Select a section from the left sidebar
Emodin-6-O-alpha-L-rhamnoside
- Family: Plantae - Rhamnaceae
- Kingdom: Plantae
-
Class: Anthaquinone
- Subclass: Anthraquinone Glycoside
| Canonical Smiles | O[C@H]1[C@@H](O[C@H]([C@@H]([C@H]1O)O)C)Oc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)C |
|---|---|
| InChI | InChI=1S/C21H20O9/c1-7-3-10-14(12(22)4-7)18(26)15-11(17(10)25)5-9(6-13(15)23)30-21-20(28)19(27)16(24)8(2)29-21/h3-6,8,16,19-24,27-28H,1-2H3/t8-,16-,19+,20+,21-/m0/s1 |
| InChIKey | DTTVUKLWJFJOHO-FUCRAMRQSA-N |
| Formula | C21H20O9 |
| HBA | 9 |
| HBD | 5 |
| MW | 416.38 |
| Rotatable Bonds | 2 |
| TPSA | 153.75 |
| LogP | 0.39 |
| 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 | Rhamnus alaternus | Rhamnaceae | Plantae | 280017 |
Showing of synonyms
Emodin-6-O-alpha-L-rhamnoside
Frangulin A
521-62-0
EINECS 208-316-2
BRN 0059993
UNII-HXU301W02A
HXU301W02A
1,8-dihydroxy-3-methyl-6-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyanthracene-9,10-dione
FRANGULIN A [MI]
5-17-06-00267 (Beilstein Handbook Reference)
Anthraquinone, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1,8-dihydroxy-6-methyl-
3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-1,8-dihydroxy-6-methyl-9,10-anthracenedione
9,10-Anthracenedione, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-1,8-dihydroxy-6-methyl-
Frangulin A (8CI)
1,8-dihydroxy-3-methyl-6-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-anthracene-9,10-dione
EINECS 274-082-3
1,8-dihydroxy-3-methyl-6-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-anthracene-9,10-dione
1,8-dihydroxy-3-methyl-6-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyanthracene-9,10-dione
9,10-Anthracenedione, 3-((6-deoxy-L-mannopyranosyl)oxy)-1,8-dihydroxy-6-methyl-
208-316-2
CHEBI:5167
CHEMBL1172006
1,8-Dihydroxy-3-methyl-6-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)anthracene-9,10-dione
Frangulin A (Rhamnoxanthin)
SCHEMBL1426460
Frangulin A, analytical standard
DTXSID40966459
Emodin-L-rhamnoside
Rhamnoxanthin
HY-N8344
BDBM50333878
MFCD00016363
3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-1,8-dihydroxy-6-methylanthraquinone
AKOS040760401
FF65554
FS-10669
CS-0143373
NS00042806
A828950
Q27106673
4,5-Dihydroxy-7-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl 6-deoxyhexopyranoside
Pubchem:
196979
Cas:
521-62-0
Zinc:
ZINC000004098673
Kegg Ligand:
C10346
Chebi:
5167
Nmrshiftdb2:
60076502
Chembl:
CHEMBL1172006
Bindingdb:
50333878
No compound-protein relationship available.
SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)OC4CCCCO4
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)
- -6.87
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.13
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.32
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.88
- Plasma Protein Binding
- 86.11
- 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
- 12.18
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.35
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.72
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.09
- 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
- -21.94
- Rat (Acute)
- 2.54
- Rat (Chronic Oral)
- 3.9
- Fathead Minnow
- 4.23
- 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
- 532.65
- Hydration Free Energy
- -9.27
- Log(D) at pH=7.4
- 1.12
- Log(P)
- 2.42
- Log S
- -4.15
- Log(Vapor Pressure)
- -10.41
- Melting Point
- 207.39
- pKa Acid
- 5.34
- pKa Basic
- 4.54
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9296 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8939 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8921 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.8701 |
| E3 ubiquitin-protein ligase Mdm2 | P56273 | MDM2_XENLA | Xenopus laevis | 3 | 0.8682 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8584 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8582 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.8501 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8492 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8401 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8337 |
| Methionine aminopeptidase 2 | P50579 | MAP2_HUMAN | Homo sapiens | 3 | 0.8159 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8113 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8106 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.8086 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8086 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.8006 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7991 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7985 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7907 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7819 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7809 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7808 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7786 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7684 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7677 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7673 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7630 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7550 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7542 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 2 | 0.7415 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 4 | 0.7413 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7379 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 4 | 0.7377 |
| Acyl-homoserine-lactone synthase | Q4VSJ8 | Q4VSJ8_BURGL | Burkholderia glumae | 4 | 0.7344 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7324 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7319 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7316 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7307 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 4 | 0.7279 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7243 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7229 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7226 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7224 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7223 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7219 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7179 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7164 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7146 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7141 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7129 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 3 | 0.7127 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7114 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7070 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7054 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7034 |
| Fructose-1,6-bisphosphatase 1 | P00636 | F16P1_PIG | Sus scrofa | 3 | 0.7032 |
| Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.7031 |
| Enoyl-ACP reductase | Q9BJJ9 | Q9BJJ9_PLAFA | Plasmodium falciparum | 3 | 0.7024 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7021 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7017 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7016 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 4 | 0.7008 |