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Sitosterol
- Family: Plantae - Guttiferae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Phytosterol
| Canonical Smiles | COC(=O)c1c(COC(=O)C)cc2c(c1O)C(=O)c1c(C2=O)cc2c(c1O)C=CC(O2)(C)C |
|---|---|
| InChI | InChI=1S/C24H20O9/c1-10(25)32-9-11-7-13-18(21(28)16(11)23(30)31-4)22(29)17-14(19(13)26)8-15-12(20(17)27)5-6-24(2,3)33-15/h5-8,27-28H,9H2,1-4H3 |
| InChIKey | UUSLDKSHVISGDD-UHFFFAOYSA-N |
| Formula | C24H20O9 |
| HBA | 9 |
| HBD | 2 |
| MW | 452.42 |
| Rotatable Bonds | 3 |
| TPSA | 136.43 |
| LogP | 2.91 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 452.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Symphonia globulifera | Guttiferae | Plantae | 156483 |
| 2 | Vismia guineensis | Guttiferae | Plantae | 999599 |
Showing of synonyms
Sitosterol
- Tala M, Talontsi F, et al. (2013). Anthraquinones and triterpenoids from seeds of Vismia guineensis. Biochemical Systematics and Ecology, 2013, 50, 310-312. [View]
- Ngouela S, Lenta BN, et al. (2006). Anti-plasmodial and antioxidant activities of constituents of the seed shells of Symphonia globulifera Linn f.. Phytochemistry,2006, 67(3), 302-306. [View] [PubMed]
CPRiL:
2378
SMILES: O1CC=Cc(c2)c1cc(c23)C(=O)c4c(C3=O)cccc4
Level: 0
Mol. Weight: 452.42 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.09
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.570
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.58
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.850
- Plasma Protein Binding
- 40.55
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.420
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.020
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.040
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.970
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Toxic
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -81.020
- Rat (Acute)
- 2.840
- Rat (Chronic Oral)
- 3.290
- Fathead Minnow
- 5.100
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 511.710
- Hydration Free Energy
- -3.040
- Log(D) at pH=7.4
- 3.640
- Log(P)
- 4.88
- Log S
- -6.79
- Log(Vapor Pressure)
- -9.07
- Melting Point
- 212.18
- pKa Acid
- 6.61
- pKa Basic
- 3.81
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8923 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8746 |
| Pyridoxal kinase, putative | C4LVZ4 | C4LVZ4_ENTHI | Entamoeba histolytica | 3 | 0.8541 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8337 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7949 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7901 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7795 |
| 4-hydroxyphenylacetate 3-monooxygenase, reductase component | Q5SJP7 | HPAC_THET8 | Thermus thermophilus | 3 | 0.7732 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7646 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 2 | 0.7571 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7508 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7488 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7434 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7358 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7357 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7300 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7285 |
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 2 | 0.7268 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7232 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7225 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7175 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7109 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7090 |
| Phytohormone-binding protein CSBP | A0A1S3THR8 | PHBP_VIGRR | Vigna radiata var. radiata | 2 | 0.7074 |
| Metallophosphoesterase | A3DJ38 | A3DJ38_HUNT2 | Clostridium thermocellum | 2 | 0.7046 |