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3-O-(3′′-O-galloyl-alpha-L-rhamnopyranosyl) quercetin

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]1O)OC(=O)c1cc(O)c(c(c1)O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C28H24O15/c1-9-20(35)25(42-27(39)11-5-16(33)21(36)17(34)6-11)23(38)28(40-9)43-26-22(37)19-15(32)7-12(29)8-18(19)41-24(26)10-2-3-13(30)14(31)4-10/h2-9,20,23,25,28-36,38H,1H3/t9-,20-,23+,25+,28-/m0/s1
InChIKey	JFLAOPHOUGDFGC-ILADGKKJSA-N
Formula	C₂₈H₂₄O₁₅
HBA	15
HBD	9
MW	600.49
Rotatable Bonds	5
TPSA	257.04
LogP	1.47
Number Rings	5
Number Aromatic Rings	4
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.21
Exact Mass	600.11
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Euphorbia gaditana	Euphorbiaceae	Plantae	3990

Showing of synonyms

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: 23786426

Cas: 503446-90-0

Gnps: CCMSLIB00004706513

Zinc: ZINC000033861410

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC2CC(OCC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 600.49 g/mol

SMILES: c1ccccc1C(=O)OC2CC(OCC2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 600.49 g/mol

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

Level: 2

Mol. Weight: 600.49 g/mol

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

Level: 1

Mol. Weight: 600.49 g/mol

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

Level: 1

Mol. Weight: 600.49 g/mol

SMILES: c1ccccc1C(=O)OC2CCOCC2

Level: 1

Mol. Weight: 600.49 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 600.49 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 600.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 600.49 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -6.75
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.46
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 8.29

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.86
Plasma Protein Binding: 76.3
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: 14.3
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.06
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.26
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.48
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: -12617.52
Rat (Acute): 2.5
Rat (Chronic Oral): 4.24
Fathead Minnow: 29.55
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 528.53
Hydration Free Energy: -3.17
Log(D) at pH=7.4: 1.05
Log(P): 2.11
Log S: -5.68
Log(Vapor Pressure): -13.67
Melting Point: 250.26
pKa Acid: 5.04
pKa Basic: 6.02

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9766
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9298
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9095
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9021
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8961
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8945
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8928
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8888
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8872
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8734
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8712
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8684
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8535
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8525
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8517
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8482
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8441
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8400
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8365
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8364
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8259
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8255
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8215
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8214
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8193
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8140
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8124
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8118
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8091
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8041
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8035
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8031
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8017
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	7	0.8007
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7987
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7968
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7936
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.7923
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7878
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7877
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7871
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7849
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7836
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7819
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7798
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7787
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7769
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7769
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7759
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7705
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	5	0.7641
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7638
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7635
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7581
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7556
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7553
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7536
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7501
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7475
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.7467
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7459
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7443
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7436
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7429
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7401
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7374
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7364
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7355
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	4	0.7353
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7351
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7328
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7318
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7307
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7306
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7290
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7270
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7269
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7265
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7251
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7222
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7190
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7177
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7171
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7166
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7165
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7146
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7143
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7141
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7124
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7115
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7110
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7084
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7082
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7062
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7043
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7041
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7036
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7029
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7017
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7014
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7009

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