Javanuronic acid






Names

    • Javanuronic acid

Attributes

  • Canonical SMILES

    O=C1[C@@]2([C@]3(N(C(C4=CO[C@@H]([C@H]([C@]4(C3)[H])C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(O)=O)O)O)O)=O)CC2)[H])C6=C(N1)C=CC=C6

  • InChI

    InChI=1S/C26H28N2O10/c1-2-11-12-9-16-26(14-5-3-4-6-15(14)27-25(26)35)7-8-28(16)21(32)13(12)10-36-23(11)38-24-19(31)17(29)18(30)20(37-24)22(33)34/h2-6,10-12,16-20,23-24,29-31H,1,7-9H2,(H,27,35)(H,33,34)/t11-,12+,16-,17-,18-,19+,20-,23+,24-,26+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 175.09
  • #RotBonds: 4
  • MW: 528.5140000000002
  • HBD: 5
  • HBA: 9
  • logP: -0.5514999999999983
  • Chemical Formula: C26H28N2O10


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. peduncularis Thailand 761087 WU 0099055

External Databases


References

  • Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata. Molecules, 2023 (PMID 37764440).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antiproliferative
    • 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) -6.39
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.11
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 0.69
    Distribution Blood-Brain Barrier (Central Nervous System) -4.17
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.93
    Plasma Protein Binding 80.16
    Steady State Volume of Distribution 0.62
    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 Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 1.84
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life >= 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -3.55
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.3
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.9
    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 -2886.63
    Rat (Acute) 2.45
    Rat (Chronic Oral) 3.34
    Fathead Minnow 6.44
    Respiratory Disease Safe
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 486.04
    Hydration Free Energy -2.91
    Log(D) at pH=7.4 -0.93
    Log(P) -0.73
    Log S -2.65
    Log(Vapor Pressure) -13.44
    Melting Point 219.12
    pKa Acid 1.73
    pKa Basic 6.4