Dichomine






Names

    • 89647-74-5
    • Dichomine
    • (13R,14R,16R)-14-ethyl-19-oxa-2,12-diazahexacyclo[12.4.1.112,16.01,9.03,8.09,13]icosa-3,5,7-triene
    • (13R,14R,16R)-14-ethyl-19-oxa-2,12-diazahexacyclo(12.4.1.112,16.01,9.03,8.09,13)icosa-3,5,7-triene
    • DTXSID901008915', "5H-2,4a-Ethano-1H-indolizino(1',8':3,4,5)furo- (2,3-b)indole,3a-ethyl-,3,3a,10,11,12ahexahydro-,(2S,3aR,4aS,9bR,12aR)-", "3a-Ethyl-2,3,3a,10,11,12a-hexahydro-1H,5H-2,4a-ethanoindolizino[1',8':3,4,5]furo[2,3-b]indole", "5H-2,4a-Ethano-1H-indolizino(1',8':3,4,5)furo-(2,3-b)indole,3a-ethyl-,3,3a,10,11,12ahexahydro-,(2S,3aR,4aS,9bR,12aR)-"

Attributes

  • Canonical SMILES

    CC[C@]12C[C@H]3CCC4(O1)C5([C@H]2N(C3)CC5)C6=CC=CC=C6N4

  • InChI

    InChI=1S/C19H24N2O/c1-2-17-11-13-7-8-19(22-17)18(9-10-21(12-13)16(17)18)14-5-3-4-6-15(14)20-19/h3-6,13,16,20H,2,7-12H2,1H3/t13-,16+,17-,18?,19?/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 24.5
  • #RotBonds: 1
  • MW: 296.414
  • HBD: 1
  • HBA: 3
  • logP: 3.113200000000001
  • Chemical Formula: C19H24N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. dichotoma Sri Lanka, Malaysia - -
    T. eglandulosa Sri Lanka, Malaysia 761067 -

External Databases


References

  • Dichomine, a novel type of iboga alkaloid*,**. Planta Med, 1983 (PMID 17405059).
  • Tertiary indole alkaloids from fruits of Tabernaemontana dichotoma. Planta Med, 1984 (PMID 6484030).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Spasmolytic
    • Convulsive

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) -4.81
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.16
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.09
    Distribution Blood-Brain Barrier (Central Nervous System) -2.73
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.5
    Plasma Protein Binding 32.08
    Steady State Volume of Distribution 3.19
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-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 Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.34
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.14
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.02
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.87
    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 -0.36
    Rat (Acute) 3.39
    Rat (Chronic Oral) 1.47
    Fathead Minnow 4.01
    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 380.22
    Hydration Free Energy -4.16
    Log(D) at pH=7.4 2.11
    Log(P) 2.96
    Log S -2.13
    Log(Vapor Pressure) -7.33
    Melting Point 152.91
    pKa Acid 11.24
    pKa Basic 7.88