Anhydrovobasindiol






Names

    • Anhydrovobasindiol

Attributes

  • Canonical SMILES

    C/C=C1[C@]2([H])CC3C4=C(C5=C(C=CC=C5)N4)C[C@@](N(C\1)C)([H])C2CO3

  • InChI

    InChI=1S/C20H24N2O/c1-3-12-10-22(2)18-8-15-13-6-4-5-7-17(13)21-20(15)19-9-14(12)16(18)11-23-19/h3-7,14,16,18-19,21H,8-11H2,1-2H3/b12-3-/t14-,16?,18-,19?/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 28.26
  • #RotBonds: 0
  • MW: 308.42500000000007
  • HBD: 1
  • HBA: 2
  • logP: 3.6781000000000024
  • Chemical Formula: C20H24N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. chippii Ivory Coast - Lg12291

External Databases


References

  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -4.84
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.07
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.87
    Distribution Blood-Brain Barrier (Central Nervous System) -2.16
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.66
    Plasma Protein Binding 52.14
    Steady State Volume of Distribution 4.0
    Metabolism Breast Cancer Resistance Protein 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 15.4
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 2.62
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.37
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.45
    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 -0.63
    Rat (Acute) 2.89
    Rat (Chronic Oral) 1.58
    Fathead Minnow 4.4
    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 388.71
    Hydration Free Energy -6.64
    Log(D) at pH=7.4 2.37
    Log(P) 3.88
    Log S -3.51
    Log(Vapor Pressure) -8.65
    Melting Point 166.63
    pKa Acid 10.76
    pKa Basic 8.36