Quercetin 3-O-glucoside

  • GreenMolBD CID : 1
  • Molecular Formula : C21H20O12
  • Molecular Weight : 464.379
  • Exact Molecular Mass : 464.095
  • IUPAC Name : 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
  • InChI : InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1
  • InChI Key : OVSQVDMCBVZWGM-QSOFNFLRSA-N
  • Canonical SMILES : C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O
  • Isomeric SMILES : c1cc(c(cc1c2c(c(=O)c3c(cc(cc3o2)O)O)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O)O)O
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

1.2. Taxonomy Tree

1.3. Alternative Parent

3'-hydroxyflavonoids; 4'-hydroxyflavonoids; 5-hydroxyflavonoids; 7-hydroxyflavonoids; Flavones; Hexoses; O-glycosyl compounds; Chromones; Catechols; 1-hydroxy-2-unsubstituted benzenoids; 1-hydroxy-4-unsubstituted benzenoids; Pyranones and derivatives; Oxanes; Benzene and substituted derivatives; Vinylogous acids; Heteroaromatic compounds; Secondary alcohols; Acetals; Oxacyclic compounds; Polyols; Organic oxides; Primary alcohols; Hydrocarbon derivatives;

1.4. Molecular Framework

Aromatic heteropolycyclic compounds

1.5. Substituents

Flavonoid-3-o-glycoside; Hydroxyflavonoid; 3'-hydroxyflavonoid; 4'-hydroxyflavonoid; 5-hydroxyflavonoid; 7-hydroxyflavonoid; Flavone; Hexose monosaccharide; Chromone; Glycosyl compound; O-glycosyl compound; Benzopyran; 1-benzopyran; Catechol; 1-hydroxy-2-unsubstituted benzenoid; Phenol; Pyranone; 1-hydroxy-4-unsubstituted benzenoid; Monocyclic benzene moiety; Benzenoid; Pyran; Monosaccharide; Oxane; Vinylogous acid; Heteroaromatic compound; Secondary alcohol; Organoheterocyclic compound; Oxacycle; Polyol; Acetal; Hydrocarbon derivative; Organic oxide; Organic oxygen compound; Alcohol; Primary alcohol; Organooxygen compound; Aromatic heteropolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
-0.7306 206.6 8 12 33 4 12 12 10.6274 531.353 396.082 0.873955

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-464.043852 19.78 -1.1 -4.03316 1.83355 2.933

4. Compound Reactivity

DLP nRFG nLMR
4 1 8

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Non-Carcinogen Non-Mutagen Toxic 0.846437 63.7936 0.0749373 None None Moderate Degradable 0.773465 4.01432

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
No No Yes No Yes No Yes

7. Synonyms

Name
Isoquercitrin
Isoquercetin
Hirsutrin
482-35-9
3-Glucosylquercetin
Quercetin 3-o-glucopyranoside
Glucosyl 3-quercetin
Quercetin 3-glucoside
Quercetol 3-glucoside
Quercetin 3-D-glucoside
Quercetin 3-monoglucoside
Quercetol 3-monoglucoside
Isotrifoliin
Quercetin 3-beta-glucoside
Quercetin 3-O-glucoside
quercetin-3-glucoside
CONTIGOSIDE B
Quercetin 3-beta-O-glucoside
Quercetin-3-O-glucopyranoside
UNII-6HN2PC637T
quercetin-3-O-glucoside
quercetin 3-O-beta-D-glucopyranoside
NSC 115918
BRN 0100989
CHEMBL250450
CHEBI:68352
MFCD00017746
NSC-407304
isoquercitin
Q 5
3,3',4',5,7-Pentahydroxyflavone 3-beta-glucoside
2-(3,4-Dihidroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl beta-D-glucopyranoside
4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-
Quercetin-3-galactoside
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMR000466391
Quercetin 3-beta-D-glucoside
BIDF1022
hydroside
CCRIS 9340
Isoquercitrin (6)
ACACIA
AC1NQXMB
3-glucoside isoquercitrin
D04PBH
Quercetin 3-b-D-glucoside
3-beta-D-Glucosylquercetin
Quercetin 3-glucopyranoside
Quercetin 3- -D-glucoside
Quercetin 3-|A-D-glucoside
4-18-00-03493 (Beilstein Handbook Reference)
MLS000759532
MLS001424096
SCHEMBL181306
6HN2PC637T
ACon1_002134
cid_5280804
cid_5378597
MolPort-001-740-247
OVSQVDMCBVZWGM-QSOFNFLRSA-N
ZX-AFC000122
BDBM153265
HMS2051B17
quercetin-3-o-beta-glucopyranoside
ZINC4096845
BDBM50241354
PDSP1_001363
PDSP2_001347
AKOS015896729
Quercetin - 3 - O - glucopyranoside
API0004007
CCG-100967
DB12665
MCULE-2852848721
NC00217
Quercetin-3-O-beta-D-galactopyranoside
Quercetin 3-O-.beta.-D-glucopyranoside
quercetin -3-O-beta-D-galactopyranoside
CA008713
CPD000466391
DR002883
LS-39589
SAM001246767
Quercetin 3-glucoside, analytical standard
NP-000212
FT-0686644
V0296
C05623
AB00639942-06
Quercetin 3-beta-D-glucoside, >=90% (HPLC)
3,3',4',5,7-Pentahydroxyflavone 3- -glucoside
3-Glucopyranosyloxy-3',4',5,7-tetrahydroxyflavone
I07-0180
Q-100268
BRD-K73991644-001-01-7
3,3'',4'',5,7-pentahydroxyflavone-3-beta-O-glucoside
Isoquercitrin, primary pharmaceutical reference standard
2-(3,4-dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one
2-Hydroxy-4-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl b-D-glucopyranoside
4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-3-(b-D-glucopyranosyloxy)-5,7-dihydroxy-
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromen-4-one
2-(3,4-Dihydroxyphenyl)-3-(b-D-glucopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one, 9CI
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
3,3 inverted exclamation marka,4 inverted exclamation marka,5,7-Pentahydroxyflavone 3-|A-glucoside
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxy-phenyl)-3-(.beta.-D-glucofuranosyloxy)-5,7-dihydroxy-
4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-
Quercetin-3-O-beta-D-glucopyranoside
Quercetin glucoside
BG01751666
1012316-11-8
107438-55-1
1246962-26-4
27215-07-2
28454-82-2
355806-24-5
478367-76-9
61277-38-1
888937-01-7

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Quercetin 3-O-glucoside
Abelmoschus esculentus (L.) Moench Skin 1 , 2
Acacia catechu Willd. Leaf 5
Acacia nilotica (L.) Wild. Flower 7 , 11
Acalypha indica L. Flower; Leaf 8
Apium graveolens Seed 7
Arachis hypogea L. Root 4
Coriandrum sativum Linn. Vegetative; Fruit 22
Cucumis sativus L. Flower 9
Cuscuta reflexa Whole Plant 4
Drosera burmanii Aerial 1 , 2
Echinochloa cruss-galli Grain 1 , 2
Flacourtia indica Fruit 9
Hemidesmus indicus br. Flower 19
Ichnocarpus frutescens Flower 5
Impatiens balsamina L.  Petal; Aerial 1 , 11
Jasminum graniflorum Aerial; Leaf 8 , 12 , 20
Lagenaria siceraria (Molina) Standl.  Fruit 2 , 6 , 12
Litchi chinensis Fruit 3
Mangifera indica Peel; Pulp; Seed 2 , 3
Marsilea quadrifolia 2
Phaseolus vulgaris Seed 4
Ricinus communis Leaf 7 , 4 , 5
Rosa damascena Petal 1
Viola odorata Flower 1

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
1 Acetylcholinesterase Homo sapiens 84840
2 aldo-keto reductase family 1 member B Akr1b1 Rattus norvegicus 4.4 654333
2 aldo-keto reductase family 1 member B AKR1B1 Homo sapiens 4.5 639825
2 aldo-keto reductase family 1 member B AKR1B1 Sus scrofa 16 354608
3 alkaline phosphatase, biomineralization associated ALPL Homo sapiens 14 488906
4 alkaline phosphatase, germ cell ALPPL2 Homo sapiens 100 488879
5 alkaline phosphatase, intestinal ALPI Homo sapiens 5.25 463135
5 alkaline phosphatase, intestinal ALPI Homo sapiens 8.96 488876
5 alkaline phosphatase, intestinal Alpi Mus musculus 1.66 488785
6 ATP-dependent phosphofructokinase Tb927.3.3270 Trypanosoma brucei brucei TREU927 26.8545 485367
7 carbonic anhydrase 1 CA1 Homo sapiens 10 1254155
7 carbonic anhydrase 1 CA1 Homo sapiens 10 1254160
8 carbonic anhydrase 12 CA12 Homo sapiens 0.0521 1254159
8 carbonic anhydrase 12 CA12 Homo sapiens 0.17 1254163
9 carbonic anhydrase 2 CA2 Homo sapiens 0.41 1254161
9 carbonic anhydrase 2 CA2 Homo sapiens 6.2112 1254156
10 carbonic anhydrase 4 CA4 Homo sapiens 0.0757 1254157
11 DNA polymerase beta POLB Homo sapiens 1.7783 485314
12 epoxide hydrolase 2 EPHX2 Homo sapiens 28.43 1126472
13 fms related tyrosine kinase 3 FLT3 Homo sapiens 10 730328
14 glucosidase alpha, acid GAA Homo sapiens 3.5481 2100
15 glycogen synthase kinase 3 beta GSK3B Homo sapiens 15.8 434954
16 microtubule associated protein tau MAPT Homo sapiens 15.8489 1460
17 muscleblind like splicing regulator 1 MBNL1 Homo sapiens 10 2675
18 pancreatic lipase PNLIP Sus scrofa 70 1204217
19 Protein-tyrosine phosphatase 1B (PTP1B) Homo sapiens 100000
20 Serine/threonine-protein kinase Aurora-B Homo sapiens 1.07E+4 10.1111/cbdd.12445 25298094
21 thioredoxin glutathione reductase Smp_048430 Schistosoma mansoni 11.2202 485364

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
318366573CambridgeChemSource URLSource DetailDB10069Source Record URL
318046018iChemical Technology USA IncSource URLSource DetailEBD46999Source Record URL
310279515Glentham Life Sciences Ltd.Source URLSource DetailGC9169Source Record URL
355198944MuseChemSource URLSource DetailR063758Source Record URL
104225237ISpharmSource URLSource DetailI07-0180Source Record URL
322076739Pi ChemicalsSource URLSource DetailPI-18339Source Record URL
274951751ChemFacesSource URLSource DetailCFN98753Source Record URL
46386780NIH Clinical CollectionSource URLSource DetailSAM001246767Source Record URL
340522738ChemShuttleSource URLSource Detail181523Source Record URL
3571009351717 CheMall CorporationSource URLSource DetailBG01751666Source Record URL
3599475001717 CheMall CorporationSource URLSource DetailBG06788788Source Record URL
3632756261717 CheMall CorporationSource URLSource DetailBG08009460Source Record URL
3632756251717 CheMall CorporationSource URLSource DetailBG08009471Source Record URL
254770829Boc SciencesSource URLSource Detail21637-25-2Source Record URL
152036148AKos Consulting & SolutionsSource URLSource DetailAKOS015896729Source Record URL
374052568Combi-BlocksSource URLSource DetailQC-6151Source Record URL
319032074Chem-Space.com DatabaseSource URLSource DetailCSC020610449Source Record URL
257139791ZINCSource URLSource DetailZINC4096845Source Record URL
252406204MolepediaSource URLSource DetailM90011872PSource Record URL
162187641AK Scientific, Inc. (AKSCI)Source URLSource DetailV0296Source Record URL
251917137AvaChem ScientificSource URLSource Detail2331Source Record URL
251915789AvaChem ScientificSource URLSource Detail482-35-9Source Record URL
310121993Aurora Fine Chemicals LLCSource URLSource DetailA17.894.276Source Record URL
290041455Aurora Fine Chemicals LLCSource URLSource DetailK05.568.173Source Record URL
319545151Oakwood ProductsSource URLSource Detail099483Source Record URL
316963019ParchemSource URLSource Detail14229Source Record URL
316964134ParchemSource URLSource Detail20311Source Record URL
329747007Sigma-AldrichSource URLSource Detail00140585_SIALSource Record URL
329751314Sigma-AldrichSource URLSource Detail16654_SIALSource Record URL
57647673Sigma-AldrichSource URLSource Detail17793_SIGMASource Record URL
252351046AHH Chemical co.,ltdSource URLSource DetailMT-52983Source Record URL
336350710Angene ChemicalSource URLSource DetailAGN-PC-0RYY9LSource Record URL
88783232MolPortSource URLSource DetailMolPort-001-740-247Source Record URL
349074520Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0592666Source Record URL
346556233LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN01377964Source Record URL
252949441MculeSource URLSource DetailMCULE-2852848721Source Record URL
252216710Race ChemicalSource URLSource DetailRV022505340Source Record URL
255344859BiosynthSource URLSource DetailQ-100268Source Record URL
29204518R&D ChemicalsSource URLSource Detail1327Source Record URL
57357880NovoSeekSource URLSource Detail5280804Source Record URL
329978285Acorn PharmaTech Product ListSource URLSource DetailACN-035731Source Record URL
316430020abcr GmbHSource URLSource DetailAB171935Source Record URL
162250107Chembase.cnSource URLSource Detail155969Source Record URL
164776921Finetech Industry LimitedSource URLSource DetailFT-0686644Source Record URL
350095788DC ChemicalsSource URLSource DetailDCZ-136Source Record URL
113854030ABI ChemSource URLSource DetailAC1NQXMBSource Record URL
368485382AmbinterSource URLSource DetailAmb22168346Source Record URL
374243638Key Organics/BIONETSource URLSource DetailAS-35335Source Record URL