Affinine






Names

    • C09021
    • 2134-82-9
    • Q15410234
    • DTXCID90365958
    • DTXSID70415107
    • (1R,14S,15E)-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-one
    • CHEBI:2502
    • (1R,14S,15E)-15-ethylidene-18-(hydroxymethyl)-17-methyl-10,17-diazatetracyclo(12.3.1.03,11.04,9)octadeca-3(11),4,6,8-tetraen-12-one
    • Affinine
    • 17-Hydroxyvobasan-3-one

Attributes

  • Canonical SMILES

    C/C=C\1/CN([C@@H]2CC3=C(C(=O)C[C@H]1C2CO)NC4=CC=CC=C34)C

  • InChI

    InChI=1S/C20H24N2O2/c1-3-12-10-22(2)18-8-15-13-6-4-5-7-17(13)21-20(15)19(24)9-14(12)16(18)11-23/h3-7,14,16,18,21,23H,8-11H2,1-2H3/b12-3-/t14-,16?,18-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 56.330000000000005
  • #RotBonds: 1
  • MW: 324.42400000000004
  • HBD: 2
  • HBA: 3
  • logP: 2.7818000000000014
  • Chemical Formula: C20H24N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. laeta Brazil 761076 WAG
    T. macrocarpa Indonesia 761080 -

External Databases


References

  • 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).
  • Two new sarpagine-type indole alkaloids and antimalarial activity of 16-demethoxycarbonylvoacamine from Tabernaemontana macrocarpa Jack. J Nat Med, 2019 (PMID 31140017).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimalarial
    • Cytotoxicity
    • Acetylbutyrylcholinesterase 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) -4.8
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.96
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.53
    Distribution Blood-Brain Barrier (Central Nervous System) -2.41
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.71
    Plasma Protein Binding 58.13
    Steady State Volume of Distribution 4.1
    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 16.76
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.44
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.99
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.18
    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 -2.04
    Rat (Acute) 2.85
    Rat (Chronic Oral) 2.08
    Fathead Minnow 4.39
    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 424.86
    Hydration Free Energy -8.54
    Log(D) at pH=7.4 1.9
    Log(P) 2.65
    Log S -3.3
    Log(Vapor Pressure) -10.22
    Melting Point 190.29
    pKa Acid 7.96
    pKa Basic 6.31