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3-O-beta-D-glucopyranosylstigmasterol
- Family: Plantae - Menispermaceae
- 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-/m1/s1 |
| InChIKey | VWDLOXMZIGUBKM-LUPAKLOQSA-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 | Trichilia gilletii | Menispermaceae | Plantae | 2709001 |
Showing of synonyms
3-O-beta-D-glucopyranosylstigmasterol
Stigmasterol glucoside
Stigmasterol 3-O-beta-D-glucoside
CHEMBL447335
CHEBI:68383
(2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-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
Stigmasteryl 3-beta-D-glucoside
DTXSID601289039
HY-N1200
BDBM50357395
AKOS037515192
MS44387
Stigmasterol 3-O-beta-D-glucopyranoside
Stigmasteryl-3-O-beta-D-glucopyranoside
DA-58115
MS-30354
Stigmasterol 3-O-I(2)-D-glucopyranoside
Stigma-5,22-dien-3-beta-D-glucopyranoside
CS-0016492
Stigmasta-5,22-dien-3-O-.beta.-D-glucopyranoside
Q27136880
(3beta,22E)-stigmasta-5,22-dien-3-yl beta-D-glucopyranoside
(2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(E,1R,4S)-4-ethyl-1,5-dimethyl-hex-2-enyl]-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:
6602508
Gnps:
CCMSLIB00006425432
Zinc:
ZINC000049833002
Chebi:
68383
Nmrshiftdb2:
60019895
Metabolights:
MTBLC68383
Chembl:
CHEMBL447335
Bindingdb:
50357395
CPRiL:
145727
SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC(C4)OC5CCCCO5
Level: 1
Mol. Weight: 574.84 g/mol
SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4
Level: 0
Mol. Weight: 574.84 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 574.84 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.12
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.95
- Human Oral Bioavailability 50%
- Non-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
- 105.26
- 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
- -1.85
- 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
- -6822.73
- Rat (Acute)
- 2.98
- Rat (Chronic Oral)
- 3.02
- Fathead Minnow
- 18.59
- 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
- 360.36
- Hydration Free Energy
- -2.9
- Log(D) at pH=7.4
- 5.69
- Log(P)
- 7.07
- Log S
- -5.21
- Log(Vapor Pressure)
- -10.4
- Melting Point
- 176.4
- pKa Acid
- 8.51
- pKa Basic
- 7.2
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8834 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8510 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7567 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7462 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7120 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7089 |