Secologanoside






Names

    • 59472-23-0
    • CS-0100464
    • (2S,3R,4S)-4-(carboxymethyl)-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylic acid
    • Secologanoside (Standard)
    • MS-26494
    • (2S,3R,4S)-4-(Carboxymethyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylic acid
    • (2S,3R,4S)-4-(carboxymethyl)-3-ethenyl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-3,4-dihydro-2H-pyran-5-carboxylic acid
    • HY-N6876
    • AKOS040760115
    • Secologanoside
    • G17031
    • AC-34172
    • Secologanoside 7-methyl ester
    • DA-67516
    • HY-N6876R

Attributes

  • Canonical SMILES

    C=C[C@@H]1[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)O)CC(=O)O

  • InChI

    InChI=1S/C16H22O11/c1-2-6-7(3-10(18)19)8(14(23)24)5-25-15(6)27-16-13(22)12(21)11(20)9(4-17)26-16/h2,5-7,9,11-13,15-17,20-22H,1,3-4H2,(H,18,19)(H,23,24)/t6-,7+,9-,11-,12+,13-,15+,16+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 183.20999999999998
  • #RotBonds: 7
  • MW: 390.3410000000001
  • HBD: 6
  • HBA: 9
  • logP: -1.9791999999999978
  • Chemical Formula: C16H22O11


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

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

    • 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) -6.12
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney -6.11
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -6.79
    Distribution Blood-Brain Barrier (Central Nervous System) -3.21
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.08
    Plasma Protein Binding 74.81
    Steady State Volume of Distribution 0.46
    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 Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 3.26
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life >= 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Safe
    Bioconcentration Factor -1.52
    Biodegradation Toxic
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.09
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.25
    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 6.11
    Rat (Acute) 2.04
    Rat (Chronic Oral) 3.23
    Fathead Minnow 3.03
    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 458.2
    Hydration Free Energy -10.47
    Log(D) at pH=7.4 -2.65
    Log(P) -1.76
    Log S -0.94
    Log(Vapor Pressure) -18.96
    Melting Point 157.01
    pKa Acid 3.65
    pKa Basic 4.38