Alstrostine A






Names

    • Alstrostine A

Attributes

  • Canonical SMILES

    COC(=O)C1=CO[C@H]([C@@H]([C@@H]1C[C@H]2C(=CN3[C@H]4N2CC[C@]4(C5=CC=CC=C53)O)[C@H]6[C@H]([C@@H](OC=C6C(=O)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C=C)C=C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O

  • InChI

    InChI=1S/C44H56N2O19/c1-5-19-21(23(37(55)58-3)17-60-39(19)64-41-35(53)33(51)31(49)28(15-47)62-41)13-27-22(14-46-26-10-8-7-9-25(26)44(57)11-12-45(27)43(44)46)30-20(6-2)40(61-18-24(30)38(56)59-4)65-42-36(54)34(52)32(50)29(16-48)63-42/h5-10,14,17-21,27-36,39-43,47-54,57H,1-2,11-13,15-16H2,3-4H3/t19-,20-,21+,27+,28-,29-,30-,31-,32-,33+,34+,35-,36-,39+,40+,41+,42+,43-,44-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 296.53000000000003
  • #RotBonds: 13
  • MW: 916.9270000000006
  • HBD: 9
  • HBA: 21
  • logP: -2.321599999999991
  • Chemical Formula: C44H56N2O19


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • 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) -6.34
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 5788.47
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 757289.57
    Distribution Blood-Brain Barrier (Central Nervous System) -3.76
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.74
    Plasma Protein Binding 60.57
    Steady State Volume of Distribution 0.8
    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 Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 2.5
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life >= 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Safe
    Bioconcentration Factor -17612.06
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.34
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.05
    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 -1374443153.29
    Rat (Acute) 3.17
    Rat (Chronic Oral) 5.52
    Fathead Minnow 1734948.9
    Respiratory Disease Safe
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 154581145.53
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 -71.89
    Log(P) -1.62
    Log S -2.87
    Log(Vapor Pressure) -5090120.4
    Melting Point 228.52
    pKa Acid -37005.35
    pKa Basic -276.88