Myricetin 4'-methyl ether 3-O-alpha-L-rhamnopyranoside - Compound Card

Myricetin 4'-methyl ether 3-O-alpha-L-rhamnopyranoside

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Myricetin 4'-methyl ether 3-O-alpha-L-rhamnopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Myrtaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles COc1c(O)cc(cc1O)c1oc2cc(O)cc(c2c(=O)c1O[C@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O)O
InChI InChI=1S/C22H22O12/c1-7-15(27)17(29)18(30)22(32-7)34-21-16(28)14-10(24)5-9(23)6-13(14)33-19(21)8-3-11(25)20(31-2)12(26)4-8/h3-7,15,17-18,22-27,29-30H,1-2H3/t7-,15-,17+,18+,22-/m1/s1
InChIKey NAQNISJXKDSYJD-BJSHTXHQSA-N
Formula C22H22O12
HBA 12
HBD 7
MW 478.41
Rotatable Bonds 4
TPSA 199.51
LogP 0.5
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 478.11
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Eugenia jambolana Myrtaceae Plantae 260142
2 Syzygium grande Myrtaceae Plantae 1042139

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]
  • Samy M.N, Sugimoto S, et al. (2014). One new flavonoid xyloside and one new natural triterpene rhamnoside from the leaves of Syzygium grande. Phytochemistry Letters, 2014, 10, 86-90. [View]
Pubchem: 162950269

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 478.41 g/mol

Structure

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

Level: 1

Mol. Weight: 478.41 g/mol

Structure

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

Level: 1

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 478.41 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.81
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.650
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.820
Plasma Protein Binding
76.56
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
15.140
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.210
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.000
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.120
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
-153.930
Rat (Acute)
2.350
Rat (Chronic Oral)
4.160
Fathead Minnow
3.840
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
634.390
Hydration Free Energy
-3.740
Log(D) at pH=7.4
0.920
Log(P)
0.75
Log S
-4.86
Log(Vapor Pressure)
-10.71
Melting Point
200.98
pKa Acid
5.38
pKa Basic
5.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.9015
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8982
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8930
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8833
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8773
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8737
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8699
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8584
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8580
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8514
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8277
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8019
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.7860
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7791
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7710
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7589
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7582
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7522
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7521
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7468
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7430
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7417
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7413
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7377
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7356
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7337
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7297
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7274
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7257
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7255
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7253
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7222
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7209
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7116
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7075
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7047
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7044
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7041
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7003

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