11-Hydroxycoronaridine






Names

    • methyl (1S,15S,17S,18S)-17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
    • 11-Hydroxycoronaridine
    • 11-hydroxycoronaridine
    • CHEMBL517789
    • methyl (1S,15S,17S,18S)-17-ethyl-6-hydroxy-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

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

  • InChI

    InChI=1S/C21H26N2O3/c1-3-13-8-12-10-21(20(25)26-2)18-16(6-7-23(11-12)19(13)21)15-5-4-14(24)9-17(15)22-18/h4-5,9,12-13,19,22,24H,3,6-8,10-11H2,1-2H3/t12-,13-,19-,21+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 65.56
  • #RotBonds: 2
  • MW: 354.4500000000001
  • HBD: 2
  • HBA: 4
  • logP: 2.9608000000000008
  • Chemical Formula: C21H26N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. calcarea Madagascar 761054 -

External Databases


References

  • New cytotoxic indole alkaloids from Tabernaemontana calcarea from the Madagascar rainforest. J Nat Prod, 2003 (PMID 12713407).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -4.81
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.14
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.33
    Distribution Blood-Brain Barrier (Central Nervous System) -2.61
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.44
    Plasma Protein Binding 56.37
    Steady State Volume of Distribution 5.06
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-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 14.28
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.2
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.06
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.02
    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 -7.46
    Rat (Acute) 2.59
    Rat (Chronic Oral) 2.32
    Fathead Minnow 3.99
    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 448.59
    Hydration Free Energy -5.99
    Log(D) at pH=7.4 2.6
    Log(P) 2.39
    Log S -3.76
    Log(Vapor Pressure) -8.93
    Melting Point 277.48
    pKa Acid 7.96
    pKa Basic 7.32