NPs Basic Information

Name
Sitogluside
Molecular Formula C35H60O6
IUPAC Name*
(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
SMILES
CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)C(C)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
InChIKey
NPJICTMALKLTFW-OFUAXYCQSA-N
Synonyms
Daucosterol; Sitogluside; 474-58-8; Eleutheroside A; Alexandrin; Daucosterin; Coriandrinol; beta-Sitosterol glucoside; BSSG; Sitoglusidum; Doursterol; Sterolin; WA 184; Daucosterine; EU-4906; beta-Daucosterol; AW 10; Eleutheroside A; NSC-165962; BSS-G; Sitogluside (USAN/INN); 3-beta-(beta-D-Glucopyranosyloxy)stigmast-5-ene; beta-sitosteryl-beta-D-glucopyranoside; .beta.-sitosterol-glucoside; CHEMBL506678; CHEBI:67554; Sitosterol-3-O-beta-D-glucoside; AW-10; U45VN859W3; (3beta)-stigmast-5-en-3-yl beta-D-glucopyranoside; WA-184; .beta.-D-Glucopyranoside, (3.beta.)-stigmast-5-en-3-yl; beta-sitosterol 3-O-beta-D-glucopyranoside; (-)-beta-Sitosterol-beta-D-glucopyranoside; D05848; (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; Sitoglusido; NSC165962; Sitosteryl glycoside; sitosterol glucuronide; Sitosterol D-glucoside; beta-Sitosteryl glucoside; AC1NX3NW; beta-sitosterol glucutonide; Sitogluside [USAN:INN]; Sitoglusidum [INN-Latin]; Sitoglusido [INN-Spanish]; beta-Sitosterol beta-D-Glucoside; beta-Sitosterol monoglucoside; UNII-U45VN859W3; beta-sitosterol-beta-D-glycoside; FT-0686600; CID5742590; NSC 165962; EU 4906; BRN 4359450; SITOGLUSIDE [INN]; O-glucosyl-beta-sitosterol; SITOGLUSIDE [USAN]; SureCN137210; 3beta-(beta-D-Glucopyranosyloxy)stigmast-5-ene; b-Sitosterol b-D-glucoside; beta-Sitosterol D-glucoside; Ambap474-58-8; C011015; SCHEMBL137210; sitosteryl 3-beta-D-glucoside; (3-beta)-Stigmast-5-en-3-yl-beta-D-glucopyranoside; DTXSID301045674; HY-N0410; 3-O-beta-D-glucosyl-beta-sitosterol; BDBM50257635; MFCD01683621; ZINC49888788; beta-sitosterol 3-O-beta-D-glucoside; beta-sitosterol-beta-D-glucopyranoside; AKOS032962016; CS-5421; .BETA.-SITOSTEROL-.BETA.-D-GLUCOSIDE; C20785; SITOSTEROL 3-O-.BETA.-D-GLUCOPYRANOSIDE; 474D588; Q-100502; Stigmast-5-ene, 3-beta-(beta-D-glucopyranosyloxy)-; beta-D-Glucopyranoside, (3beta)-stigmast-5-en-3-yl; Q15410900; 3.BETA.-(.BETA.-D-GLUCOPYRANOSYLOXY)STIGMAST-5-ENE; BETA-SITOSTEROL GLUCOSIDE (DAUCOSTEROL) (CONSTITUENT OF STINGING NETTLE) [DSC]; (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; (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
CAS 474-58-8
PubChem CID 5742590
ChEMBL ID CHEMBL506678
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Lipids and lipid-like mol
      • Class: Steroids and steroid deri
        • Subclass: Stigmastanes and derivati
          • Direct Parent: Stigmastanes and derivati

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

NPs Physi-Chem Properties

Molecular Weight: 576.8 ALogp: 7.7
HBD: 4 HBA: 6
Rotatable Bonds: 9 Lipinski's rule of five: Rejected
Polar Surface Area: 99.4 Aromatic Rings: 5
Heavy Atoms: 41 QED Weighted: 0.253

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.793 MDCK Permeability: 0.00001170
Pgp-inhibitor: 0.982 Pgp-substrate: 0.14
Human Intestinal Absorption (HIA): 0.01 20% Bioavailability (F20%): 0.901
30% Bioavailability (F30%): 0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.01 Plasma Protein Binding (PPB): 92.30%
Volume Distribution (VD): 1.125 Fu: 1.85%

ADMET: Metabolism

CYP1A2-inhibitor: 0.021 CYP1A2-substrate: 0.341
CYP2C19-inhibitor: 0.024 CYP2C19-substrate: 0.776
CYP2C9-inhibitor: 0.124 CYP2C9-substrate: 0.05
CYP2D6-inhibitor: 0.014 CYP2D6-substrate: 0.118
CYP3A4-inhibitor: 0.271 CYP3A4-substrate: 0.353

ADMET: Excretion

Clearance (CL): 3.083 Half-life (T1/2): 0.131

ADMET: Toxicity

hERG Blockers: 0.891 Human Hepatotoxicity (H-HT): 0.163
Drug-inuced Liver Injury (DILI): 0.179 AMES Toxicity: 0.015
Rat Oral Acute Toxicity: 0.005 Maximum Recommended Daily Dose: 0.049
Skin Sensitization: 0.938 Carcinogencity: 0.098
Eye Corrosion: 0.005 Eye Irritation: 0.099
Respiratory Toxicity: 0.89
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC001889 0.794 D0Y7LD 0.675
ENC001107 0.675 D07ORO 0.410
ENC001008 0.675 D0B4RU 0.394
ENC001647 0.659 D0M4WA 0.383
ENC000961 0.582 D04RYU 0.379
ENC004803 0.559 D0G3SH 0.357
ENC001475 0.555 D03ZTE 0.357
ENC000125 0.553 D0S0NK 0.344
ENC001942 0.543 D0K0EK 0.333
ENC001170 0.540 D0OR2L 0.324
*Note: the compound similarity was calculated by RDKIT.