Heyneanine hydroxyindolenine






Names

    • 80151-98-0
    • Heyneanine hydroxy-indolenine
    • Ibogamine-18-carboxylic acid, 16,17-didehydro-9,17-dihydro-9,20-dihydroxy-, methyl ester, (4alpha,9beta,20S)-
    • DTXSID301001004
    • methyl (1S,10R,15R,17R,18S)-10-hydroxy-17-[(1S)-1-hydroxyethyl]-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2,4,6,8-tetraene-1-carboxylate
    • Methyl 9,20-dihydroxy-10,16-didehydro-9,10-dihydroibogamine-18-carboxylate
    • Heyneanine hydroxyindolenine
    • Heyneaninehydroxyindolenine
    • methyl (1S,10R,15R,17R,18S)-10-hydroxy-17-((1S)-1-hydroxyethyl)-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2,4,6,8-tetraene-1-carboxylate

Attributes

  • Canonical SMILES

    C[C@@H]([C@H]1C[C@H]2C[C@@]3([C@H]1N(C2)CC[C@@]4(C3=NC5=CC=CC=C54)O)C(=O)OC)O

  • InChI

    InChI=1S/C21H26N2O4/c1-12(24)14-9-13-10-20(19(25)27-2)17(14)23(11-13)8-7-21(26)15-5-3-4-6-16(15)22-18(20)21/h3-6,12-14,17,24,26H,7-11H2,1-2H3/t12-,13-,14+,17-,20-,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 82.36
  • #RotBonds: 2
  • MW: 370.44900000000007
  • HBD: 2
  • HBA: 6
  • logP: 1.6145999999999998
  • Chemical Formula: C21H26N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. corymbosa Malaysia, China 1679252 GK604

External Databases

    • PubChem CID: 157416
    • CAS RN: 80151-98-0

References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Cytotoxic Monoterpenoid Indole Alkaloids from Tabernaemontana corymbosa as Potent Autophagy Inhibitors by the Attenuation of Lysosomal Acidification. J Nat Prod, 2020 (PMID 32356659).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity
    • Inhibitory
    • Lysosomal acidification
    • Xanthine oxidase inhibitory

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) -4.97
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.86
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.41
    Distribution Blood-Brain Barrier (Central Nervous System) -2.57
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.63
    Plasma Protein Binding 52.99
    Steady State Volume of Distribution 3.12
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 4.04
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.43
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.56
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.49
    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 -11.91
    Rat (Acute) 3.16
    Rat (Chronic Oral) 2.0
    Fathead Minnow 4.06
    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 403.1
    Hydration Free Energy -4.35
    Log(D) at pH=7.4 1.43
    Log(P) 0.92
    Log S -2.6
    Log(Vapor Pressure) -8.81
    Melting Point 179.03
    pKa Acid 6.02
    pKa Basic 6.87