Quercetin 3-alpha-L-arabinopyranoside - Compound Card

Quercetin 3-alpha-L-arabinopyranoside

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Quercetin 3-alpha-L-arabinopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Myrtaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)O)O
InChI InChI=1S/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15-,17+,20-/m0/s1
InChIKey PZZRDJXEMZMZFD-IEGSVRCHSA-N
Formula C20H18O11
HBA 11
HBD 7
MW 434.35
Rotatable Bonds 3
TPSA 190.28
LogP 0.1
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 434.08
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Embelia schimperi Primulaceae Plantae 2595069
2 Embelia schimperi Myrsinaceae Plantae 2595069
3 Agelanthus brunneus Loranthaceae Plantae 48922
4 Syzygium samarangense Myrtaceae Plantae 260143

Showing of synonyms

  • Thomas Wieland MK, Pantaleon A, et al. (2021). (‒)-Brunneusine, a new phenolic compound with antibacterial properties in aqueous medium from the leaves of Agelanthus brunneus (Engl.) Tiegh (LORANTHACEAE). Naturforsch C J Biosci, 2021,77(3-4),157-165. [View]
  • Hussein G, Miyashiro H, et al. (2000). Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease. Phytotherapy Research,2000,14(7),510-516. [View] [PubMed]
  • Hussein G, Miyashiro H, et al. (2000). Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease.. Phytotherapy Research,2000,14(7),510-516. [View] [PubMed]
  • Samy M.N, Sugimoto S, et al. (2014). Taxiphyllin 6-O-Gallate, Actinidioionoside 6-O-Gallate and Myricetrin 2-O-Sulfate from the Leaves of Syzygium samarangense and Their Biological Activities. Chemical & pharmaceutical bulletin,2014, 62(10), 1013-8. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 434.35 g/mol

Structure

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

Level: 1

Mol. Weight: 434.35 g/mol

Structure

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

Level: 1

Mol. Weight: 434.35 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 434.35 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 434.35 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 434.35 g/mol

Anti-hcv protease
Antibacterial
Antiviral

Absorption

Caco-2 (logPapp)
-6.35
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.67
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.89
Plasma Protein Binding
85.29
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
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
13.81
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.01
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.17
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.62
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
-42.05
Rat (Acute)
2.45
Rat (Chronic Oral)
3.67
Fathead Minnow
3.86
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
612.77
Hydration Free Energy
-7.62
Log(D) at pH=7.4
0.38
Log(P)
0.97
Log S
-4.17
Log(Vapor Pressure)
-10.83
Melting Point
229.35
pKa Acid
5.92
pKa Basic
7.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8958
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8958
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8921
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8921
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8911
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8911
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8787
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8787
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8733
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8733
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8649
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8649
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8626
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8626
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8574
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8574
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8529
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8529
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8525
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8525
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8512
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8512
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8502
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8502
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8486
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8486
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8439
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8439
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8253
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8253
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8235
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8235
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8217
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8217
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8188
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8188
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7995
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7995
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7991
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7991
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7966
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7966
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7961
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7961
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7952
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7952
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7913
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7913
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7909
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7909
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7903
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7903
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7828
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7828
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7816
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7816
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7788
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7788
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7770
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7770
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7747
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7747
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7740
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7740
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7737
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7737
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7687
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7687
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7671
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7671
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7625
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7625
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7611
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7611
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 6 0.7605
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 6 0.7605
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7602
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7602
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7569
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7569
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7538
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7538
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7509
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7509
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7489
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7489
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7464
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7464
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7377
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7377
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7345
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7345
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7342
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7342
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7338
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7338
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7294
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7294
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7265
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7265
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7241
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7241
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7224
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7224
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7220
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7220
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7207
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7207
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7183
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7183
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7180
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7180
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7174
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7174
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7172
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7172
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7160
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7160
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7154
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7154
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.7148
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.7148
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7141
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7141
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7141
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7141
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7111
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7111
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7073
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7073
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 4 0.7049
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 4 0.7049
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7040
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7040
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7037
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7037
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7029
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7029
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7020
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7020
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7004
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7004

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