Sitosterol 3-O-beta-D-glucopyranoside - Compound Card

Sitosterol 3-O-beta-D-glucopyranoside

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Sitosterol 3-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Glucosideterpene
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-VPFCYKORSA-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 Cassia sieberiana Leguminosae/Fabaceae Plantae 1977551

Showing of synonyms

  • Atontsa BCK, Bitchagno GTM, et al. (2021). Caffeate and piperidine-3-ol derivatives from the stem bark of Cassia sieberiana.. Natural product research,2021, 35(15), 2507-2514. [View] [PubMed]
Pubchem: 12309067
Nmrshiftdb2: 60031647

No compound-protein relationship available.

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)
-5.15
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
1.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.34
Plasma Protein Binding
105.6
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
3.11
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.85
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
6.21
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
-6822.5
Rat (Acute)
2.64
Rat (Chronic Oral)
3.23
Fathead Minnow
18.11
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
362.59
Hydration Free Energy
-2.87
Log(D) at pH=7.4
5.8
Log(P)
7.37
Log S
-5.03
Log(Vapor Pressure)
-10.62
Melting Point
182.95
pKa Acid
8.81
pKa Basic
7.71
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8317
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7836
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7809
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7418
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7329
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7173
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7044

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