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3-O-(2′′-O-galloyl-alpha-L-rhamnopyranosyl) quercetin
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonol Glycoside
| Canonical Smiles | Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1OC(=O)c1cc(O)c(c(c1)O)O)O)O)c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C28H24O15/c1-9-20(35)23(38)26(42-27(39)11-5-16(33)21(36)17(34)6-11)28(40-9)43-25-22(37)19-15(32)7-12(29)8-18(19)41-24(25)10-2-3-13(30)14(31)4-10/h2-9,20,23,26,28-36,38H,1H3/t9-,20-,23+,26+,28-/m0/s1 |
| InChIKey | KTTNFIOZYNBKEY-YIOJSCHVSA-N |
| Formula | C28H24O15 |
| HBA | 15 |
| HBD | 9 |
| MW | 600.49 |
| Rotatable Bonds | 5 |
| TPSA | 257.04 |
| LogP | 1.47 |
| Number Rings | 5 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 43 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.21 |
| Exact Mass | 600.11 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Euphorbia gaditana | Euphorbiaceae | Plantae | 3990 |
Showing of synonyms
3-O-(2′′-O-galloyl-alpha-L-rhamnopyranosyl) quercetin
2''-O-Galloylquercitrin
80229-08-9
[(2S,3R,4R,5R,6S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl] 3,4,5-trihydroxybenzoate
CHEMBL3236511
MEGxp0_001105
SCHEMBL15773514
ACon1_001050
DTXSID701345785
HY-N8844
BDBM50004201
AKOS040761014
FS-8172
DA-69821
CS-0149162
(2S,3R,4R,5R,6S)-2-((2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl 3,4,5-trihydroxybenzoate
(2S,3R,4R,5R,6S)-2-{[2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4-OXOCHROMEN-3-YL]OXY}-4,5-DIHYDROXY-6-METHYLOXAN-3-YL 3,4,5-TRIHYDROXYBENZOATE
- Badaoui M, Magid A, et al. (2020). Antioxidant activity-guided isolation of constituents from Euphorbia gaditana Coss. and their antioxidant and tyrosinase inhibitory activities. Phytochemistry Letters, 2020, 39, 99-104. [View]
Pubchem:
10031482
Cas:
80229-08-9
Gnps:
CCMSLIB00004706294
Zinc:
ZINC000033861406
Nmrshiftdb2:
60029144
Chembl:
CHEMBL3236511
Bindingdb:
50004201
No compound-protein relationship available.
SMILES: c1ccccc1C(=O)OC2C(OCCC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5
Level: 3
Mol. Weight: 600.49 g/mol
SMILES: c1ccccc1C(=O)OC2C(OCCC2)Oc(c3=O)coc(c34)cccc4
Level: 2
Mol. Weight: 600.49 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 600.49 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 600.49 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 600.49 g/mol
SMILES: c1ccccc1C(=O)OC2CCCOC2
Level: 1
Mol. Weight: 600.49 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 600.49 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 600.49 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 600.49 g/mol
Antioxidant
Absorption
- Caco-2 (logPapp)
- -6.81
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.4
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 8.4
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.86
- Plasma Protein Binding
- 75.03
- 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
- 14.19
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.48
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.31
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.51
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- -12619.75
- Rat (Acute)
- 2.45
- Rat (Chronic Oral)
- 4.3
- Fathead Minnow
- 29.69
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 533.25
- Hydration Free Energy
- -3.17
- Log(D) at pH=7.4
- 1.04
- Log(P)
- 2.1
- Log S
- -5.77
- Log(Vapor Pressure)
- -13.82
- Melting Point
- 240.06
- pKa Acid
- 4.88
- pKa Basic
- 6.4
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9752 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9254 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8937 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8829 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 4 | 0.8788 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8705 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8684 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8642 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8510 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 4 | 0.8435 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8338 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8284 |
| Antitumor antibiotic C-1027 apoprotein | Q06110 | CAGA_STRGL | Streptomyces globisporus | 3 | 0.8263 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8230 |
| Botulinum neurotoxin type A | P0DPI0 | BXA1_CLOBO | Clostridium botulinum | 3 | 0.8159 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8063 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.8043 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7923 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.7908 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.7864 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.7862 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7839 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7815 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7751 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7735 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7695 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.7634 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7607 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7598 |
| Caspase-6 | P55212 | CASP6_HUMAN | Homo sapiens | 3 | 0.7564 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7479 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7474 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7438 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7377 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7344 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7327 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7291 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7232 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7215 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7205 |
| Beta-glucuronidase | P05804 | BGLR_ECOLI | Escherichia coli | 3 | 0.7193 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7191 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7188 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.7187 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 4 | 0.7186 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7170 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7152 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7137 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7124 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7123 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7092 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 4 | 0.7065 |
| Serine/threonine-protein kinase RAD53 | P22216 | RAD53_YEAST | Saccharomyces cerevisiae | 4 | 0.7061 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7055 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7027 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7013 |