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Methoxyquercetin-O-glucoside

Family: Plantae - Tamaricaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	OC[C@H]1OC(Oc2cc(O)cc3c2c(=O)c(c(o3)c2ccc(c(c2)O)O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C22H22O12/c1-31-21-17(28)15-12(32-20(21)8-2-3-10(25)11(26)4-8)5-9(24)6-13(15)33-22-19(30)18(29)16(27)14(7-23)34-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3/t14-,16-,18+,19-,22?/m1/s1
InChIKey	WAJZHIMAJHLZQB-YOICORKUSA-N
Formula	C₂₂H₂₂O₁₂
HBA	12
HBD	7
MW	478.41
Rotatable Bonds	5
TPSA	199.51
LogP	-0.24
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	Tamarix articulata	Tamaricaceae	Plantae	189786

Showing of synonyms

Shaalan Y.M, Handoussa H, et al. (2018). Destabilizing the interplay between miR-1275 and IGF2BPs by Tamarix articulata and quercetin in hepatocellular carcinoma. Nat Prod Res,2018,32(18),2217-2220. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)cccc3OC4CCCCO4

Level: 2

Mol. Weight: 478.41 g/mol

SMILES: O=c1ccoc(c12)cccc2OC3CCCCO3

Level: 1

Mol. Weight: 478.41 g/mol

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

Level: 1

Mol. Weight: 478.41 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 478.41 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.71
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.42
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.8

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.84
Plasma Protein Binding: 74.38
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: 14.43
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.55
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.95
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.51
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: -185.26
Rat (Acute): 2.32
Rat (Chronic Oral): 4.1
Fathead Minnow: 4.17
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: 627.13
Hydration Free Energy: -3.74
Log(D) at pH=7.4: 0.22
Log(P): -0.16
Log S: -4.32
Log(Vapor Pressure): -12.07
Melting Point: 214.11
pKa Acid: 5.33
pKa Basic: 6.16

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9674
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9508
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9240
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9100
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9014
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8980
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8914
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8891
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8792
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8706
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8583
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8574
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.8367
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8314
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8286
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8277
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8203
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8199
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8183
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.8174
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8145
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8134
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8114
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8106
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8083
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8056
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8039
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8016
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8012
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8011
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7776
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7776
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7737
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.7720
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7688
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7683
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.7678
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7676
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7663
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7613
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7609
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7606
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7594
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7590
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7551
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7506
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7498
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7479
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7464
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7376
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7373
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7364
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7356
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7352
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7336
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7324
NTPase P4	Q94M05	Q94M05_9VIRU	Pseudomonas phage phi12	3	0.7269
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7262
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7261
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7246
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7241
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7238
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7237
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7215
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7199
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7199
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7187
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7175
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7164
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7160
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7158
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7155
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.7144
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7129
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7128
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7113
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7111
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7105
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7085
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7070
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7063
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7061
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7060
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7052
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7043
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7028
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7027
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7021
Aspartokinase 1, chloroplastic	Q9LYU8	AK1_ARATH	Arabidopsis thaliana	3	0.7020
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7015
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7010
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7009
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7003

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