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Quercetin 3-O-[(2,4-diacetyl-alpha-rhamnopyranosyl)-(1→6)]-3,4-diacetyl-beta-galactopyranoside

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

Canonical Smiles	CC(=O)OC1[C@H](OC(=O)C)C(COC2O[C@@H](C)C([C@@H]([C@H]2OC(=O)C)O)OC(=O)C)O[C@H]([C@H]1O)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C35H38O20/c1-12-28(49-13(2)36)26(45)33(52-16(5)39)35(48-12)47-11-23-30(50-14(3)37)32(51-15(4)38)27(46)34(54-23)55-31-25(44)24-21(43)9-18(40)10-22(24)53-29(31)17-6-7-19(41)20(42)8-17/h6-10,12,23,26-28,30,32-35,40-43,45-46H,11H2,1-5H3/t12-,23?,26-,27-,28?,30+,32?,33+,34-,35?/m0/s1
InChIKey	FSJGQFHHFGJQNB-KLRBSOGOSA-N
Formula	C₃₅H₃₈O₂₀
HBA	20
HBD	6
MW	778.67
Rotatable Bonds	10
TPSA	293.71
LogP	0.6
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	55
Formal Charge	0
Fraction CSP3	0.46
Exact Mass	778.2
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Capsicum annum	Solanaceae	Plantae	4072

Showing of synonyms

Allam A.E. (2021). Suppression of cytokine production by newly isolated flavonoids from pepper. Fitoterapia, 2021, 151, 104903. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 778.67 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 778.67 g/mol

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

Level: 2

Mol. Weight: 778.67 g/mol

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

Level: 1

Mol. Weight: 778.67 g/mol

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

Level: 1

Mol. Weight: 778.67 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 778.67 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 778.67 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 778.67 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 778.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.38
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 4.62
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 1350.44

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.77
Plasma Protein Binding: 57.67
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: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 14.48
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -32.79
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.96
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.49
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: -2452119.26
Rat (Acute): 2.45
Rat (Chronic Oral): 3.45
Fathead Minnow: 3102.22
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 268532.63
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 0.56
Log(P): 2.39
Log S: -4.44
Log(Vapor Pressure): -8855.7
Melting Point: 206.05
pKa Acid: -37.1
pKa Basic: -1.42

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9710
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9016
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8933
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8897
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8826
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8577
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8577
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8390
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8353
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8328
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8246
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8028
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8027
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7981
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7823
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7775
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7753
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7746
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7743
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7740
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7740
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7709
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7698
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7697
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7685
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7658
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.7646
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7616
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7610
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7609
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7555
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7498
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7495
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7492
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7467
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7405
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7373
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.7355
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7322
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7299
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7264
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7252
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7164
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7161
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7134
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7125
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7123
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7037
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7023
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7021
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7017
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7011
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7004

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