Rupicoline






Names

    • Voaluleine
    • ZZJBUKQZGMCYEE-UHFFFAOYSA-N', "Spiro[2H-indole-2,4'-[4H-1,6]methanoquinoline]-4'a(5'H)-carboxylic acid, 8'-ethyl-1,2',3,3',6',7',8',8'a-octahydro-5-methoxy-3-oxo-, methyl ester", "Spiro[2H-indole-2,4'-[4H-1,6]methanoquinoline]-4'a(5'H)-carboxylic acid, 8'-ethyl-1,2',3,3',6',7',8',8'a-octahydro-5-methoxy-3-oxo-, methyl ester, [1'R-(1'.alpha.,4'.alpha.,4'a.beta.,6'.alpha.,8'.alpha.,8'a.beta.)]-"
    • Voacangine pseudoindoxyl
    • Voluteine
    • Voaluteine
    • Rupicoline

Attributes

  • Canonical SMILES

    CC[C@@H]1C([N@@]2C[C@@H](C1)C3)[C@]3(C(OC)=O)C4(CC2)CC5=CC(OC)=CC=C5N4

  • InChI

    InChI=1S/C22H30N2O3/c1-4-15-9-14-11-22(20(25)27-3)19(15)24(13-14)8-7-21(22)12-16-10-17(26-2)5-6-18(16)23-21/h5-6,10,14-15,19,23H,4,7-9,11-13H2,1-3H3/t14-,15-,19?,21?,22+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 50.8
  • #RotBonds: 3
  • MW: 370.49300000000005
  • HBD: 1
  • HBA: 5
  • logP: 3.0855000000000015
  • Chemical Formula: C22H30N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. australis Brazil - ICN-68457
    T. cymosa Colombia 761066 JBC3243

External Databases


References

  • Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme. Bioorg Med Chem, 2005 (PMID 15911323).
  • Molecular Human Targets of Bioactive Alkaloid-Type Compounds from Tabernaemontana cymose Jacq. Molecules, 2021 (PMID 34205626).
  • The Antiviral and Virucidal Activities of Voacangine and Structural Analogs Extracted from Tabernaemontana cymosa Depend on the Dengue Virus Strain. Plants (Basel), 2021 (PMID 34201900).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticancer
    • Antiviral
    • Antiinflammatory
    • Antioxidant
    • Anticholinesterase

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) -4.83
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.05
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.84
    Distribution Blood-Brain Barrier (Central Nervous System) -2.63
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.77
    Plasma Protein Binding 52.59
    Steady State Volume of Distribution 2.88
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate 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 Toxic
    Bee Toxic
    Bioconcentration Factor -0.57
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.2
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.49
    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 -14.5
    Rat (Acute) 3.4
    Rat (Chronic Oral) 1.79
    Fathead Minnow 3.97
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 449.0
    Hydration Free Energy -4.5
    Log(D) at pH=7.4 2.9
    Log(P) 3.05
    Log S -3.31
    Log(Vapor Pressure) -7.74
    Melting Point 207.99
    pKa Acid 8.87
    pKa Basic 7.88