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Emodin 1-O-beta-D-glucoside
- Family: Plantae - Rhamnaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthraquinone Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2cc(O)cc3c2C(=O)c2c(C3=O)cc(cc2O)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C21H20O10/c1-7-2-9-14(11(24)3-7)18(27)15-10(16(9)25)4-8(23)5-12(15)30-21-20(29)19(28)17(26)13(6-22)31-21/h2-5,13,17,19-24,26,28-29H,6H2,1H3/t13-,17-,19+,20-,21-/m1/s1 |
| InChIKey | HSWIRQIYASIOBE-JNHRPPPUSA-N |
| Formula | C21H20O10 |
| HBA | 10 |
| HBD | 6 |
| MW | 432.38 |
| Rotatable Bonds | 3 |
| TPSA | 173.98 |
| LogP | -0.64 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.33 |
| Exact Mass | 432.11 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rhamnus prinoides | Rhamnaceae | Plantae | 280022 |
Showing of synonyms
Emodin 1-O-beta-D-glucoside
Emodin-8-glucoside
Emodin glucoside B
Emodin 8-O-glucoside
Emodin-1 (8)-monoglucoside
9,10-Anthracenedione, 1-(beta-D-glucopyranosyloxy)-3,8-dihydroxy-6-methyl-
UNII-YY0Q8Q1T3H
YY0Q8Q1T3H
NSC 257449
Emodin 8-beta-D-glucoside
3,8-Dihydroxy-6-methyl-1-anthraquinonyl-beta-D-glucopyranoside
NSC-257449
Glucopyranoside, 3,8-dihydroxy-6-methyl-1-anthraquinonyl-, beta-D-
EMODIN 8-O-beta-D-GLUCOSIDE
8-O-beta-D-GLUCOPYRANOSYLEMODIN
EMODIN 8-beta-D-GLUCOPYRANOSIDE
23313-21-5
Anthraglycoside B
Emodin 8-glucoside
Emodin-8-beta-D-glucoside
Emodin-8-O-beta-D-glucopyranoside
CHEBI:4783
CHEMBL464360
1,6-dihydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
52731-38-1
MFCD01725365
UNII-G2P5Y13SEK
G2P5Y13SEK
Emodin-8-glucoside (Standard)
SCHEMBL4740021
Glucopyranoside, 3,8-dihydroxy-6-methyl-1-anthraquinonyl, .beta.-D-
HY-N0311R
HY-N0311
BDBM50366683
EMODIN 8-.BETA.-D-GLUCOSIDE
LMPK13040009
AKOS037514631
EMODIN 8-O-B-D-GLUCOPYRANOSIDE
ME33279
9,10-Anthracenedione, 1-(.beta.-D-glucopyranosyloxy)-3,8-dihydroxy-6-methyl-
EMODIN 8-O-.BETA.-D-GLUCOSIDE
EMODIN-8-O-.BETA.-D-GLUCOSIDE
Emodinglucoside B (Emodin-8-glucoside)
AC-34124
AS-78826
8-O-.BETA.-D-GLUCOPYRANOSYLEMODIN
EMODIN 8-.BETA.-D-GLUCOPYRANOSIDE
DB-345562
CS-0008809
Emodin 8-glucoside, >=95% (LC/MS-UV)
EMODIN 8-O-.BETA.-D-GLUCOPYRANOSIDE
NS00094498
F17659
Q27106478
1,6-Dihydroxy-3-methyl-8-(beta-d-glucopyranosyloxy)-9,10-anthraquinone
1-beta-D-Glucopyranosyloxy-3-methyl-6-hydroxy-8-hydroxy-9,10-anthraquinone
3,8-DIHYDROXY-6-METHYL-1-ANTHRAQUINONYL-.BETA.-D-GLUCOPYRANOSIDE
9,10-Anthracenedione, 1-(|A-D-glucopyranosyloxy)-3,8-dihydroxy-6-methyl-
9,10-Anthracenedione, 1-(ss-D-glucopyranosyloxy)-3,8-dihydroxy-6-methyl-
1-(.BETA.-D-GLUCOPYRANOSYLOXY)-3,8-DIHYDROXY-6-METHYL-9,10-ANTHRACENEDIONE
1,6-Dihydroxy-3-methyl-8-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)anthracene-9,10-dione
1,6-dihydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-anthracene-9,10-dione
Pubchem:
99649
Cas:
23313-21-5
Gnps:
CCMSLIB00006716220
Zinc:
ZINC000004098672
Kegg Ligand:
C10345
Chebi:
4783
Nmrshiftdb2:
60028909
Chembl:
CHEMBL464360
Bindingdb:
50366683
CPRiL:
81004
SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3OC4CCCCO4
Level: 1
Mol. Weight: 432.38 g/mol
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 432.38 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 432.38 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.88
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.360
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -0.95
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.780
- Plasma Protein Binding
- 78.29
- 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
- Non-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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.310
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.650
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.660
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.860
- Micronucleos
- Toxic
- 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
- -39.150
- Rat (Acute)
- 2.510
- Rat (Chronic Oral)
- 4.190
- Fathead Minnow
- 4.170
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 579.180
- Hydration Free Energy
- -8.080
- Log(D) at pH=7.4
- 0.330
- Log(P)
- 0.77
- Log S
- -3.46
- Log(Vapor Pressure)
- -11.52
- Melting Point
- 189.97
- pKa Acid
- 4.76
- pKa Basic
- 5.31
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.9688 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.9688 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9148 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9148 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8939 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8939 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8818 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8818 |
| E3 ubiquitin-protein ligase Mdm2 | P56273 | MDM2_XENLA | Xenopus laevis | 3 | 0.8700 |
| E3 ubiquitin-protein ligase Mdm2 | P56273 | MDM2_XENLA | Xenopus laevis | 3 | 0.8700 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8251 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8251 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 3 | 0.8205 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 3 | 0.8205 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8201 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8201 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8196 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8196 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8164 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8164 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8123 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8123 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7988 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7988 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7860 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7860 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7856 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7856 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7749 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7749 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7705 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7705 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7688 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7688 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7686 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7686 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7626 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7626 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 3 | 0.7538 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 3 | 0.7538 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7433 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7433 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7429 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7429 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7344 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7344 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7328 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7328 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7309 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7309 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7299 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7299 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7224 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7224 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7205 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7205 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 2 | 0.7173 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 2 | 0.7173 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7167 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7167 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7148 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7148 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7108 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7108 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7107 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7107 |
| Orotidine 5'-phosphate decarboxylase | O58462 | PYRF_PYRHO | Pyrococcus horikoshii | 3 | 0.7099 |
| Orotidine 5'-phosphate decarboxylase | O58462 | PYRF_PYRHO | Pyrococcus horikoshii | 3 | 0.7099 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7084 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7084 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7083 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7083 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7064 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7064 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7040 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7040 |