Quercetin 3-O-rhamnoside - Compound Card

Quercetin 3-O-rhamnoside

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Quercetin 3-O-rhamnoside

Structure
Zoomed Structure
  • Family: Plantae - Tamaricaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles Oc1cc(O)c2c(c1)oc(c(c2=O)OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O)c1ccc(c(c1)O)O
InChI InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21?/m1/s1
InChIKey OXGUCUVFOIWWQJ-GPTQEAJUSA-N
Formula C21H20O11
HBA 11
HBD 7
MW 448.38
Rotatable Bonds 3
TPSA 190.28
LogP 0.49
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 448.1
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Harpephyllum caffrum Anacardiaceae Plantae 289712
2 Melia azedarach Meliaceae Plantae 155640
3 Potamogeton perfoliatus Potamogetonaceae Plantae 55320
4 Tamarix articulata Tamaricaceae Plantae 189786

Showing of synonyms

  • Rezq S, Mahmoud M.F, et al. (2021). Anti-Inflammatory, Antipyretic, and Analgesic Properties of Potamogeton perfoliatus Extract: In Vitro and In Vivo Study. Molecules, 2021, 26(16), 4826. [View] [PubMed]
  • Nawwar M, Hussein S, et al. (2011). Constitutive phenolics of Harpephyllum caffrum (Anacardiaceae) and their biological effects on human keratinocytes. Fitoterapia,2011,82(8),1265-1271. [View] [PubMed]
  • Shaalan Y.M, Handoussa H, et al. (2018). Destabilizing the interplay between miR-1275 and IGF2BPs by Tamarix articulata and quercetin in hepatocellular carcinoma. Nat Prod Res,2018,32(18),2217-2220. [View] [PubMed]
  • DiMeo A, Logendran R, et al. (2024). Navigating the Labyrinth of Pregnancy-Related Coverage for Undocumented Immigrants: An Assessment of Current State and Federal Policies.. American journal of public health, 2024, e1-e10. [View] [PubMed]
Pubchem: 5280459
Kegg Ligand: C01750
Chebi: 17558
Nmrshiftdb2: 60021620
Metabolights: MTBLC17558
Pdb Ligand: QCT
Bindingdb: 50056315
CPRiL: 28255
Structure

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

Level: 2

Mol. Weight: 448.38 g/mol

Structure

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

Level: 1

Mol. Weight: 448.38 g/mol

Structure

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

Level: 1

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 448.38 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 448.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.7
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.61
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.89
Plasma Protein Binding
79.03
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
14.36
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.66
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.21
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.62
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
-61.63
Rat (Acute)
2.36
Rat (Chronic Oral)
3.97
Fathead Minnow
3.71
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
624.84
Hydration Free Energy
-6.04
Log(D) at pH=7.4
0.59
Log(P)
1.11
Log S
-4.12
Log(Vapor Pressure)
-11.28
Melting Point
205.6
pKa Acid
4.65
pKa Basic
7.49
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9685
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9685
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9036
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9036
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9035
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9035
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8983
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8983
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8918
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8918
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8863
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8863
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8727
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8727
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8625
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8625
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8610
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8610
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8552
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8552
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8505
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8505
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8403
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8403
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8313
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8313
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8175
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8175
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.8167
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.8167
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8158
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8158
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8094
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8094
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8074
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8074
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8040
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8040
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7996
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7996
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7938
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7938
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7870
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7870
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7834
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7834
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7790
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7790
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7761
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7761
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7729
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7729
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7671
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7671
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7656
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7656
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7625
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7625
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7583
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7583
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7578
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7578
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7567
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7567
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7564
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7564
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7519
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7519
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7456
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7456
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7448
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7448
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.7437
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.7437
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7417
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7417
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7399
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7399
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7367
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7367
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7365
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7365
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7350
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7350
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7284
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7284
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7258
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7258
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7255
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7255
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7175
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7175
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7161
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7161
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7161
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7161
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.7155
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.7155
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7147
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7147
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7070
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7070
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7064
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7064
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7016
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7016
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7002
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7002

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