10-Hydroxyheyneanine






Names

    • DTXSID30228417
    • DTXCID50150908
    • Ibogamine-18-carboxylic acid, 12,20-dihydroxy-, methyl ester, (4alpha,20S)-
    • 77795-14-3
    • 10-Hydroxyheyneanine
    • methyl (1S,15R,17R,18S)-7-hydroxy-17-[(1S)-1-hydroxyethyl]-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
    • methyl (1S,15R,17R,18S)-7-hydroxy-17-((1S)-1-hydroxyethyl)-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate

Attributes

  • Canonical SMILES

    C[C@@H]([C@@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)O)C(=O)OC)O

  • InChI

    InChI=1S/C21H26N2O4/c1-11(24)15-7-12-9-21(20(26)27-2)18-14(5-6-23(10-12)19(15)21)16-8-13(25)3-4-17(16)22-18/h3-4,8,11-12,15,19,22,24-25H,5-7,9-10H2,1-2H3/t11-,12+,15-,19-,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 85.79
  • #RotBonds: 2
  • MW: 370.44900000000007
  • HBD: 3
  • HBA: 5
  • logP: 1.9316
  • Chemical Formula: C21H26N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -5.26
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.28
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.45
    Distribution Blood-Brain Barrier (Central Nervous System) -2.94
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.56
    Plasma Protein Binding 51.12
    Steady State Volume of Distribution 5.74
    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 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 10.69
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.0
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.65
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.7
    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 -10.39
    Rat (Acute) 2.83
    Rat (Chronic Oral) 2.13
    Fathead Minnow 4.1
    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 445.41
    Hydration Free Energy -6.41
    Log(D) at pH=7.4 1.76
    Log(P) 0.91
    Log S -3.14
    Log(Vapor Pressure) -9.11
    Melting Point 243.81
    pKa Acid 7.43
    pKa Basic 8.09