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Beta-sitosterol-3-O-beta-D-glucoside
- Family: Plantae - Euphorbiaceae
- 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]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)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-KUENWNPSSA-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 | Eragrostis tef | Poaceae | Plantae | 110835 |
| 2 | Salix subserrata | Salicaceae | Plantae | 753747 |
| 3 | Thymelaea hirsuta | Thymelaeaceae | Plantae | 69845 |
| 4 | Aloe sinkatana | Asphodelaceae | Plantae | 210945 |
| 5 | Aloe sinkatana | Asphodelaceae | Plantae | 210945 |
| 6 | Inula crithmoides | Asteraceae | Plantae | 119182 |
| 7 | Gaillardia aristata | Asteraceae | Plantae | 55624 |
| 8 | Iphiona scabra | Asteraceae | Plantae | 211591 |
| 9 | Lactuca sativa | Asteraceae | Plantae | 4236 |
| 10 | Pulicaria laciniata | Asteraceae | Plantae | 557695 |
| 11 | Drypetes gerrardii | Euphorbiaceae | Plantae | 992685 |
Showing of synonyms
Beta-sitosterol-3-O-beta-D-glucoside
- Mahmoud ZF, Salam NAA, et al. (1981). A carotane derivative and a eudesmanolide from Inula crithmoides. Phytochemistry,1981,20(4),735-738. [View]
- El-Alfy TS, Ezzat SM, et al. (2012). Chemical and biological study of the seeds of Eragrostis tef (Zucc.) Trotter. Natural Product Research,2012,26(7),619-629. [View] [PubMed]
- Hussain H, Badawy A, et al. (2011). Chemical constituents and antimicrobial activity of Salix subserrata. Records of Natural Products,2011,5(2),133-137. [View]
- Ng’ang’a MM, Chhabra S, et al. (2008). Chemical constituents from the leaves of Drypetes gerrardii. Biochemical Systematics and Ecology,2008,36,320-322. [View] [PubMed]
- Salama MM, Kandil ZA and Islam WT. (2012). Cytotoxic compounds from the leaves of Gaillardia aristata Pursh. growing in Egypt. Natural Product Research,2012,26(22),2057-2062. [View] [PubMed]
- Rizk AM, Rimpler H (1972). Isolation of daphnoretin and beta-sitosterol-beta-D-glucoside from Thymelea hirsuta. Phytochemistry,1972,11(1),473-475. [View]
- Ghouila H, Beyaoui A, et al. (2008). Lacitemzine, a novel sesquiterpene acid from the Tunisian plant Pulicaria laciniata ( Coss. et Kral.) Thell. Tetrahedron Letters,2008,49,5721-5723. [View]
- ELhassan GOM, Adhikari A, et al. (2011). Phytochemical and biological studies on Aloe sinkatana Berger. The 14th NAPRECA Symposium and AAMPS Ethnoveterinary Medicine Symposium, At Nairobi, Kenya. August 2011. [View]
- ELhassan GOM, Adhikari A, et al. (2012). Phytochemistry and antiglycation activity of Aloe sinkatana Reynolds. Phytochemistry Letters,2012,5(4),725-728. [View]
- Mahmoud ZF, Kassem FF, et al. (1986). Sesquiterpene lactones from Lactuca sativa. Phytochemistry,1986,25(3),141-748. [View]
- El-Ghazouly MG, El-Seeakhy NA, et al. (1987). Sesquiterpene xylosides from Iphiona scabra. Phytochemistry,1987,26,439-443. [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
Cytotoxic
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%
- Non-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
- 105.34
- 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
- 3.06
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.9
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- 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
- 6.23
- 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
- -6822.75
- Rat (Acute)
- 2.64
- Rat (Chronic Oral)
- 3.23
- Fathead Minnow
- 18.1
- 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
- 363.21
- Hydration Free Energy
- -2.87
- Log(D) at pH=7.4
- 5.77
- Log(P)
- 7.34
- Log S
- -5.05
- Log(Vapor Pressure)
- -10.64
- Melting Point
- 179.17
- pKa Acid
- 8.82
- pKa Basic
- 7.72
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7378 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7378 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7322 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7322 |
| Nuclear receptor ROR-alpha | P35398 | RORA_HUMAN | Homo sapiens | 5 | 0.7304 |
| Nuclear receptor ROR-alpha | P35398 | RORA_HUMAN | Homo sapiens | 5 | 0.7304 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7095 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7095 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7051 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7051 |