Quebrachitol






Names

    • (1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol
    • 9W4JLQ7I4W
    • Brahol
    • NSC-26254
    • L-Quebrachitol
    • DSCFFEYYQKSRSV-FIZWYUIZSA-N
    • D-chiro-Inositol, 2-O-methyl-
    • 2-O-Methyl-L-chiro-inositol
    • Inositol, 2-O-methyl-
    • L-(-)-2-O-Methylinositol
    • 642-38-6
    • Inositol, 2-O-methyl-, L-chiro-
    • NSC-131046
    • 2B678708-4698-466E-88D8-3443A058E849
    • HY-N2375
    • 2-O-Methyl-chiro-inositol
    • L-chiro-Inositol, 2-O-methyl-
    • (1R,2S,3S,4S,5R,6R)-6-Methoxycyclohexane-1,2,3,4,5-pentaol
    • DA-75114
    • DTXSID601029528
    • Q7269871
    • UNII-9W4JLQ7I4W
    • MFCD00021405
    • 6-methoxycyclohexane-1,2,3,4,5-pentol
    • 2-O-methyl-L-chiro-inositol; Brahol; Quebrachit
    • Quebrachit
    • s3223
    • SCHEMBL240345
    • Pinitol TMS
    • (-)-Quebrachitol
    • DTXSID80957028
    • CHEMBL501109
    • C08257
    • M02437
    • CHEBI:170050
    • 3564-07-6
    • DSCFFEYYQKSRSV-MBXCVVGISA-N
    • W-203384
    • AKOS027327479
    • 1L-2-O-methyl-chiro-inositol
    • Quebrachitol, L-
    • CS-0022555
    • Quebrachitol
    • MS-23047
    • SCHEMBL22975188
    • CHEBI:111
    • Quebrachitol, (-)-

Attributes

  • Canonical SMILES

    CO[C@H]1[C@H](O)C(O)[C@H](O)[C@H](O)[C@H]1O

  • InChI

    InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3+,4?,5-,6-,7-/m1/s1

  • Molecule Class: Minor compounds
  • TPSA: 110.38000000000001
  • #RotBonds: 1
  • MW: 194.18300000000002
  • HBD: 5
  • HBA: 6
  • logP: -3.1805
  • Chemical Formula: C7H14O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. ventricosa Kenya 761103 AM2017/04

External Databases


References

  • Antileishmanial and cytotoxic activity of secondary metabolites from Taberneamontana ventricosa and two aloe species. Nat Prod Res, 2022 (PMID 33459049).

Compound-Protein Relationships


Compound Activities

    • Antileishmanial
    • 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) -5.07
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -3.33
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.34
    Distribution Blood-Brain Barrier (Central Nervous System) -4.26
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.43
    Plasma Protein Binding 39.45
    Steady State Volume of Distribution 0.2
    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 1.9
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life >= 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.53
    Biodegradation Toxic
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 2.63
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 3.39
    Micronucleos Safe
    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 -2.95
    Rat (Acute) 1.16
    Rat (Chronic Oral) 3.28
    Fathead Minnow 0.82
    Respiratory Disease Safe
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 378.9
    Hydration Free Energy -23.94
    Log(D) at pH=7.4 -2.42
    Log(P) -2.78
    Log S -0.46
    Log(Vapor Pressure) -13.07
    Melting Point 167.01
    pKa Acid 8.28
    pKa Basic 5.27