Hydroxyindolenine






Names

    • Hydroxyindolenine

Attributes

  • Canonical SMILES

    O=C(OC)[C@]12C3=NC4=CC(OC)=C(OC)C=C4[C@@]3(O)CCN(C5O)[C@@]1([H])[C@H](CC)C[C@H]5C2

  • InChI

    InChI=1S/C23H30N2O6/c1-5-12-8-13-11-22(21(27)31-4)18(12)25(19(13)26)7-6-23(28)14-9-16(29-2)17(30-3)10-15(14)24-20(22)23/h9-10,12-13,18-19,26,28H,5-8,11H2,1-4H3/t12-,13+,18+,19?,22+,23+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 100.82000000000001
  • #RotBonds: 4
  • MW: 430.5010000000002
  • HBD: 2
  • HBA: 8
  • logP: 1.9793999999999998
  • Chemical Formula: C23H30N2O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. chippii Ivory Coast - Lg12291
    T. dichotoma Sri Lanka, Malaysia - -
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).
  • Tertiary indole alkaloids of Tabernaemontana dichotoma seeds. Planta Med, 1983 (PMID 6635015).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Spasmolytic
    • Antimicrobial
    • Cytotoxicity

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) -5.06
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.86
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.51
    Distribution Blood-Brain Barrier (Central Nervous System) -3.12
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.73
    Plasma Protein Binding 54.16
    Steady State Volume of Distribution 1.18
    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 Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 3.08
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.05
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.36
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 9.36
    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 -74.5
    Rat (Acute) 2.67
    Rat (Chronic Oral) 1.56
    Fathead Minnow 4.12
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 449.6
    Hydration Free Energy -2.86
    Log(D) at pH=7.4 2.11
    Log(P) 0.91
    Log S -2.52
    Log(Vapor Pressure) -9.61
    Melting Point 224.04
    pKa Acid 7.68
    pKa Basic 6.59