19-Epi-heyneanine






Names

    • (1R)-1-[(1R,15R,17R,18R)-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraen-17-yl]ethanol
    • Methyl (1S,15R,17S,18S)-17-[(1R)-1-hydroxyethyl]-3,13-diazapentacyclo[13.3.1.0,.0,.0,]nonadeca-2(10),4,6,8-tetraene-1-carboxylic acid
    • CHEMBL516646
    • 19-epi-heyneanine
    • 437764-37-9
    • Methyl (1S,15R,17S,18S)-17-((1R)-1-hydroxyethyl)-3,13-diazapentacyclo(13.3.1.0,.0,.0,)nonadeca-2(10),4,6,8-tetraene-1-carboxylic acid
    • (1R)-1-((1R,15R,17R,18R)-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4,6,8-tetraen-17-yl)ethanol
    • 19-Epi-heyneanine

Attributes

  • Canonical SMILES

    C[C@H]([C@@H]1C[C@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=CC=CC=C45)O

  • InChI

    InChI=1S/C19H24N2O/c1-11(22)15-8-12-9-16-18-14(6-7-21(10-12)19(15)16)13-4-2-3-5-17(13)20-18/h2-5,11-12,15-16,19-20,22H,6-10H2,1H3/t11-,12+,15+,16+,19+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 39.260000000000005
  • #RotBonds: 1
  • MW: 296.414
  • HBD: 2
  • HBA: 2
  • logP: 2.898800000000001
  • Chemical Formula: C19H24N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. calcarea Madagascar 761054 -
    T. dichotoma Sri Lanka, Malaysia - -

External Databases


References

  • New cytotoxic indole alkaloids from Tabernaemontana calcarea from the Madagascar rainforest. J Nat Prod, 2003 (PMID 12713407).
  • Tertiary indole alkaloids from fruits of Tabernaemontana dichotoma. Planta Med, 1984 (PMID 6484030).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Spasmolytic
    • Cytotoxicity
    • 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) -5.05
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.05
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.84
    Distribution Blood-Brain Barrier (Central Nervous System) -2.98
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.41
    Plasma Protein Binding 69.03
    Steady State Volume of Distribution 3.95
    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 Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.14
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.47
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.43
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.92
    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 -1.8
    Rat (Acute) 3.09
    Rat (Chronic Oral) 1.95
    Fathead Minnow 4.07
    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 387.85
    Hydration Free Energy -5.89
    Log(D) at pH=7.4 2.03
    Log(P) 1.76
    Log S -2.66
    Log(Vapor Pressure) -7.94
    Melting Point 213.14
    pKa Acid 11.51
    pKa Basic 7.9