3-O-beta-D-glucopyranosyl beta-sitosterol - Compound Card

3-O-beta-D-glucopyranosyl beta-sitosterol

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3-O-beta-D-glucopyranosyl beta-sitosterol

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Sterol Glycoside
Canonical Smiles CC[C@@H](C(C)C)/C=C/[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/C35H58O6/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/h8-10,20-22,24-33,36-39H,7,11-19H2,1-6H3/b9-8+/t21-,22+,24-,25-,26+,27-,28-,29+,30+,31-,32+,33+,34-,35+/m0/s1
InChIKey VWDLOXMZIGUBKM-XWSLTWRZSA-N
Formula C35H58O6
HBA 6
HBD 4
MW 574.84
Rotatable Bonds 8
TPSA 99.38
LogP 5.63
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 574.42
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Pseudocedrela kotschyi Meliaceae Plantae 356281

Showing of synonyms

  • Sidjui LS, Nganso YOD, et al. (2018). Kostchyienones A and B, new antiplasmodial and cytotoxicity of limonoids from the roots of Pseudocedrela kotschyi (Schweinf.) Harms.. Zeitschrift fur Naturforschung. C, Journal of biosciences,2018, 73(3-4), 153-160. [View] [PubMed]
Pubchem: 12895781
Nmrshiftdb2: 70017022

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 574.84 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 574.84 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 574.84 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.11
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
2.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.44
Plasma Protein Binding
105.32
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
1.81
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.76
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.12
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.06
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
-6822.68
Rat (Acute)
3.0
Rat (Chronic Oral)
3.02
Fathead Minnow
18.57
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
360.43
Hydration Free Energy
-2.9
Log(D) at pH=7.4
5.66
Log(P)
7.26
Log S
-5.23
Log(Vapor Pressure)
-10.39
Melting Point
181.71
pKa Acid
8.49
pKa Basic
7.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7800
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7627
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7533
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7084
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7032
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7018

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