10-Hydroxy-11-methoxyvincanpusine






Names

    • 10-Hydroxy-11-methoxyvincanpusine

Attributes

  • Canonical SMILES

    CC[C@@]12[C@H](O3)[C@H](CN4[C@]1([H])C5=C(C6=C(C=C(OC)C(O)=C6)N5[C@@]3(C(OC)=O)C2)CC4)O

  • InChI

    InChI=1S/C22H26N2O6/c1-4-21-10-22(20(27)29-3)24-13-8-16(28-2)14(25)7-12(13)11-5-6-23(18(21)17(11)24)9-15(26)19(21)30-22/h7-8,15,18-19,25-26H,4-6,9-10H2,1-3H3/t15-,18+,19+,21-,22-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 93.39
  • #RotBonds: 3
  • MW: 414.4580000000002
  • HBD: 2
  • HBA: 8
  • logP: 1.6539
  • Chemical Formula: C22H26N2O6


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) -5.29
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.93
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.24
    Distribution Blood-Brain Barrier (Central Nervous System) -3.53
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.62
    Plasma Protein Binding 49.38
    Steady State Volume of Distribution 5.02
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate 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 Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 14.13
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.85
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.5
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.66
    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 -65.82
    Rat (Acute) 2.52
    Rat (Chronic Oral) 1.73
    Fathead Minnow 4.09
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 464.67
    Hydration Free Energy -3.32
    Log(D) at pH=7.4 2.14
    Log(P) 1.22
    Log S -2.71
    Log(Vapor Pressure) -10.08
    Melting Point 233.07
    pKa Acid 6.59
    pKa Basic 7.26