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Myricetin 3-O-glucuronide
- Family: Plantae - Onagraceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonoid Glycoside
| Canonical Smiles | Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@H](C(=O)O)[C@H](C(C1O)O)O)c1cc(O)c(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C21H18O14/c22-6-3-7(23)11-10(4-6)33-17(5-1-8(24)12(26)9(25)2-5)18(13(11)27)34-21-16(30)14(28)15(29)19(35-21)20(31)32/h1-4,14-16,19,21-26,28-30H,(H,31,32)/t14?,15-,16?,19-,21+/m0/s1 |
| InChIKey | MBWOCQLTCWTIJE-ROQVLGAUSA-N |
| Formula | C21H18O14 |
| HBA | 13 |
| HBD | 9 |
| MW | 494.36 |
| Rotatable Bonds | 4 |
| TPSA | 247.81 |
| LogP | -0.74 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.24 |
| Exact Mass | 494.07 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Epilobium hirsutum | Onagraceae | Plantae | 210355 |
Showing of synonyms
Myricetin 3-O-glucuronide
Myricetin 3-glucuronide
(2S,3S,6S)-6-[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
(2S,3S,4R,5R,6S)-6-((5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl)oxy)-3,4,5-trihydroxyoxane-2-carboxylate
(2S,3S,4R,5R,6S)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate
(2S,3S,6S)-6-(5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl)oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
77363-65-6
CHEBI:166633
LMPK12112437
- Barakat HH, Hussein SAM, et al. (1997). Polyphenolic metabolites of Epilobium hirsutum. Phytochemistry,1997,46(5),935-941. [View]
No compound-protein relationship available.
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 494.36 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 494.36 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 494.36 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 494.36 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 494.36 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 494.36 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.69
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -6.15
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 2.19
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.84
- Plasma Protein Binding
- 61.34
- 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
- 12.33
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -2.99
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.14
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.71
- 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
- -220.65
- Rat (Acute)
- 2.22
- Rat (Chronic Oral)
- 4.41
- Fathead Minnow
- 3.57
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 716.58
- Hydration Free Energy
- -4.14
- Log(D) at pH=7.4
- -2.15
- Log(P)
- 0.34
- Log S
- -3.68
- Log(Vapor Pressure)
- -12.89
- Melting Point
- 205.16
- pKa Acid
- 3.19
- pKa Basic
- 9.5
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9153 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9153 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 4 | 0.8831 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 4 | 0.8831 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8799 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8799 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8748 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8748 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8601 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8601 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8369 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8369 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8368 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8368 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8214 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8214 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.8172 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 4 | 0.8172 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8022 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.8022 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7756 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7756 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7745 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7745 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 4 | 0.7739 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 4 | 0.7739 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7711 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7711 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7687 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7687 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7680 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7680 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 3 | 0.7582 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 3 | 0.7582 |
| ADP-ribosyl-[dinitrogen reductase] hydrolase | A7XNI2 | A7XNI2_AZOBR | Azospirillum brasilense | 3 | 0.7528 |
| ADP-ribosyl-[dinitrogen reductase] hydrolase | A7XNI2 | A7XNI2_AZOBR | Azospirillum brasilense | 3 | 0.7528 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7437 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7437 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7419 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7419 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.7395 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.7395 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7379 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 3 | 0.7379 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7190 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7190 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7143 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7143 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7135 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7135 |
| Beta-hexosaminidase | Q9KU37 | NAGZ_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7081 |
| Beta-hexosaminidase | Q9KU37 | NAGZ_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7081 |