Myricetin 3-O-(6′′-O-methyl-beta-D-glucuronopyranoside) - Compound Card

Myricetin 3-O-(6′′-O-methyl-beta-D-glucuronopyranoside)

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Myricetin 3-O-(6′′-O-methyl-beta-D-glucuronopyranoside)

Structure
Zoomed Structure
  • Family: Plantae - Myrtaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles COC(=O)[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2cc(O)c(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C22H20O14/c1-33-21(32)20-16(30)15(29)17(31)22(36-20)35-19-14(28)12-8(24)4-7(23)5-11(12)34-18(19)6-2-9(25)13(27)10(26)3-6/h2-5,15-17,20,22-27,29-31H,1H3/t15-,16-,17+,20-,22+/m0/s1
InChIKey QTFNUOCIFLDZKZ-NTKSAMNMSA-N
Formula C22H20O14
HBA 14
HBD 8
MW 508.39
Rotatable Bonds 4
TPSA 236.81
LogP -0.65
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 508.09
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia gaditana Euphorbiaceae Plantae 3990
2 Eugenia jambolana Myrtaceae Plantae 260142

Showing of synonyms

  • Mahmoud I.I, Marzouk M.S, et al. (2001). Acylated flavonol glycosides from Eugenia jambolana leaves. Phytochemistry, 2001, 58(8), 1239-44. [View] [PubMed]
  • 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: 15293407

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 508.39 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 508.39 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 508.39 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 508.39 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 508.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 508.39 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-6.59
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.730
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.770
Plasma Protein Binding
68.79
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
14.910
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.540
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.150
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.550
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
-386.310
Rat (Acute)
2.300
Rat (Chronic Oral)
4.310
Fathead Minnow
3.640
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
678.230
Hydration Free Energy
-3.820
Log(D) at pH=7.4
-0.020
Log(P)
0.32
Log S
-4.45
Log(Vapor Pressure)
-11.94
Melting Point
190.22
pKa Acid
4.62
pKa Basic
7.95
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9252
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8920
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8859
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8670
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8451
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8395
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8315
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8248
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8080
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8024
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7908
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7901
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7836
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7759
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7757
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7747
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7735
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7720
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7712
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7706
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7443
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7377
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7341
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7267
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7092
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7076
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7052
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7047
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7034

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