Sitosterol-3-O-β-D-glucopyranoside






Names

    • (2R,3R,4S,5S,6R)-2-(((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
    • sitosteryl 3-beta-D-glucoside
    • C20785
    • Daucosterol
    • Doursterol
    • NSC165962
    • Q-100502
    • Daucosterine
    • beta-sitosterol glucutonide
    • beta-Sitosterol beta-D-Glucoside
    • Q15410900
    • BSS-G
    • beta-Sitosterol D-glucoside
    • beta-SITOSTEROL-GLUCOSIDE
    • EU-4906
    • (3beta)-stigmast-5-en-3-yl beta-D-glucopyranoside
    • Sitosterol D-glucoside
    • Stigmast-5-ene, 3-beta-(beta-D-glucopyranosyloxy)-
    • NSC 165962
    • UNII-U45VN859W3
    • (-)-beta-Sitosterol-beta-D-glucopyranoside
    • Coriandrinol
    • Ambap474-58-8
    • FT-0686600
    • .beta.-D-Glucopyranoside, (3.beta.)-stigmast-5-en-3-yl
    • (3-beta)-Stigmast-5-en-3-yl-beta-D-glucopyranoside
    • Daucosterin
    • Eleutheroside A
    • BRD-K14276241-001-01-2
    • 3beta-(beta-D-Glucopyranosyloxy)stigmast-5-ene
    • (2R,3R,4S,5S,6R)-2-((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
    • WA-184
    • Sitogluside (USAN/INN)
    • beta-sitosterol-beta-D-glycoside
    • beta-sitosterol 3-O-beta-D-glucoside
    • Eleutheroside A;-Sitosterol -D-glucoside
    • beta-sitosterol 3-O-beta-D-glucopyranoside
    • Sitoglusido
    • EU 4906
    • DTXSID301045674
    • DA-52322
    • CHEBI:67554
    • .BETA.-SITOSTEROL-.BETA.-D-GLUCOSIDE
    • (2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
    • BDBM50257635
    • beta-sitosterol-beta-D-glucopyranoside
    • U45VN859W3
    • Sitoglusidum [INN-Latin]
    • O-glucosyl-beta-sitosterol
    • Eleutheroside A
    • HY-N0410
    • BETA-SITOSTEROL GLUCOSIDE (DAUCOSTEROL) (CONSTITUENT OF STINGING NETTLE)
    • SureCN137210
    • Sitosterol-3-O-β-D-glucopyranoside
    • NS00123835
    • .beta.-sitosterol-glucoside
    • beta-Sitosterol glucoside
    • Sterolin
    • Alexandrin
    • AKOS032962016
    • AW 10
    • beta-Sitosterol monoglucoside
    • Sitosterol-3-O-beta-D-glucoside
    • CID5742590
    • beta-sitosteryl-beta-D-glucopyranoside
    • SITOGLUSIDE [INN]
    • NSC-165962
    • beta-D-Glucopyranoside, (3beta)-stigmast-5-en-3-yl
    • MS-30381
    • AC1NX3NW
    • 3.BETA.-(.BETA.-D-GLUCOPYRANOSYLOXY)STIGMAST-5-ENE
    • SITOSTEROL 3-O-.BETA.-D-GLUCOPYRANOSIDE
    • 474-58-8
    • AW-10
    • D05848
    • 3-beta-(beta-D-Glucopyranosyloxy)stigmast-5-ene
    • beta-Daucosterol
    • 3-O-beta-D-glucosyl-beta-sitosterol
    • Sitoglusido [INN-Spanish]
    • CS-5421
    • beta-Sitosteryl glucoside
    • (2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
    • b-Sitosterol b-D-glucoside
    • SITOGLUSIDE [USAN]
    • C011015
    • WA 184
    • Sitosteryl glycoside
    • MFCD01683621
    • Sitogluside [USAN:INN]
    • CHEMBL506678
    • sitosterol glucuronide
    • BSSG
    • Sitoglusidum
    • SCHEMBL137210
    • Sitogluside
    • BETA-SITOSTEROL GLUCOSIDE (DAUCOSTEROL) (CONSTITUENT OF STINGING NETTLE) [DSC]
    • BRN 4359450

Attributes

  • Canonical SMILES

    CC[C@@H](C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]3[C@H]2CC=C4[C@]3(C)CC[C@H](O[C@H]5[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O5)C4)C

  • InChI

    InChI=1S/C35H60O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h10,20-22,24-33,36-39H,7-9,11-19H2,1-6H3/t21-,22-,24+,25+,26-,27+,28+,29-,30-,31+,32-,33-,34+,35-/m1/s1

  • Molecule Class: Minor compounds
  • TPSA: 99.38000000000001
  • #RotBonds: 9
  • MW: 576.8590000000002
  • HBD: 4
  • HBA: 6
  • logP: 5.849000000000009
  • Chemical Formula: C35H60O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. contorta Cameroon 761060 N43440/HNC
    T. inconspicua Cameroon 761075 NHC61026

External Databases


References

  • A New Antimicrobial Phenylpropanol from the Leaves of Tabernaemontana inconspicua Stapf. (Apocynaceae) Inhibits Pathogenic Gram-Negative Bacteria. Antibiotics (Basel), 2022 (PMID 35052998).
  • Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae). Nat Prod Res, 2021 (PMID 31274013).

Compound-Protein Relationships


Compound Activities

    • Antimicrobial
    • Anticolon cancer

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) -5.15
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.92
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability 1.98
    Distribution Blood-Brain Barrier (Central Nervous System) -3.18
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.34
    Plasma Protein Binding 105.41
    Steady State Volume of Distribution 0.79
    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 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 3.08
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -1.91
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.08
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 6.21
    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 -6822.77
    Rat (Acute) 2.63
    Rat (Chronic Oral) 3.23
    Fathead Minnow 18.1
    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 363.32
    Hydration Free Energy -2.87
    Log(D) at pH=7.4 5.78
    Log(P) 7.19
    Log S -5.04
    Log(Vapor Pressure) -10.64
    Melting Point 175.34
    pKa Acid 8.84
    pKa Basic 7.74