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Quercetin 3-acetyl-O-rhamnoside

Family: Moraceae
Kingdom: Plantae
Class: Flavonoid

Canonical Smiles	CC(=O)O[C@H]1[C@@H](O[C@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)C)Oc1c(oc2c(c1=O)c(O)cc(c2)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C27H26O14/c1-10-22(37-11(2)28)25(38-12(3)29)26(39-13(4)30)27(36-10)41-24-21(35)20-18(34)8-15(31)9-19(20)40-23(24)14-5-6-16(32)17(33)7-14/h5-10,22,25-27,31-34H,1-4H3/t10-,22-,25+,26+,27-/m0/s1
InChIKey	QTVHEWFZECLXHX-AQSARAKTSA-N
Formula	C₂₇H₂₆O₁₄
HBA	14
HBD	4
MW	574.49
Rotatable Bonds	6
TPSA	208.49
LogP	2.2
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	574.13
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ficus sur	Moraceae	Plantae	100575

Showing of synonyms

Greenham JR, Grayer RJ, et al. (2007). Intra-and interspecific variations in vacuolar flavonoids among Ficus species from the Budongo Forest, Uganda.. Biochemical systematics and ecology,2007,35(2),81-90. [View] [PubMed]

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 322.36 g/mol

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

Level: 1

Mol. Weight: 246.26 g/mol

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

Level: 1

Mol. Weight: 222.24 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.32
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.68
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 1.37

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.94
Plasma Protein Binding: 83.07
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: 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: 14.33
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.05
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.15
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.55
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -3262.68
Rat (Acute): 2.47
Rat (Chronic Oral): 2.74
Fathead Minnow: 15.28
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 546.88
Hydration Free Energy: -2.96
Log(D) at pH=7.4: 1.9
Log(P): 3.05
Log S: -4.29
Log(Vapor Pressure): -9.04
Melting Point: 219.12
pKa Acid: 7.61
pKa Basic: 0.7

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9770
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9770
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.9270
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.9270
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8981
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8981
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8970
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8970
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8923
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8923
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8901
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8901
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8829
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8829
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8676
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8676
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8606
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8606
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8561
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8561
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8489
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8489
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8482
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8482
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8477
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8477
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8461
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8461
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8373
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8373
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8202
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8202
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8196
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8196
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8180
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8180
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8159
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8159
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7931
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7931
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7924
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7924
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7900
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7900
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7898
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7898
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7864
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7864
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7854
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7854
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7846
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7846
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7778
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7778
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7756
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7756
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7718
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7718
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7714
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7714
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7681
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7681
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	4	0.7646
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	4	0.7646
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7639
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7639
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7601
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7601
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7575
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7575
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7530
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7530
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7520
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7520
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7482
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7482
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7476
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7476
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7468
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7468
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	7	0.7467
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	7	0.7467
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7458
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7458
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7457
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7457
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7448
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7448
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7421
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7421
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7378
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7378
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7376
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7376
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7350
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7350
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7307
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7307
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7303
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7303
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7239
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7239
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7196
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7196
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7187
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7187
Beta-secretase 2	Q9Y5Z0	BACE2_HUMAN	Homo sapiens	2	0.7181
Beta-secretase 2	Q9Y5Z0	BACE2_HUMAN	Homo sapiens	2	0.7181
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7146
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7146
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7099
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7099
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7076
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7076
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7074
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7074
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7069
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7069
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7036
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7036
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7010
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7010
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7003
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7003
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7002
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7002

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