Quercetin 3-acetyl-O-glucoside - Compound Card

Quercetin 3-acetyl-O-glucoside

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Quercetin 3-acetyl-O-glucoside

Structure
Zoomed Structure
  • Family: Moraceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles CC(=O)OC[C@@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)O)O)[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
InChI InChI=1S/C29H28O16/c1-11(30)39-10-21-25(40-12(2)31)27(41-13(3)32)28(42-14(4)33)29(44-21)45-26-23(38)22-19(37)8-16(34)9-20(22)43-24(26)15-5-6-17(35)18(36)7-15/h5-9,21,25,27-29,34-37H,10H2,1-4H3/t21-,25-,27+,28+,29-/m0/s1
InChIKey GTDQGECQTNEMED-GIZSGOPNSA-N
Formula C29H28O16
HBA 16
HBD 4
MW 632.53
Rotatable Bonds 8
TPSA 234.79
LogP 1.74
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 45
Formal Charge 0
Fraction CSP3 0.34
Exact Mass 632.14
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ficus exasperata Moraceae Plantae 459060

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.

Structure

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

Level: 2

Mol. Weight: 322.36 g/mol

Structure

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

Level: 1

Mol. Weight: 246.26 g/mol

Structure

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

Level: 1

Mol. Weight: 222.24 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.31
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.74
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
10.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.83
Plasma Protein Binding
76.08
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.34
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.31
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.11
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.6
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
-20270.29
Rat (Acute)
2.46
Rat (Chronic Oral)
3.12
Fathead Minnow
47.4
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
400.65
Hydration Free Energy
-2.92
Log(D) at pH=7.4
1.65
Log(P)
2.77
Log S
-3.91
Log(Vapor Pressure)
-13.46
Melting Point
215.84
pKa Acid
7.22
pKa Basic
-1.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9762
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9762
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.9212
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.9212
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8996
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8996
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8933
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8933
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8912
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8912
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8901
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8901
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8789
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8789
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8541
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8541
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8519
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8519
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8369
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8369
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8274
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8274
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8262
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8262
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8246
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8246
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8175
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8175
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8090
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8090
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8043
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8043
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8020
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8020
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7964
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7964
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7956
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7956
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7922
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7922
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7914
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7914
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7907
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7907
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7757
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7757
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7755
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7755
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7748
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7748
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7708
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7708
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7686
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7686
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.7674
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.7674
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7636
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7636
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7607
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7607
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7579
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7579
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7569
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7569
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7555
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7555
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7554
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7554
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7554
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7554
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7510
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7510
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7500
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7500
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7459
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7459
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7429
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7429
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7415
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7415
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7367
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7367
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7351
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7351
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7343
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7343
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7337
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7337
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7335
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7335
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7333
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7333
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7328
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7328
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7312
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7312
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7186
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7186
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7159
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7159
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7151
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7151
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7144
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7144
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7105
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7105
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7096
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7096
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7091
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7091
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7082
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7082
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7078
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7078
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7059
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7059
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7058
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7058
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7054
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7054
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7028
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7028
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7007
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7007

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