16-Epivobasine






Names

    • Epi-16 vobasine chlorhydrate
    • 16-Epivobasine
    • (16-R)-3-Oxovobasan-17-oic acid methyl ester hydrochloride
    • 16-Epiochropamine hydrochloride
    • Vobasan-17-oic acid, 3-oxo-, methyl ester, hydrochloride, (16-R)-
    • Epi-16 ochropamine chlorhydrate
    • Ochropamine chlorhydrate
    • Vobasan-17-oic acid, 1-methyl-3-oxo-, methyl ester, hydrochloride, (16-R)-
    • 50720-31-5
    • Ochropamine chlorhydrate [French]
    • Epi-16 vobasine chlorhydrate [French]
    • (16R)-1-Methyl-3-oxovobasan-17-oic acid methyl ester hydrochloride
    • 71339-13-4
    • Ochropamine hydrochloride

Attributes

  • Canonical SMILES

    O=C(C[C@@]/1([H])[C@@]2([H])C(OC)=O)C3=C(C4=CC=CC=C4N3)C[C@]2([H])N(C)CC1=C\C

  • InChI

    InChI=1S/C21H24N2O3/c1-4-12-11-23(2)17-9-15-13-7-5-6-8-16(13)22-20(15)18(24)10-14(12)19(17)21(25)26-3/h4-8,14,17,19,22H,9-11H2,1-3H3/b12-4-/t14-,17+,19-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 62.400000000000006
  • #RotBonds: 1
  • MW: 352.43400000000014
  • HBD: 1
  • HBA: 4
  • logP: 2.9625000000000012
  • Chemical Formula: C21H24N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. corymbosa Malaysia, China 1679252 GK604

External Databases

    • PubChem CID: 6445875
    • CAS RN: 50720-31-5

References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine. J Nat Prod, 2014 (PMID 25333996).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Inhibitory
    • Cytotoxicity
    • Xanthine oxidase 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) -4.75
    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 Non-Substrate
    Skin Permeability -1.65
    Distribution Blood-Brain Barrier (Central Nervous System) -2.06
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.97
    Plasma Protein Binding 61.33
    Steady State Volume of Distribution 4.37
    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 Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 15.64
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.57
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.84
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.76
    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 -4.1
    Rat (Acute) 2.76
    Rat (Chronic Oral) 1.86
    Fathead Minnow 4.46
    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 429.22
    Hydration Free Energy -6.93
    Log(D) at pH=7.4 2.52
    Log(P) 2.9
    Log S -3.62
    Log(Vapor Pressure) -9.42
    Melting Point 204.84
    pKa Acid 8.08
    pKa Basic 5.28