Iboluteine






Names

    • Voaluteine, 18-de(methoxycarbonyl)-
    • Ibogaine pseudoindoxyl
    • Iboluteine
    • DQOMBBVESFBJLX-UHFFFAOYSA-N
    • NS00121111', "8'-Ethyl-5-methoxy-2',3',4'a,5',6',7',8',8'a-octahydrospiro[indole-2,4'-[1,6]methanoquinolin]-3(1H)-one", "Spiro[2H-indole-2,4'-[4H-1,6]methanoquinolin]-3(1H)-one, 8'-ethyl-2',3',4'a,5',6',7',8',8'a-octahydro-5-methoxy-", "Spiro[2H-indole-2,4'-[4H-1,6]methanoquinolin]-3(1H)-one, 8'-ethyl-2',3',4'a,5',6',7',8',8'a-octahydro-5-methoxy-, (1'R,2R,4'aS,6'S,8'R,8'aR)-", "Spiro[2H-indole-2,4'-[4H-1,6]methanoquinolin]-3(1H)-one, 8'-ethyl-2',3',4'a,5',6',7',8',8'a-octahydro-5-methoxy-, [1'R-(1'.alpha.,4'.alpha.,4'a.beta.,6'.alpha.,8'.alpha.,8'a.beta.)]-"
    • 468-11-1
    • DTXSID70963658

Attributes

  • Canonical SMILES

    CC[C@@H]1C[C@H]2C[C@H]3[C@@H]1N(C2)CC[C@]34C(=O)C5=C(N4)C=CC(=C5)OC

  • InChI

    InChI=1S/C20H26N2O2/c1-3-13-8-12-9-16-18(13)22(11-12)7-6-20(16)19(23)15-10-14(24-2)4-5-17(15)21-20/h4-5,10,12-13,16,18,21H,3,6-9,11H2,1-2H3/t12-,13+,16-,18+,20+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 41.57000000000001
  • #RotBonds: 2
  • MW: 326.44
  • HBD: 1
  • HBA: 4
  • logP: 3.182500000000001
  • Chemical Formula: C20H26N2O2


Species

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

External Databases


References

  • Iboga-type alkaloids with Indolizidino[8,7-b]Indole scaffold and bisindole alkaloids from Tabernaemontana bufalina Lour. Phytochemistry, 2022 (PMID 35074605).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • α-glucosidase inhibitory
    • Butyrylcholinesterase
    • Antimicrobial

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) -4.71
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.9
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.99
    Distribution Blood-Brain Barrier (Central Nervous System) -2.74
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.61
    Plasma Protein Binding 60.46
    Steady State Volume of Distribution 2.26
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate 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 9.5
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.47
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.32
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.4
    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 Toxic
    T. Pyriformis -1.98
    Rat (Acute) 3.23
    Rat (Chronic Oral) 1.71
    Fathead Minnow 3.72
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 437.13
    Hydration Free Energy -4.75
    Log(D) at pH=7.4 2.24
    Log(P) 3.0
    Log S -3.18
    Log(Vapor Pressure) -7.92
    Melting Point 187.9
    pKa Acid 7.82
    pKa Basic 8.45