10-Hydroxy-14,15-didehydrovincanmine






Names

    • 10-Hydroxy-14,15-didehydrovincanmine

Attributes

  • Canonical SMILES

    CC[C@@]12C=CC([H])N3[C@]1([H])C4=C(C5=C(C=CC(O)=C5)N4[C@@](C(OC)=O)(C2)O)CC3

  • InChI

    InChI=1S/C21H24N2O4/c1-3-20-8-4-9-22-10-7-14-15-11-13(24)5-6-16(15)23(17(14)18(20)22)21(26,12-20)19(25)27-2/h4-6,8,11,18,24,26H,3,7,9-10,12H2,1-2H3/t18-,20+,21+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 74.92999999999999
  • #RotBonds: 2
  • MW: 368.4330000000002
  • HBD: 2
  • HBA: 6
  • logP: 2.4341
  • Chemical Formula: C21H24N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bovina China, Vietnam 3036760 Cai20150423

External Databases


References

  • Vincan- and eburnan-type alkaloids from Tabernaemontana bovina and their hypoglycemic activity. Phytochemistry, 2021 (PMID 34218044).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Hypoglycemic

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) -4.89
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.92
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.92
    Distribution Blood-Brain Barrier (Central Nervous System) -2.66
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.76
    Plasma Protein Binding 46.71
    Steady State Volume of Distribution 2.45
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 12.57
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.26
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.14
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.02
    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 -10.67
    Rat (Acute) 2.79
    Rat (Chronic Oral) 1.91
    Fathead Minnow 4.03
    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 455.79
    Hydration Free Energy -7.05
    Log(D) at pH=7.4 2.18
    Log(P) 2.26
    Log S -2.99
    Log(Vapor Pressure) -9.22
    Melting Point 245.37
    pKa Acid 7.05
    pKa Basic 6.66