3-O-(beta-D-glucopyranoside)-beta-sitosterol - Compound Card

3-O-(beta-D-glucopyranoside)-beta-sitosterol

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3-O-(beta-D-glucopyranoside)-beta-sitosterol

Structure
Zoomed Structure
  • Family: Plantae - Primulaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol
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](OC)[C@H]([C@@H]([C@H]1O)O)O)C
InChI InChI=1S/C35H60O6/c1-8-22(20(2)3)10-9-21(4)26-13-14-27-25-12-11-23-19-24(15-17-34(23,5)28(25)16-18-35(26,27)6)40-33-31(38)29(36)30(37)32(39-7)41-33/h11,20-22,24-33,36-38H,8-10,12-19H2,1-7H3/t21-,22-,24+,25+,26-,27+,28+,29+,30+,31-,32+,33-,34+,35-/m1/s1
InChIKey QHKKPRDTANXCBJ-RRTUNWSWSA-N
Formula C35H60O6
HBA 6
HBD 3
MW 576.86
Rotatable Bonds 9
TPSA 88.38
LogP 6.46
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 Maesa lanceolata Primulaceae Plantae 992730

Showing of synonyms

  • Seumo AS, Nanfack ARD, et al. (2022). Alkenylbenzoquinones and other compounds from the fruit of Maesa lanceolata exhibited potent cytotoxic, antibacterial, and antiradical scavenging activities.. Natural product research,2022, 36(17), 4379-4387. [View] [PubMed]
Pubchem: 162971118
Nmrshiftdb2: 60059728

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)
-4.98
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.85
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.34
Plasma Protein Binding
103.88
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
5.06
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.14
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.11
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.85
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
-6822.69
Rat (Acute)
2.47
Rat (Chronic Oral)
3.01
Fathead Minnow
18.63
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
347.27
Hydration Free Energy
-2.86
Log(D) at pH=7.4
5.9
Log(P)
7.82
Log S
-5.42
Log(Vapor Pressure)
-11.54
Melting Point
178.63
pKa Acid
8.93
pKa Basic
7.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8336
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7590
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7425
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7416
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7308
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7292

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