Kaempferol-3-O-beta-glucopyranoside

  • GreenMolBD CID : 719
  • Molecular Formula : C21H20O11
  • Molecular Weight : 448.38
  • Exact Molecular Mass : 448.101
  • IUPAC Name : 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
  • InChI : InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15-,17+,18-,21+/m1/s1
  • InChI Key : JPUKWEQWGBDDQB-QSOFNFLRSA-N
  • Canonical SMILES : C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O
  • Isomeric SMILES : c1cc(ccc1c2c(c(=O)c3c(cc(cc3o2)O)O)OC4C(C(C(C(O4)CO)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

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

1.4. Molecular Framework

Aromatic heteropolycyclic compounds

1.5. Substituents

Flavonoid-3-o-glycoside; 4'-hydroxyflavonoid; 5-hydroxyflavonoid; 7-hydroxyflavonoid; Flavone; Hydroxyflavonoid; Hexose monosaccharide; Chromone; Glycosyl compound; O-glycosyl compound; Benzopyran; 1-benzopyran; 1-hydroxy-4-unsubstituted benzenoid; 1-hydroxy-2-unsubstituted benzenoid; Phenol; Pyranone; Pyran; Monocyclic benzene moiety; Oxane; Monosaccharide; Benzenoid; Heteroaromatic compound; Vinylogous acid; Secondary alcohol; Organoheterocyclic compound; Oxacycle; Acetal; Polyol; 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
-0.4362 186.37 7 11 32 4 12 12 10.4609 522.831 386.052 0.8576

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-403.415203 2.95 -4.76 -8.9916 -0.52925 4.231

4. Compound Reactivity

DLP nRFG nLMR
1 1 7

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 0.694919 108.8 0.0561534 None None Moderate Degradable 0.431304 4.33174

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 Yes Yes

7. Synonyms

Name
Astragalin
480-10-4
Astragaline
kaempferol-3-glucoside
Kaempferol 3-glucoside
Kaempferol 3-O-glucoside
Kaempferol-3-O-glucoside
asragalin
Kaempferol-3-beta-monoglucoside
Kaempferol-3-D-glucoside
Kaempferol-3-beta-glucopyranoside
UNII-APM8UQ3Z9O
3,4',5,7-Tetrahydroxyflavone-3-glucoside
Kaempferol 3-O-beta-D-glucopyranoside
3-Glucosylkaempferol
Kaempferol 3-O-beta-D-glucoside
APM8UQ3Z9O
4H-1-Benzopyran-4-one, 3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
CHEMBL233930
CHEBI:30200
JPUKWEQWGBDDQB-QSOFNFLRSA-N
MFCD00075932
K5
3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl beta-D-glucopyranoside
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
Kaempferol 3-beta-D-glucopyranoside, >=97.0% (HPLC)
Astraglin
AC1NQZH5
3-O-b-D-Glucopyranoside
D08BFU
SCHEMBL23897
MLS002473092
MEGxp0_000168
ACon1_001224
cid_5282102
MolPort-001-740-346
BDBM226182
HMS2227A14
Kaempferol 3-|A-D-glucopyranoside
HY-N0015
Kaempferol 3-beta-D-glucopyranoside
kaempferol-3-O-beta-glucopyranoside
ZINC4102435
BDBM50241243
Kaempferol 3-O-|A-D-glucopyranoside
AKOS015896779
API0003066
CS-3720
EBD2185051
Kaempferol 3-O-beta-D-glucoside (6)
MCULE-5200434087
Kaempferol-3-O-.beta.-D-glucopyranoside
NCGC00163580-01
NCGC00163580-02
AN-45177
BT000795
CA010010
CC-24200
LS-39675
SC-46057
SMR001397194
Kaempferol 3-glucoside, analytical standard
NP-000437
3,4'',5,7-Tetrahydroxyflavone-3-glucoside
FT-0602874
N1897
C12249
480A104
C-22455
I07-0247
Q-100517
3-O-b-D-Glucopyranosyloxy-4',5,7-trihydroxyflavone
BRD-K44487476-001-01-5
Kaempferol 3-glucoside, primary pharmaceutical reference standard
3-(|A-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
3-(beta-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one,3-(b-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl .beta.-D-glucopyranoside
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Kaempferol-3-O-beta-D-glucopyranoside
Kaempferol 3-O-beta-glucoside
Kaempferol-3-O-glycoside
Kaempherol-3-glucoside
BG01739208
SR-05000002271
SR-05000002271-2

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Kaempferol-3-O-beta-glucopyranoside
Ammannia baccifera L. Whole Plant 4
Anthocephalus chinesis (Lamk.) Rich. Ex Walp. Leaf 3
Bauhinia variegate Aerial; Root Bark 1 , 3 , 4
Coriandrum sativum Linn. 36
Crocus sativus L. Petal; Stigma 12 , 16 , 17
Cucumis sativus L. Flower 9
Impatiens balsamina L.  Petal; Flower 1 , 3 , 4
Mangifera indica Peel; Pulp; Seed 2 , 3
Marsilea quadrifolia 2
Melastoma malabathricum Flower 5 , 4 , 15
Microcos paniculata Leaf 3
Phaseolus vulgaris Seed 2 , 3 , 4
Ricinus communis Leaf 7 , 4 , 5

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 Rattus norvegicus 5.09 385353
2 aldo-keto reductase family 1 member B AKR1B1 Homo sapiens 60.5 639825
229 apical membrane antigen 1 AMA1 Plasmodium falciparum 3D7 3.1623 720542
190 ATPase family, AAA domain containing 5 ATAD5 Homo sapiens 14.575 504467
739 BCL2 like 11 BCL2L11 Homo sapiens 350 2765
7 carbonic anhydrase 1 CA1 Homo sapiens 10 1254155
8 carbonic anhydrase 12 CA12 Homo sapiens 0.0049 1254159
9 carbonic anhydrase 2 CA2 Homo sapiens 0.168 1254156
10 carbonic anhydrase 4 CA4 Homo sapiens 5.5912 1254157
130 carbonic anhydrase 7 CA7 Homo sapiens 0.4237 1254158
65 DNA polymerase iota POLI Homo sapiens 89.1251 588590
667 dual specificity tyrosine phosphorylation regulated kinase 1A Dyrk1a Rattus norvegicus 6.739 588345
12 epoxide hydrolase 2 EPHX2 Homo sapiens 50 1126472
259 glycogen synthase kinase 3 alpha GSK3A Homo sapiens 30.36 463203
1149 glycoprotein hormones, alpha polypeptide CGA Homo sapiens 5.0119 624291
90 karyopherin subunit beta 1 KPNB1 Homo sapiens 0.0041 540253
18 pancreatic lipase PNLIP Sus scrofa 70 1204217
361 parathyroid hormone 1 receptor PTH1R Homo sapiens 100 743266
1107 prolyl 4-hydroxylase subunit beta P4HB Homo sapiens 19.02 602350
1107 prolyl 4-hydroxylase subunit beta P4HB Homo sapiens 19.02 624274
181 RAN, member RAS oncogene family RAN Homo sapiens 0.0041 540253
185 Rap guanine nucleotide exchange factor 3 RAPGEF3 Homo sapiens 39.8107 720709
91 snurportin 1 SNUPN Homo sapiens 0.0041 540253

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
3570884771717 CheMall CorporationSource URLSource DetailBG01739208Source Record URL
3599312061717 CheMall CorporationSource URLSource DetailBG06775385Source Record URL
254760988Boc SciencesSource URLSource Detail480-10-4Source Record URL
329747937Sigma-AldrichSource URLSource Detail04500585_SIALSource Record URL
329756432Sigma-AldrichSource URLSource Detail43951_SIGMASource Record URL
329760906Sigma-AldrichSource URLSource Detail68437_SIALSource Record URL
329768655Sigma-AldrichSource URLSource Detail79851_SIGMASource Record URL
223671015AN PharmaTechSource URLSource DetailAN-45177Source Record URL
318482353Herbest Bio-TechSource URLSource DetailHA020488Source Record URL
57358512NovoSeekSource URLSource Detail5282102Source Record URL
29204307R&D ChemicalsSource URLSource Detail1243Source Record URL
162220309Chembase.cnSource URLSource Detail125966Source Record URL
152036198AKos Consulting & SolutionsSource URLSource DetailAKOS015896779Source Record URL
318366574CambridgeChemSource URLSource DetailDB10010Source Record URL
254804493MedChemexpress MCESource URLSource DetailHY-N0015Source Record URL
251866334labseekerSource URLSource DetailSC-46057Source Record URL
251916930AvaChem ScientificSource URLSource Detail2117Source Record URL
251915580AvaChem ScientificSource URLSource Detail480-10-4Source Record URL
104225304ISpharmSource URLSource DetailI07-0247Source Record URL
350090386DC ChemicalsSource URLSource DetailDCZ-020Source Record URL
316469763abcr GmbHSource URLSource DetailAB253946Source Record URL
223485078Wolves R&D chemicalSource URLSource DetailEBD2185051Source Record URL
354300698iChemical Technology USA IncSource URLSource DetailEBD2185051Source Record URL
126688768ChemMolSource URLSource Detail49427418Source Record URL
241080368ChemMolSource URLSource Detail99089472Source Record URL
163614292ApexBio TechnologySource URLSource DetailN1897Source Record URL
113856436ABI ChemSource URLSource DetailAC1NQZH5Source Record URL
255345103BiosynthSource URLSource DetailQ-100517Source Record URL
252949514MculeSource URLSource DetailMCULE-5200434087Source Record URL
257141823ZINCSource URLSource DetailZINC4102435Source Record URL
252406174MolepediaSource URLSource DetailM90011785PSource Record URL
164788053Finetech Industry LimitedSource URLSource DetailFT-0602874Source Record URL
348354759AbMole BioscienceSource URLSource DetailM4668Source Record URL
88783331MolPortSource URLSource DetailMolPort-001-740-346Source Record URL
310132053Aurora Fine Chemicals LLCSource URLSource DetailA17.904.337Source Record URL
290041509Aurora Fine Chemicals LLCSource URLSource DetailK05.568.256Source Record URL
341842479OChemSource URLSource Detail12351Source Record URL
319553810AbovChem LLCSource URLSource DetailHY-N0015Source Record URL
274951771ChemFacesSource URLSource DetailCFN98733Source Record URL
349073954Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0592100Source Record URL
312324272AbaChemSceneSource URLSource DetailCS-3720Source Record URL
347258484LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN01341834Source Record URL
310275599Glentham Life Sciences Ltd.Source URLSource DetailGL9890Source Record URL
340124377Acorn PharmaTech Product ListSource URLSource DetailACN-047171Source Record URL
355037455MuseChemSource URLSource DetailI003685Source Record URL
318267094Chem-Space.com DatabaseSource URLSource DetailCSC000051335Source Record URL
252359121AHH Chemical co.,ltdSource URLSource DetailAPI-1452Source Record URL
252214895Race ChemicalSource URLSource DetailRV022503525Source Record URL