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Kaempferol 3-O-beta-D-glucopyranoside-7-O-alpha-L-rhamnoside
- Family: Plantae - Resedaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonol Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(38-9)39-12-6-13(30)16-14(7-12)40-24(10-2-4-11(29)5-3-10)25(19(16)33)42-27-23(37)21(35)18(32)15(8-28)41-27/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26-,27-/m0/s1 |
| InChIKey | JYXSWDCPHRTYGU-RVCYDTIBSA-N |
| Formula | C27H30O15 |
| HBA | 15 |
| HBD | 9 |
| MW | 594.52 |
| Rotatable Bonds | 6 |
| TPSA | 249.2 |
| LogP | -1.74 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 42 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.44 |
| Exact Mass | 594.16 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Farsetia aegyptia | Alysseae | Plantae | 359842 |
| 2 | Ochradenus baccatus | Resedaceae | Plantae | 264972 |
Showing of synonyms
Kaempferol 3-O-beta-D-glucopyranoside-7-O-alpha-L-rhamnoside
CHEMBL1929193
CHEBI:68882
Kaempferol 3-O-beta-D-glucopyranosyl-7-O-alpha-L-rhamnopyranoside
4H-1-Benzopyran-4-one, 7-[(6-deoxy-|A-L-mannopyranosyl)oxy]-3-(|A-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-
5-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
4H-1-Benzopyran-4-one, 7-[(6-deoxy-
Kaempferol 3-glucoside 7-rhamnoside
A-L-mannopyranosyl)oxy]-3-(
SCHEMBL9993267
DTXSID90946741
BDBM50359314
AKOS030553662
Kaempferol 3-O-glucoside 7-O-rhamnoside
XK161849
NS00097623
Q27137238
Kaempferol 3-O-beta-glucopyranoside-7-O-alpha-rhamnopyranoside
Kaempferol-3-O-beta-D-glucopyranoside-7-O-alpha-L-rhamnopyranoside
4H-1-Benzopyran-4-one, 7-[(6-deoxy--L-mannopyranosyl)oxy]-3-(-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-
4H-1-Benzopyran-4-one, 7-[(6-deoxy-I+/--L-mannopyranosyl)oxy]-3-(I(2)-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-
7-[(6-Deoxy-a-L-mannopyranosyl)oxy]-3-(B-D-glucopyranosyloxy)-5-hydroxy- 2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Kaempferol 3-O-B-D -glucopyranoside 7-O-a-L-rhamnopyranoside
7-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl beta-D-glucopyranoside
- Marzouk M.M, Al-Nowaihi A.S.M, et al. (2010). Chemosystematic studies on certain species of the family Brassicaceae(Cruciferae) in Egypt. Biochemical Systematics and Ecology, 2010, 38(4), 680–685.. [View]
- Berrehal D, Khalfallah A, et al. (2012). Flavononol glycosides of Reseda arabica (Resedaceae). Records of Natural Products,2012,6(4),68-370.. [View]
Pubchem:
21606527
Gnps:
CCMSLIB00004687824
Zinc:
ZINC000067902860
Chebi:
68882
Nmrshiftdb2:
60022462
Metabolights:
MTBLC68882
Chembl:
CHEMBL1929193
Bindingdb:
50359314
No compound-protein relationship available.
SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC5CCCCO5
Level: 3
Mol. Weight: 594.52 g/mol
SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC4CCCCO4
Level: 2
Mol. Weight: 594.52 g/mol
SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4
Level: 2
Mol. Weight: 594.52 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 594.52 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 594.52 g/mol
SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3
Level: 1
Mol. Weight: 594.52 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 594.52 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 594.52 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 594.52 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 594.52 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.55
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.320
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 6.68
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.870
- Plasma Protein Binding
- 77.4
- 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
- 7.150
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -3.660
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.030
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.340
- 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
- -9482.390
- Rat (Acute)
- 2.310
- Rat (Chronic Oral)
- 4.380
- Fathead Minnow
- 20.730
- 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
- 500.290
- Hydration Free Energy
- -2.990
- Log(D) at pH=7.4
- -0.350
- Log(P)
- -0.62
- Log S
- -4.42
- Log(Vapor Pressure)
- -12.76
- Melting Point
- 223.93
- pKa Acid
- 3.69
- pKa Basic
- 5.95
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9526 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9142 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8856 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8592 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8387 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8289 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8112 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8077 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7969 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7864 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.7778 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7735 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7719 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7717 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7611 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7595 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7564 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7550 |
| Periplasmic pH-dependent serine endoprotease DegQ | P39099 | DEGQ_ECOLI | Escherichia coli | 4 | 0.7535 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7514 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7473 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7456 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7433 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7404 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7294 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7254 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 3 | 0.7233 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7211 |
| Tannase | B3Y018 | B3Y018_LACPN | Lactiplantibacillus plantarum | 4 | 0.7145 |
| Beta-glucuronidase | P05804 | BGLR_ECOLI | Escherichia coli | 3 | 0.7103 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 4 | 0.7102 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 4 | 0.7075 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7065 |
| 16S rRNA (guanine(1405)-N(7))-methyltransferase | Q763K9 | Q763K9_ECOLX | Escherichia coli | 3 | 0.7064 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.7049 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7005 |