Hyperoside

  • GreenMolBD CID : 129
  • 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,5R,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-DTGCRPNFSA-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)OC4C(C(C(C(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
-492.422815 19.52 -1.075 -3.98445 1.83454 2.909

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
Hyperoside
Hyperin
482-36-0
Quercetin 3-galactoside
Quercetin-3-O-galactoside
Hyperosid
Hyperozide
Jyperin
Quercetin 3-O-beta-D-galactopyranoside
Quercetin 3-D-galactoside
Hyperasid
UNII-8O1CR18L82
QUERCETIN 3-B-D-GALACTOSIDE
Quercetin 3-beta-D-galactopyranoside
quercetin galactoside
quercetin 3-O-galactoside
NSC 407304
Quercetin-3-galactoside
CHEMBL251254
CHEBI:67486
8O1CR18L82
MFCD00016933
2-(3,4-Dihydroxyphenyl)-3-(beta-D-galactopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(.beta.-D-galactopyranosyloxy)-5,7-dihydroxy-
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
CCRIS 9339
p Hyperin
Quercetin 3-.beta.-D-galactopyranoside
Quercetin 3-O-.beta.-D-galactopyranoside
Hyperin (8CI)
AC1NQYSS
quercetin-3-d-galactoside
BIDD:PXR0057
MLS000759538
MEGxp0_000392
SCHEMBL1250514
ACon1_000623
MolPort-001-740-566
OVSQVDMCBVZWGM-DTGCRPNFSA-N
Quercetin 3-O-beta-D-galactoside
HMS2051H17
ZINC3973253
BDBM50241367
AKOS015896780
AN-8426
CCG-100970
MCULE-5363142212
NC00220
BC209737
BT000834
CA002659
CA010017
CC-29452
CPD000466394
DR002881
S600
SAM001246776
SC-43872
SMR000466394
NP-001009
FT-0082599
FT-0603413
N1838
C10073
Quercetin 3-D-galactoside, >=97.0% (HPLC)
AB00639910-03
482H360
C-22630
3,3',4',5,7-Pentahydroxyflavone 3-D-galactoside
Hyperoside, primary pharmaceutical reference standard
I07-0250
Q-100530
BRD-K84955386-001-01-1
3-O-b-D-Galactopyranosyloxy-3',4',5,7-tetrahydroxyflavone
Hyperoside, United States Pharmacopeia (USP) Reference Standard
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl beta-D-galactopyranoside
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl hexopyranoside #
4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-3-(b-D-galactopyranosyloxy)-5,7-dihydroxy-
112457-37-1
158560-10-2
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-((2S,4R,5R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromen-4-one
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
26857-03-4
28986-85-8
29224-70-2
3,3 inverted exclamation marka,4 inverted exclamation marka,5,7-Pentahydroxyflavone 3-D-galactoside
31710-72-2
56552-81-9
61277-37-0
63003-36-1
71184-39-9

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Hyperoside
Abelmoschus esculentus (L.) Moench 6
Coriandrum sativum Linn. Grass 9
Croton oblongifolius  Leaf 14
Cuscuta reflexa Whole Plant 4
Drosera burmanii Aerial 1 , 2 , 3
Duabanga grandiflora Stem 1
Hemidesmus indicus br. Flower 19
Juglans regia Leaf 17
Mangifera indica Peel; Pulp; Seed 2 , 3
Ricinus communis Flower 10 , 4

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
2 aldo-keto reductase family 1 member B AKR1B1 Homo sapiens 3 639825
6 ATP-dependent phosphofructokinase Tb927.3.3270 Trypanosoma brucei brucei TREU927 6.7456 485367
119 bromodomain adjacent to zinc finger domain 2B BAZ2B Homo sapiens 79.4328 504333
162 cyclin dependent kinase 5 CDK5 Homo sapiens 10.28 767308
163 cyclin dependent kinase 5 regulatory subunit 1 CDK5R1 Homo sapiens 10.28 767308
11 DNA polymerase beta POLB Homo sapiens 5.0119 485314
12 epoxide hydrolase 2 EPHX2 Homo sapiens 21.76 1126472
164 galactosidase alpha GLA Homo sapiens 35.4813 2107
14 glucosidase alpha, acid GAA Homo sapiens 35.4813 2112
14 glucosidase alpha, acid GAA Homo sapiens 6.3096 2100
73 glucosylceramidase beta GBA Homo sapiens 25.1189 2101
28 lamin A/C LMNA Homo sapiens 28.1838 1487
16 microtubule associated protein tau MAPT Homo sapiens 31.6228 1460
86 mitogen-activated protein kinase 1 MAPK1 Homo sapiens 39.8107 1454
17 muscleblind like splicing regulator 1 MBNL1 Homo sapiens 28.1838 2675

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
252359127AHH Chemical co.,ltdSource URLSource DetailAPI-1458Source Record URL
329747012Sigma-AldrichSource URLSource Detail00180585_SIALSource Record URL
329750143Sigma-AldrichSource URLSource Detail1335202_USPSource Record URL
57652957Sigma-AldrichSource URLSource Detail83388_SIGMASource Record URL
274951750ChemFacesSource URLSource DetailCFN98754Source Record URL
318267422Chem-Space.com DatabaseSource URLSource DetailCSC000052393Source Record URL
57358276NovoSeekSource URLSource Detail5281643Source Record URL
316469704abcr GmbHSource URLSource DetailAB253879Source Record URL
329978039Acorn PharmaTech Product ListSource URLSource DetailACN-035463Source Record URL
46386811NIH Clinical CollectionSource URLSource DetailSAM001246776Source Record URL
310119037Aurora Fine Chemicals LLCSource URLSource DetailA17.891.320Source Record URL
290041643Aurora Fine Chemicals LLCSource URLSource DetailK05.568.437Source Record URL
255345116BiosynthSource URLSource DetailQ-100530Source Record URL
252949755MculeSource URLSource DetailMCULE-5363142212Source Record URL
104225307ISpharmSource URLSource DetailI07-0250Source Record URL
348354105AbMole BioscienceSource URLSource DetailM4004Source Record URL
252406205MolepediaSource URLSource DetailM90011873PSource Record URL
368511613AmbinterSource URLSource DetailAmb21855883Source Record URL
252215558Race ChemicalSource URLSource DetailRV022504188Source Record URL
355173079MuseChemSource URLSource DetailR010828Source Record URL
318241503Yuhao ChemicalSource URLSource DetailLQ0900Source Record URL
126624006ChemMolSource URLSource Detail30104992Source Record URL
126655301ChemMolSource URLSource Detail44003758Source Record URL
126664266ChemMolSource URLSource Detail49402830Source Record URL
163614412ApexBio TechnologySource URLSource DetailN1838Source Record URL
251911821AvaChem ScientificSource URLSource Detail1148Source Record URL
118048596Finetech Industry LimitedSource URLSource DetailFT-0082599Source Record URL
164788592Finetech Industry LimitedSource URLSource DetailFT-0603413Source Record URL
223671062AN PharmaTechSource URLSource DetailAN-8426Source Record URL
322078622Pi ChemicalsSource URLSource DetailPI-20406Source Record URL
254777681Boc SciencesSource URLSource Detail482-36-0Source Record URL
162250054Chembase.cnSource URLSource Detail155916Source Record URL
251885549labseekerSource URLSource DetailSC-43872Source Record URL
3571009341717 CheMall CorporationSource URLSource DetailBG01751665Source Record URL
3599474991717 CheMall CorporationSource URLSource DetailBG06788787Source Record URL
257100665ZINCSource URLSource DetailZINC3973253Source Record URL
310279513Glentham Life Sciences Ltd.Source URLSource DetailGC9523Source Record URL
350089632DC ChemicalsSource URLSource DetailDCJ-012Source Record URL
113855559ABI ChemSource URLSource DetailAC1NQYSSSource Record URL
162185971AK Scientific, Inc. (AKSCI)Source URLSource DetailS600Source Record URL
152036199AKos Consulting & SolutionsSource URLSource DetailAKOS015896780Source Record URL
196110590BoerchemSource URLSource DetailBC209737Source Record URL
318366578CambridgeChemSource URLSource DetailDB10052Source Record URL
341836917OChemSource URLSource Detail6770Source Record URL
347260563LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN01345107Source Record URL
88783551MolPortSource URLSource DetailMolPort-001-740-566Source Record URL
349074521Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0592667Source Record URL
315446060Phion LtdSource URLSource Detail64405544Source Record URL
312694772TargetMolSource URLSource DetailT2844Source Record URL