2′-Hydroxyvoafoline






Names

    • 2′-Hydroxyvoafoline

Attributes

  • Canonical SMILES

    CC[C@]34CC6[C@]([C@]%132C3N(CC%13)CC5C4O5)(O)N(CC7(CN(CC%12)C([C@](CC(C=CC=C%11)=C%11N%10)%12C%10=C(C(OC)=O)C9)[C@]89[C@H]7OCCC8)C6)C1=C2C=CC=C1

  • InChI

    InChI=1S/C44H52N4O5/c1-3-40-21-27-20-39(25-48-31-12-7-5-10-29(31)43(44(27,48)50)15-17-46(37(40)43)23-32-34(40)53-32)24-47-16-14-41-19-26-9-4-6-11-30(26)45-33(41)28(35(49)51-2)22-42(36(41)47)13-8-18-52-38(39)42/h4-7,9-12,27,32,34,36-38,45,50H,3,8,13-25H2,1-2H3/t27?,32?,34?,36?,37?,38-,39?,40+,41-,42-,43+,44+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 90.04
  • #RotBonds: 2
  • MW: 716.9229999999999
  • HBD: 2
  • HBA: 9
  • logP: 4.833400000000005
  • Chemical Formula: C44H52N4O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. pachysiphon Nigeria, Netherlands 403125 HXJ20171220

External Databases


References

  • Tabernaesines A-I, Cytotoxic Aspidosperma-Aspidosperma-Type Bisindole Alkaloids from Tabernaemontana pachysiphon. J Nat Prod, 2020 (PMID 33112136).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity

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) -5.63
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 88.9
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 12345.73
    Distribution Blood-Brain Barrier (Central Nervous System) -2.75
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.33
    Plasma Protein Binding 63.05
    Steady State Volume of Distribution 2.71
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-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 6.82
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -292.42
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.46
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 4.62
    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 -22409789.99
    Rat (Acute) 3.18
    Rat (Chronic Oral) 1.64
    Fathead Minnow 28289.36
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 2517962.05
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.04
    Log(P) 4.23
    Log S -5.14
    Log(Vapor Pressure) -82813.61
    Melting Point 300.03
    pKa Acid -553.05
    pKa Basic 8.1