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Beta-sitosterol-3-O-beta-D-glucopyranoside
- Family: Plantae - Ptaeroxylaceae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Sterol Glycoside
| Canonical Smiles | CC[C@@H](C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O[C@@H]1OC(CO)[C@H](C(C1O)O)O)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-NEOYQNEMSA-N |
| Formula | C35H60O6 |
| HBA | 6 |
| HBD | 4 |
| MW | 576.86 |
| Rotatable Bonds | 9 |
| TPSA | 99.38 |
| LogP | 5.85 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.94 |
| Exact Mass | 576.44 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Sida spinosa | Malvaceae | Plantae | 108380 |
| 2 | Ficus auriculata | Moraceae | Plantae | 100541 |
| 3 | Limonium axillare | Plumbaginaceae | Plantae | 114150 |
| 4 | Oligomeris linifolia | Resedaceae | Plantae | 265230 |
| 5 | Daucus carota subsp. carota | Apiaceae | Plantae | — |
| 6 | Centaurea africana | Asteraceae | Plantae | 2950952 |
| 7 | Sonchus macrocarpus | Asteraceae | Plantae | 2984305 |
| 8 | Terminalia brownii | Combretaceae | Plantae | 1548809 |
| 9 | Maesa lanceolata | Myrsinaceae | Plantae | 992730 |
| 10 | Kigelia africana | Bignoniaceae | Plantae | — |
| 11 | Pycnanthus angolensis | Myristicaceae | Plantae | 224864 |
| 12 | Cedrelopsis grevei | Ptaeroxylaceae | Plantae | 864332 |
Showing of synonyms
Beta-sitosterol-3-O-beta-D-glucopyranoside
Sitosteryl glucoside
Sitosterol glucoside
Sitosteryl beta-D-glucoside
(3beta)-stigmast-5-en-3-yl D-glucopyranoside
Stigmast-5-en-3beta-yl beta-D-glucopyranoside
3-O-(beta-D-glucopyranosyl)-stigmast-5-en-3beta-ol
(2R,5S)-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
(2R,5S)-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
CHEBI:187561
LMST01040197
- Seghiri R, Boumaza O, et al. (2009). A flavonoid with cytotoxic activity and other constituents from Centaurea africana. Phytochemistry Letters,2009,2(3),114-118. [View]
- Kandil FE, Ahmed KM, et al. (2000). A new flavonoid from Limonium axillare. Archiv der Pharmazie,2000,333(8),275-277. [View] [PubMed]
- Darwish FM, Reinecke MG (2003). Ecdysteroids and other constituents from Sida spinosa L. Phytochemistry,2003,62(8),1179-1184. [View] [PubMed]
- Al Fishawy A, Zayed R, et al. (2011). Phytochemical and pharmacological studies of Ficus auriculata Lour. (Moraceae) cultivated in Egypt. Planta Medica,2011,77-PL19. [View]
- Hussein SR, Elkhateeb A, et al. (2013). Phytochemical investigation of Oligomeris linifolia (Vahl) Macbr. (Resedaceae). Biochemical Systematics and Ecology,2013,49,73-76. [View]
- Machumi F, Midiwo JO, et al. (2013). Phytochemical, antimicrobial and antiplasmodial investigations of Terminalia brownii. Natural Product Communications,2013,8(6),761-764. [View] [PubMed]
- Wabo HK, Tatsimo SN, et al. (2007). Pycnanthuquinone C: a new terpenoid-quinone from Pycnanthus angolensis.. Planta medica,2007, 73(2), 187-189. [View] [PubMed]
- Ahmed AA, Bishr MM, et al. (2005). Rare trisubstituted sesquiterpenes daucanes from the wild Daucus carota. Phytochemistry,2005,66(14),1680-1684. [View] [PubMed]
- Mulholland DA, Naidoo D, et al. (2003). Secondary metabolites from Cedrelopsis grevei (Ptaeroxylaceae). Phytochemistry, 2003, 64(2), 631–635. [View]
- Manguro LO, Midiwo JO, et al. (2011). Triterpene saponins of Maesa lanceolata leaves.. Arkivoc,2011,ii,172-198. [View] [PubMed]
- Sidjui LS, Melong RR, et al. (2015). Triterpenes and Lignans from Kigelia africana. J App Pharm Sci, 2015, 5 (Suppl 2), 001-006. [View]
- Mahmoud Z, El-Masry S, et al. (1983). Two eudesmanolides from Sonchus macrocarpus. Phytochemistry,1983,22(5),1290-1291. [View]
No compound-protein relationship available.
SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC5CCCCO5
Level: 1
Mol. Weight: 576.86 g/mol
SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4
Level: 0
Mol. Weight: 576.86 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 576.86 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.15
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.92
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 1.97
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.34
- Plasma Protein Binding
- 103.6
- Steady State Volume of Distribution
- -
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
- 3.03
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.32
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.08
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.24
- 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
- -6821.82
- Rat (Acute)
- 2.64
- Rat (Chronic Oral)
- 3.23
- Fathead Minnow
- 18.15
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 359.96
- Hydration Free Energy
- -2.87
- Log(D) at pH=7.4
- 5.7
- Log(P)
- 7.42
- Log S
- -4.97
- Log(Vapor Pressure)
- -10.84
- Melting Point
- 179.26
- pKa Acid
- 8.86
- pKa Basic
- 7.71
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9023 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.9023 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8499 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8499 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8393 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8393 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7514 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7514 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7492 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7492 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7389 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7389 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7067 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7067 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7053 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7053 |