Normacusine B






Names

    • Vellosiminol
    • Tombozine
    • 124096-81-7
    • Sarpagan-17-ol
    • 8RD788YSD2
    • UNII-8RD788YSD2
    • 604-99-9
    • ((6S,7R,10R,11aS,Z)-9-ethylidene-5,6,8,9,10,11,11a,12-octahydro-6,10-methanoindolo[3,2-b]quinolizin-11-yl)methanol
    • 10-Deoxysarpagine
    • DA-67414
    • Tombozin
    • Normacusine B

Attributes

  • Canonical SMILES

    C/C=C\1/CN2[C@H]3C[C@@H]1[C@H]([C@@H]2CC4=C3NC5=CC=CC=C45)CO

  • InChI

    InChI=1S/C19H22N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,13,15,17-18,20,22H,7-10H2,1H3/b11-2-/t13-,15+,17-,18-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 39.260000000000005
  • #RotBonds: 1
  • MW: 294.398
  • HBD: 2
  • HBA: 2
  • logP: 3.0240000000000014
  • Chemical Formula: C19H22N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. chippii Ivory Coast - Lg12291
    T. laeta Brazil 761076 WAG

External Databases

    • PubChem CID: 10469722
    • CAS RN: 604-99-9

References

  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures. An Acad Bras Cienc, 2008 (PMID 18797794).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimicrobial
    • Acetylbutyrylcholinesterase inhibitory

Predicted NMR Spectral Data


Predicted MS Fragmentation Patternn


Predicted ADMET Properties

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -5.21
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.05
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.48
    Distribution Blood-Brain Barrier (Central Nervous System) -2.66
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.33
    Plasma Protein Binding 67.06
    Steady State Volume of Distribution 3.58
    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 11.85
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.14
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.16
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.73
    Micronucleos Toxic
    NR-AhR Toxic
    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 -0.34
    Rat (Acute) 2.99
    Rat (Chronic Oral) 2.24
    Fathead Minnow 4.16
    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 411.23
    Hydration Free Energy -6.46
    Log(D) at pH=7.4 1.93
    Log(P) 2.78
    Log S -3.49
    Log(Vapor Pressure) -9.12
    Melting Point 228.01
    pKa Acid 10.38
    pKa Basic 8.25