -2.51
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.85
    Plasma Protein Binding 54.56
    Steady State Volume of Distribution 5.36
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor 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 11.1
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Safe
    Bioconcentration Factor -0.13
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.82
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.94
    Micronucleos Toxic
    NR-AhR Toxic
    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 -6.04
    Rat (Acute) 2.93
    Rat (Chronic Oral) 2.37
    Fathead Minnow 4.48
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 434.07
    Hydration Free Energy -7.58
    Log(D) at pH=7.4 2.51
    Log(P) 2.46
    Log S -3.23
    Log(Vapor Pressure) -9.68
    Melting Point 192.29
    pKa Acid 9.53
    pKa Basic 6.67