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Chrysophanol-8-mono-beta-D-glucoside
- Family: Plantae - Liliaceae
- Kingdom: Plantae
-
Class: Anthracene
- Subclass: Anthraquinone Glucoside
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2cccc3c2C(=O)c2c(C3=O)cc(cc2O)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C21H20O9/c1-8-5-10-14(11(23)6-8)18(26)15-9(16(10)24)3-2-4-12(15)29-21-20(28)19(27)17(25)13(7-22)30-21/h2-6,13,17,19-23,25,27-28H,7H2,1H3/t13-,17-,19+,20-,21-/m1/s1 |
| InChIKey | WMMOMSNMMDMSRB-JNHRPPPUSA-N |
| Formula | C21H20O9 |
| HBA | 9 |
| HBD | 5 |
| MW | 416.38 |
| Rotatable Bonds | 3 |
| TPSA | 153.75 |
| LogP | -0.35 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.33 |
| Exact Mass | 416.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Asphodelus microcarpus | Liliaceae | Plantae | 49697 |
Showing of synonyms
Chrysophanol-8-mono-beta-D-glucoside
13241-28-6
Chrysophanol 8-O-glucoside
Pulmatin
1-hydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
5D9G301STW
9,10-Anthracenedione, 8-(beta-D-glucopyranosyloxy)-1-hydroxy-3-methyl-
Chrysophanol-8-O-glucoside
Chrysophanol-8-beta-D-glucoside
DTXSID60157529
Chrysophanol 8-O-beta-D-glucopyranoside
CHRYSOPHANOL-8-.BETA.-D-GLUCOSIDE
CHRYSOPHANOL-8-O-.BETA.-D-GLUCOSIDE
O-.BETA.-D-GLUCOPYRANOSYLCHRYSOPHANOL
CHRYSOPHANOL-8-MONO-.BETA.-D-GLUCOSIDE
CHRYSOPHANOL 8-O-.BETA.-D-GLUCOPYRANOSIDE
ANTHRAQUINONE, 8-(.BETA.-D-GLUCOPYRANOSYLOXY)-1-HYDROXY-3-METHYL-
9,10-ANTHRACENEDIONE, 8-(.BETA.-D-GLUCOPYRANOSYLOXY)-1-HYDROXY-3-METHYL-
1-hydroxy-3-methyl-8-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyanthracene-9,10-dione
CP-8-O-glc
DTXCID6080020
Chrysophanol-8-O-beta-D-glucoside
O-BETA-D-GLUCOPYRANOSYLCHRYSOPHANOL
ANTHRAQUINONE, 8-(BETA-D-GLUCOPYRANOSYLOXY)-1-HYDROXY-3-METHYL-
Chrysophanol 8-glucoside
Chrysophanol 8-O-beta-D-glucoside
Chrysophanol-8-O-|A-D-glucopyranoside
CHEBI:3688
Chrysophanol-8-glucoside
UNII-5D9G301STW
MFCD20260508
Chrysophanol-8-O-beta-D-glucopyranoside
Chrysophanol8-O-glucoside
CHEMBL443804
SCHEMBL25257975
HY-N2395R
HY-N2395
NAA24128
LMPK13040007
AKOS032948547
Chrysophanol 8-O-glucoside (Standard)
8-hydroxy-6-methyl-9,10-dioxo-9,10-dihydroanthracen-1-yl beta-D-glucopyranoside
DA-51886
MS-27238
CS-0022597
NS00094742
F17668
Q27106165
GLUCOPYRANOSIDE, 8-HYDROXY-6-METHYL-1-ANTHRAQUINONYL
8-(beta-D-glucopyranosyloxy)-1-hydroxy-3-methyl-9,10-anthraquinone
9,10-Anthracenedione, 8-(|A-D-glucopyranosyloxy)-1-hydroxy-3-methyl-
GLUCOPYRANOSIDE, 8-HYDROXY-6-METHYL-1-ANTHRAQUINONYL, .BETA.-D-
1-Hydroxy-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-hydroxy-3-methyl-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
9,10-Anthracenedione, 8-(ss-D-glucopyranosyloxy)-1-hydroxy-3-methyl- (9CI, ACI)
8-(ss-D-Glucopyranosyloxy)-1-hydroxy-3-methyl-9,10-anthracenedione (ACI)
Anthraquinone, 8-(ss-D-glucopyranosyloxy)-1-hydroxy-3-methyl- (8CI)
Glucopyranoside, 8-hydroxy-6-methy
- Rizk A, Hammouda F, et al. (1972). Anthraquinones of Asphodelus microcarpus. Phytochemistry, 1972, 11(6), 2122-2125. [View]
Pubchem:
442731
Cas:
13241-28-6
Gnps:
CCMSLIB00006425456
Zinc:
ZINC000004098657
Kegg Ligand:
C10316
Chebi:
3688
Nmrshiftdb2:
60031449
Chembl:
CHEMBL443804
Comptox:
DTXSID60157529
CPRiL:
78628
SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3OC4CCCCO4
Level: 1
Mol. Weight: 416.38 g/mol
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 416.38 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 416.38 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.61
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.060
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.33
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.950
- Plasma Protein Binding
- 86.51
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.160
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.550
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.730
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.800
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -27.980
- Rat (Acute)
- 2.870
- Rat (Chronic Oral)
- 4.000
- Fathead Minnow
- 4.160
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 537.360
- Hydration Free Energy
- -8.880
- Log(D) at pH=7.4
- 0.770
- Log(P)
- 1.02
- Log S
- -3.19
- Log(Vapor Pressure)
- -11.74
- Melting Point
- 183.23
- pKa Acid
- 4.73
- pKa Basic
- 5.22
| 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 | 0.9729 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9137 |
| E3 ubiquitin-protein ligase Mdm2 | P56273 | MDM2_XENLA | Xenopus laevis | 3 | 0.8754 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8740 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8621 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8563 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8319 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.8310 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8150 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8090 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7963 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7959 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.7945 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7853 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7776 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7747 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7743 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7655 |
| Prostaglandin E synthase 2 | Q9N0A4 | PGES2_MACFA | Macaca fascicularis | 3 | 0.7506 |
| Beta sliding clamp | P0A988 | DPO3B_ECOLI | Escherichia coli | 3 | 0.7486 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7479 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 2 | 0.7466 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7386 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 2 | 0.7376 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7373 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7370 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7363 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7321 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7314 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7310 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7287 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7275 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7240 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7157 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7138 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7132 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7126 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 3 | 0.7121 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7119 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7117 |
| 6-phosphogluconate dehydrogenase, decarboxylating | P96789 | 6PGD_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7090 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7080 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7052 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7032 |