Rhazimine






Names

    • 93772-08-8
    • Rhazimine
    • methyl (10R,11S,12E,18S)-12-ethylidene-17-oxo-8,14-diazapentacyclo(9.5.3.01,10.02,7.014,18)nonadeca-2,4,6,8-tetraene-10-carboxylate
    • methyl (10R,11S,12E,18S)-12-ethylidene-17-oxo-8,14-diazapentacyclo[9.5.3.01,10.02,7.014,18]nonadeca-2,4,6,8-tetraene-10-carboxylate
    • 1,17-Cyclo-1,2(1H,2H)-secoakuammilan-16-carboxylic acid, 1,17-didehydro-2-oxo-, methyl ester, (16R)-

Attributes

  • Canonical SMILES

    C/C=C\1/CN2CCC34C5=CC=CC=C5N=C[C@]3([C@H]1C[C@H]2C4=O)C(=O)OC

  • InChI

    InChI=1S/C21H22N2O3/c1-3-13-11-23-9-8-20-14-6-4-5-7-16(14)22-12-21(20,19(25)26-2)15(13)10-17(23)18(20)24/h3-7,12,15,17H,8-11H2,1-2H3/b13-3-/t15-,17-,20?,21-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 58.97
  • #RotBonds: 1
  • MW: 350.4180000000001
  • HBD: 0
  • HBA: 5
  • logP: 2.4229000000000003
  • Chemical Formula: C21H22N2O3


Species

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

External Databases

    • PubChem CID: 6443646
    • CAS RN: 93772-08-8

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) -4.85
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.64
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.32
    Distribution Blood-Brain Barrier (Central Nervous System) -2.13
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.99
    Plasma Protein Binding 61.29
    Steady State Volume of Distribution 2.21
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate 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 6.6
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.25
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.49
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.78
    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 -5.33
    Rat (Acute) 3.41
    Rat (Chronic Oral) 2.13
    Fathead Minnow 4.71
    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 427.91
    Hydration Free Energy -3.48
    Log(D) at pH=7.4 2.05
    Log(P) 1.83
    Log S -3.47
    Log(Vapor Pressure) -7.55
    Melting Point 174.06
    pKa Acid 6.4
    pKa Basic 5.27