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Beta-sitosterol 3-O-beta-D-glucoside
- Family: Plantae - Solanaceae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Sterol Glycoside
| Canonical Smiles | CC[C@@H](C(C)C)CCC(C1CC[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-GTHRPFNOSA-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 | Lycium schweinfurthii | Solanaceae | Plantae | 416539 |
Showing of synonyms
Beta-sitosterol 3-O-beta-D-glucoside
Daucosterol
Sitogluside
474-58-8
Eleutheroside A
Alexandrin
Daucosterin
Coriandrinol
Beta-Sitosterol glucoside
BSSG
Doursterol
Sitoglusidum
Sterolin
Sitoglusido
Daucosterine
WA 184
Beta-Daucosterol
EU-4906
Sitosteryl glycoside
AW 10
Sitosterol D-glucoside
NSC-165962
BSS-G
Beta-Sitosteryl glucoside
Beta-Sitosterol monoglucoside
UNII-U45VN859W3
CHEBI:67554
AW-10
U45VN859W3
WA-184
Beta-Sitosterol D-glucoside
NSC 165962
BRN 4359450
Beta-SITOSTEROL-GLUCOSIDE
BETA-SITOSTEROL GLUCOSIDE (DAUCOSTEROL) (CONSTITUENT OF STINGING NETTLE)
(3beta)-stigmast-5-en-3-yl beta-D-glucopyranoside
Sitogluside (USAN/INN)
3-beta-(beta-D-Glucopyranosyloxy)stigmast-5-ene
Beta-sitosteryl-beta-D-glucopyranoside
.beta.-sitosterol-glucoside
CHEMBL506678
Beta-Sitosterol beta-D-Glucoside
Sitosterol-3-O-beta-D-glucoside
(2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
.beta.-D-Glucopyranoside, (3.beta.)-stigmast-5-en-3-yl
Beta-sitosterol 3-O-beta-D-glucopyranoside
(-)-beta-Sitosterol-beta-D-glucopyranoside
D05848
(2R,3R,4S,5S,6R)-2-(((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
NSC165962
Sitosterol glucuronide
B-Sitosterol b-D-glucoside
AC1NX3NW
Beta-sitosterol glucutonide
Sitogluside [USAN:INN]
Sitoglusidum [INN-Latin]
Sitoglusido [INN-Spanish]
Beta-sitosterol-beta-D-glycoside
MFCD01683621
CID5742590
EU 4906
SITOGLUSIDE [INN]
O-glucosyl-beta-sitosterol
SITOGLUSIDE [USAN]
SureCN137210
3beta-(beta-D-Glucopyranosyloxy)stigmast-5-ene
?-Sitosterol ?-D-glucoside
Ambap474-58-8
C011015
SCHEMBL137210
Sitosteryl 3-beta-D-glucoside
(3-beta)-Stigmast-5-en-3-yl-beta-D-glucopyranoside
DTXSID301045674
HY-N0410
3-O-beta-D-glucosyl-beta-sitosterol
BDBM50257635
Beta-sitosterol-beta-D-glucopyranoside
AKOS032962016
CS-5421
MS12901
-Sitosterol -D-glucoside
DA-52322
MS-30381
FT-0686600
NS00123835
.BETA.-SITOSTEROL-.BETA.-D-GLUCOSIDE
C20785
SITOSTEROL 3-O-.BETA.-D-GLUCOPYRANOSIDE
(3|A)-Stigmast-5-en-3-yl |A-D-glucopyranoside
Stigmast-5-ene, 3-beta-(beta-D-glucopyranosyloxy)-
Beta-D-Glucopyranoside, (3beta)-stigmast-5-en-3-yl
BRD-K14276241-001-01-2
Q15410900
3.BETA.-(.BETA.-D-GLUCOPYRANOSYLOXY)STIGMAST-5-ENE
BETA-SITOSTEROL GLUCOSIDE (DAUCOSTEROL) (CONSTITUENT OF STINGING NETTLE) [DSC]
(2R,3R,4S,5S,6R)-2-((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
(2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
Pubchem:
5742590
Cas:
474-58-8
Gnps:
CCMSLIB00005720278
Zinc:
ZINC000049888788
Chebi:
67554
Nmrshiftdb2:
60018815
Metabolights:
MTBLC67554
Chembl:
CHEMBL506678
Bindingdb:
50257635
CPRiL:
7215
SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC5CCCCO5
Level: 1
Mol. Weight: 576.86 g/mol
SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4
Level: 0
Mol. Weight: 576.86 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 576.86 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.14
- 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
- 1.97
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.34
- Plasma Protein Binding
- 103.94
- 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
- 3.05
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.49
- 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
- 6.24
- 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
- -6821.76
- Rat (Acute)
- 2.64
- Rat (Chronic Oral)
- 3.23
- Fathead Minnow
- 18.22
- 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
- 360.51
- Hydration Free Energy
- -2.87
- Log(D) at pH=7.4
- 5.78
- Log(P)
- 7.32
- Log S
- -5.05
- Log(Vapor Pressure)
- -10.82
- Melting Point
- 181.43
- pKa Acid
- 8.82
- pKa Basic
- 7.69
| 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 | 0.8961 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8632 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8174 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7833 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7302 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7120 |