Beta-sitosterol glucoside - Compound Card

Beta-sitosterol glucoside

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Beta-sitosterol glucoside

Structure
Zoomed Structure
  • Family: Plantae - Sterculiaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol Glycoside
Canonical Smiles CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(C(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
InChIKey NPJICTMALKLTFW-UHFFFAOYSA-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 Ruellia tuberosa Acanthaceae Plantae 441035
2 Oxyanthus pallidus Rubiaceae Plantae 2708921
3 Alchornea laxiflora Euphorbiaceae Plantae 316698
4 Cola lateritia Sterculiaceae Plantae 577684

Showing of synonyms

  • Siwe-Noundou X, Ndinteh D, et al. (2019). Biological activity of plant extracts and isolated compounds from Alchornea laxiflora: Anti-HIV, antibacterial and cytotoxicity evaluation. South African Journal of Botany, 2019, 122, 498-503. [View]
  • Samy MN, Khalil HE, et al. (2013). Chemical constituents from the leaves of Ruellia tuberosa. Chemistry of Natural Compounds,2013,49(1),175-176. [View]
  • Tigoufack IB, Ngnokam D, et al. (2010). Cycloartane glycosides from leaves of Oxyanthus pallidus.. Phytochemistry,2010, 71(17-18), 2182-2186. [View] [PubMed]
  • Kamdem M, Ojo O, et al. (2022). Pentacyclic Triterpenoids, Phytosteroids and Fatty Acid Isolated from the Stem-bark of Cola lateritia K. Schum. (Sterculiaceae) of Cameroon origin; Evaluation of Their Antibacterial Activity. Arabian Journal of Chemistry, 2022, 15(1), 103506. [View]
Pubchem: 12309073
Nmrshiftdb2: 60033636
CPRiL: 7215
Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 576.86 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 576.86 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 576.86 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.13
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
1.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.34
Plasma Protein Binding
25.39
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
2.86
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.04
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
Safe
Daphnia Maga
6.38
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
-6811.2
Rat (Acute)
2.65
Rat (Chronic Oral)
3.23
Fathead Minnow
18.56
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
346.64
Hydration Free Energy
-2.86
Log(D) at pH=7.4
5.37
Log(P)
7.21
Log S
-4.95
Log(Vapor Pressure)
-11.48
Melting Point
174.15
pKa Acid
8.92
pKa Basic
7.8
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 0.8270
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8270
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8083
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8083
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7686
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7686
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7487
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7487
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7236
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7236
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7236
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7236
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7126
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7126
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7091
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7091
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7071
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7071
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7010
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7010
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7008
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7008

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