Isovitexin

  • GreenMolBD CID : 1591
  • Molecular Formula : C21H20O10
  • Molecular Weight : 432.381
  • Exact Molecular Mass : 432.106
  • IUPAC Name : 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
  • InChI : InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21+/m1/s1
  • InChI Key : MYXNWGACZJSMBT-VJXVFPJBSA-N
  • Canonical SMILES : C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O)C4C(C(C(C(O4)CO)O)O)O)O)O
  • Isomeric SMILES : c1cc(ccc1c2cc(=O)c3c(o2)cc(c(c3O)C4C(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 c-glycosides. These are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

1.2. Taxonomy Tree

1.3. Alternative Parent

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

1.4. Molecular Framework

Aromatic heteropolycyclic compounds

1.5. Substituents

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

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
0.03 177.14 7 10 31 3 12 12 10.3645 512.17 371.049 0.844214

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-369.462864 5.1 -4.727 -8.96155 -0.49328 4.234

4. Compound Reactivity

DLP nRFG nLMR
1 0 9

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 1.05068 146.404 0.0401375 None None Severe Degradable 0.127553 8.95976

6. Drug-Likeliness Test

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

7. Synonyms

Name
Isovitexin
Saponaretin
Homovitexin
Apigenin-6-C-glucoside
38953-85-4
6-Glucosylapigenin
6-C-Glucosylapigenin
29702-25-8
UNII-KTQ9R9MS0Q
Apigenin 6-C-glucoside
KTQ9R9MS0Q
CHEBI:18330
4H-1-Benzopyran-4-one, 6-beta-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
Isoavroside
(1S)-1,5-anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl]-D-glucitol
SMR001215816
CCRIS 9341
beta-D-isovitexin
Apigenin 6-C-beta-glucopyranoside
Isovitexin with HPLC
ISOVITEXIN WITH
AC1Q6BBK
C01714
AC1L4R4R
MLS000563041
MLS002473147
SCHEMBL513620
Ambap29702-25-8
Isovitexin, analytical standard
CHEMBL465360
Flavone, 6-beta-D-glucopyranosyl-4',5,7-trihydroxy-
MolPort-020-005-945
MYXNWGACZJSMBT-VJXVFPJBSA-N
HMS2268O04
Isovitexin, >=98.0% (HPLC)
ZINC4095704
MFCD00076044
AKOS032948364
CCG-208397
6-b-d-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one
6-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
NCGC00163578-01
4CN-1176
BT000761
CA000959
CA010823
FT-0645081
FT-0686646
W1628
Isovitexin, primary pharmaceutical reference standard
Flavone, 6-.beta.-D-glucopyranosyl-4',5,7-trihydroxy-
4H-1-Benzopyran-4-one, 6-.beta.-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
4H-1-Benzopyran-4-one, 6-beta-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)- (VAN)
4H-1-Benzopyran-4-one,6-b-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
3681-94-5
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one
61383-34-4

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Isovitexin
Biophytum sensitivum (L.) DC. Leaf 2
Colocasia esculenta Linn. Shoot; Leaf 4 , 6
Cucumis sativus L. Leaf 3 , 9
Cyperus rotundus L Aerial 16
Ichnocarpus frutescens Leaf 8
Jatropha gossypifolia Leaf 8 , 10 , 18 , 2 , 19
Lagenaria siceraria (Molina) Standl.  16
Ludwigia octovalvis Leaf 4
Microcos paniculata Leaf 3 , 8
Scoparia dulcia L Whole Plant 16

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
117 ankyrin-like protein B18R Vaccinia virus 1 720579
176 GNAS complex locus GNAS Homo sapiens 4.4668 624287
303 isocitrate dehydrogenase (NADP(+)) 1, cytosolic IDH1 Homo sapiens 29.0929 686970

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
3615571911717 CheMall CorporationSource URLSource DetailBG04713538Source Record URL
252419375MolepediaSource URLSource DetailM90207109PSource Record URL
113449260ABI ChemSource URLSource DetailAC1L4R4RSource Record URL
117587089ABI ChemSource URLSource DetailAC1Q6BBKSource Record URL
274951883ChemFacesSource URLSource DetailCFN98620Source Record URL
57349854NovoSeekSource URLSource Detail162350Source Record URL
29204302R&D ChemicalsSource URLSource Detail1235Source Record URL
329747213Sigma-AldrichSource URLSource Detail01120590_SIALSource Record URL
57647678Sigma-AldrichSource URLSource Detail17804_SIGMASource Record URL
329760418Sigma-AldrichSource URLSource Detail67135_SIALSource Record URL
340124330Acorn PharmaTech Product ListSource URLSource DetailACN-047124Source Record URL
342381695AKos Consulting & SolutionsSource URLSource DetailAKOS032948364Source Record URL
318504990CambridgeChemSource URLSource DetailCB21544Source Record URL
348354837AbMole BioscienceSource URLSource DetailM4746Source Record URL
164780266Finetech Industry LimitedSource URLSource DetailFT-0645081Source Record URL
164776923Finetech Industry LimitedSource URLSource DetailFT-0686646Source Record URL
310121790Aurora Fine Chemicals LLCSource URLSource DetailA17.894.073Source Record URL
355174787MuseChemSource URLSource DetailR039872Source Record URL
251917147AvaChem ScientificSource URLSource Detail2341Source Record URL
251915799AvaChem ScientificSource URLSource Detail38953-85-4Source Record URL
254773230Boc SciencesSource URLSource Detail29702-25-8Source Record URL
350090328DC ChemicalsSource URLSource DetailDCY-116Source Record URL
340472126Ark Pharma Scientific LimitedSource URLSource DetailN-1159Source Record URL
349777405Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM1295549Source Record URL
313226168MolPortSource URLSource DetailMolPort-020-005-945Source Record URL
252550981AK Scientific, Inc. (AKSCI)Source URLSource DetailW1628Source Record URL
103805185AAA ChemistrySource URLSource DetailAR-1H0977Source Record URL
103805186AAA ChemistrySource URLSource DetailAR-1H0978Source Record URL
354313374iChemical Technology USA IncSource URLSource DetailEBD2203343Source Record URL
252350689AHH Chemical co.,ltdSource URLSource DetailMT-52625Source Record URL
257139565ZINCSource URLSource DetailZINC4095704Source Record URL
346552653LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN01344771Source Record URL
2420590164C Pharma Scientific IncSource URLSource Detail4CN-1176Source Record URL
162250085Chembase.cnSource URLSource Detail155947Source Record URL
316469757abcr GmbHSource URLSource DetailAB253940Source Record URL