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3-O-(2′′-O-galloyl-alpha-L-rhamnopyranosyl) myricetin
- 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)c1cc(O)c(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C28H24O16/c1-8-19(35)23(39)26(43-27(40)10-4-15(33)21(37)16(34)5-10)28(41-8)44-25-22(38)18-12(30)6-11(29)7-17(18)42-24(25)9-2-13(31)20(36)14(32)3-9/h2-8,19,23,26,28-37,39H,1H3/t8-,19-,23+,26+,28-/m0/s1 |
| InChIKey | IXDHJNNHLVGCLC-MXXRNXGISA-N |
| Formula | C28H24O16 |
| HBA | 16 |
| HBD | 10 |
| MW | 616.48 |
| Rotatable Bonds | 5 |
| TPSA | 277.27 |
| LogP | 1.18 |
| Number Rings | 5 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 44 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.21 |
| Exact Mass | 616.11 |
| 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) myricetin
56939-52-7
Gallomyricitrin
2''-O-Galloylmyricitrin
[(2S,3R,4R,5R,6S)-2-[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl] 3,4,5-trihydroxybenzoate
Desmanthin-1
SCHEMBL2963374
CHEMBL2152656
AKOS040761013
FS-8176
CS-0149384
NS00097489
(2S,3R,4R,5R,6S)-2-{[5,7-DIHYDROXY-4-OXO-2-(3,4,5-TRIHYDROXYPHENYL)CHROMEN-3-YL]OXY}-4,5-DIHYDROXY-6-METHYLOXAN-3-YL 3,4,5-TRIHYDROXYBENZOATE
NCGC00385142-01![(2S,3R,4R,5R,6S)-2-[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-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:
5316590
Cas:
56939-52-7
Gnps:
CCMSLIB00000848954
Zinc:
ZINC000070454922
Nmrshiftdb2:
60029111
Chembl:
CHEMBL2152656
CPRiL:
432429
SMILES: c1ccccc1C(=O)OC2C(OCCC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5
Level: 3
Mol. Weight: 616.48 g/mol
SMILES: c1ccccc1C(=O)OC2C(OCCC2)Oc(c3=O)coc(c34)cccc4
Level: 2
Mol. Weight: 616.48 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 616.48 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 616.48 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 616.48 g/mol
SMILES: c1ccccc1C(=O)OC2CCCOC2
Level: 1
Mol. Weight: 616.48 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 616.48 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 616.48 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 616.48 g/mol
Antioxidant
Absorption
- Caco-2 (logPapp)
- -6.73
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.54
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 12.16
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.74
- Plasma Protein Binding
- 66.96
- 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
- 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
- 14.17
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.27
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.24
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.54
- 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
- -18433.82
- Rat (Acute)
- 2.45
- Rat (Chronic Oral)
- 4.51
- Fathead Minnow
- 41.63
- 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
- 515.06
- Hydration Free Energy
- -3.17
- Log(D) at pH=7.4
- 0.49
- Log(P)
- 1.65
- Log S
- -5.7
- Log(Vapor Pressure)
- -15.93
- Melting Point
- 240.39
- pKa Acid
- 4.65
- pKa Basic
- 7.92
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9263 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9067 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8979 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 4 | 0.8878 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8739 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8663 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8567 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8536 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 4 | 0.8442 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8407 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8367 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8227 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8189 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.8145 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8056 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8000 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7983 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7954 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7918 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7903 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7815 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7790 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7773 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7726 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7683 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7626 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7563 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 4 | 0.7503 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7449 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7375 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7375 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7360 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7294 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.7292 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7268 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7266 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7236 |
| Glucose-1-phosphate thymidylyltransferase | Q9AGY4 | Q9AGY4_ANETH | Aneurinibacillus thermoaerophilus | 5 | 0.7234 |
| Serine/threonine-protein kinase RAD53 | P22216 | RAD53_YEAST | Saccharomyces cerevisiae | 4 | 0.7222 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.7210 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | P49354 | FNTA_HUMAN | Homo sapiens | 3 | 0.7197 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7185 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7180 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7159 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7153 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.7133 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7118 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7107 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7103 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7096 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7089 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7083 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7050 |
| Small heat shock protein StHsp14.0 | Q970D9 | Q970D9_SULTO | Sulfurisphaera tokodaii | 3 | 0.7027 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7015 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7012 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7011 |