Vitexin

  • GreenMolBD CID : 511
  • Molecular Formula : C21H20O10
  • Molecular Weight : 432.381
  • Exact Molecular Mass : 432.106
  • IUPAC Name : 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(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(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1
  • InChI Key : SGEWCQFRYRRZDC-VPRICQMDSA-N
  • Canonical SMILES : C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)O)O
  • Isomeric SMILES : c1cc(ccc1c2cc(=O)c3c(cc(c(c3o2)C4C(C(C(C(O4)CO)O)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 8-c-glycosides. These are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 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; 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-8-c-glycoside; Hydroxyflavonoid; 4'-hydroxyflavonoid; 5-hydroxyflavonoid; 7-hydroxyflavonoid; Flavone; Phenolic glycoside; Hexose monosaccharide; Glycosyl compound; C-glycosyl compound; Chromone; 1-benzopyran; Benzopyran; Pyranone; Phenol; 1-hydroxy-2-unsubstituted benzenoid; Pyran; Monosaccharide; Monocyclic benzene moiety; Benzenoid; Oxane; 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
-367.522892 5.42 -4.786 -8.98536 -0.58642 4.199

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 1.08835 146.404 0.0401375 None None Moderate 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
Vitexin
3681-93-4
Apigenin 8-C-glucoside
8-beta-D-Glucopyranosyl-apigenin
EINECS 222-963-8
Flavone, 8-D-glucosyl-4',5,7-trihydroxy-
CHEBI:16954
MFCD00017456
8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
(1S)-1,5-anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-D-glucitol
4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-beta-D-glucopyranosyl-2-(4-hydroxyphenyl)-
4H-1-Benzopyran-4-one, 8-beta-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
5,7-dihydroxy-8-beta-d-glucopyranosyl-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one
UNII-9VP70K75OK
Vitxein
Vitexin HPLC
AC1NQX0Z
Vitexin, analytical standard
SCHEMBL25277
Ambap3681-93-4
9VP70K75OK
CHEMBL487417
CTK8F0956
DTXSID90190287
4H-1-Benzopyran-4-one, 8-.beta.-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
MolPort-003-935-138
SGEWCQFRYRRZDC-VPRICQMDSA-N
Apigenin 8-C-.beta.-D-glucoside
ACT02625
ZINC4245684
BDBM50362886
GC5761
AKOS025311479
AC-6086
CCG-208516
NCGC00163642-01
AN-10375
BT000760
CA000467
CA010206
DR002674
LS-39593
SC-45938
TR-035805
FT-0603644
N1319
V0191
C01460
FLAVONE,8-D-GLUCOSYL-4,5,7-TRIHYDROXY-
681V934
C-22262
Vitexin, primary pharmaceutical reference standard
Q-100437
5,7,4'-Trihydroxyflavone 8-C-.beta.-D-glucopyranoside
Vitexin, United States Pharmacopeia (USP) Reference Standard
4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-.beta.-D-glucopyranosyl-2-(4-hydroxyphenyl)-
4H-1-Benzopyran-4-one,8-b-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-
521-33-5
BG01721469

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Vitexin
Acacia nilotica (L.) Wild. Leaf; Pod; Bark 12
Colocasia esculenta Linn. Shoot; Leaf 4 , 6
Coriandrum sativum Linn. Grass 9
Cyperus rotundus L Aerial 16
Ichnocarpus frutescens Leaf 8
Jatropha gossypifolia Leaf 8 , 10 , 18 , 2 , 19
Ludwigia octovalvis Leaf 4
Microcos paniculata Leaf 3 , 8
Ricinus communis 4
Scoparia dulcia L Whole Plant 16
Tamarindus indica Root 11

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 2.03 1096076
2 aldo-keto reductase family 1 member B AKR1B1 Homo sapiens 566.66 639825
167 Aldose reductase (AR) 566660 10.1016/j.bmc.2011.12.033 22261024
197 DNA polymerase kappa POLK Homo sapiens 23.7781 588579

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
350089847DC ChemicalsSource URLSource DetailDCM-023Source Record URL
342526857Wubei-BiochemSource URLSource DetailWB415828STSource Record URL
252818432AKos Consulting & SolutionsSource URLSource DetailAKOS025311479Source Record URL
92722496Hangzhou APIChem TechnologySource URLSource DetailAC-6086Source Record URL
254775356Boc SciencesSource URLSource Detail3681-93-4Source Record URL
329747149Sigma-AldrichSource URLSource Detail00840595_SIALSource Record URL
329751506Sigma-AldrichSource URLSource Detail1717708_USPSource Record URL
329757466Sigma-AldrichSource URLSource Detail49513_SIALSource Record URL
57357737NovoSeekSource URLSource Detail5280441Source Record URL
318168004labseekerSource URLSource DetailSC-45938Source Record URL
355433484MuseChemSource URLSource DetailR016010Source Record URL
163614514ApexBio TechnologySource URLSource DetailN1319Source Record URL
252359140AHH Chemical co.,ltdSource URLSource DetailAPI-1471Source Record URL
252411600MolepediaSource URLSource DetailM90056687PSource Record URL
164788823Finetech Industry LimitedSource URLSource DetailFT-0603644Source Record URL
251911896AvaChem ScientificSource URLSource Detail1405Source Record URL
251914974AvaChem ScientificSource URLSource Detail3681-93-4Source Record URL
316469755abcr GmbHSource URLSource DetailAB253938Source Record URL
162187562AK Scientific, Inc. (AKSCI)Source URLSource DetailV0191Source Record URL
223668824AN PharmaTechSource URLSource DetailAN-10375Source Record URL
113853262ABI ChemSource URLSource DetailAC1NQX0ZSource Record URL
373567957AmbinterSource URLSource DetailAmb22168295Source Record URL
310281727Glentham Life Sciences Ltd.Source URLSource DetailGC5761Source Record URL
165235243ACT ChemicalSource URLSource DetailACT02625Source Record URL
126618213ChemMolSource URLSource Detail30112354Source Record URL
126662432ChemMolSource URLSource Detail49404664Source Record URL
318265992Chem-Space.com DatabaseSource URLSource DetailCSC000049362Source Record URL
374092532Combi-BlocksSource URLSource DetailQV-2656Source Record URL
274951902ChemFacesSource URLSource DetailCFN98601Source Record URL
341837878OChemSource URLSource Detail7733Source Record URL
162224445Chembase.cnSource URLSource Detail130161Source Record URL
255345025BiosynthSource URLSource DetailQ-100437Source Record URL
3570707381717 CheMall CorporationSource URLSource DetailBG01721469Source Record URL
3590309691717 CheMall CorporationSource URLSource DetailBG03783422Source Record URL
318366703CambridgeChemSource URLSource DetailDB10048Source Record URL
91698152MolPortSource URLSource DetailMolPort-003-935-138Source Record URL
329978108Acorn PharmaTech Product ListSource URLSource DetailACN-035536Source Record URL
163125868ChemTikSource URLSource DetailCTK8F0956Source Record URL
204940267TractusSource URLSource DetailTR-035805Source Record URL
347247600LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN01327612Source Record URL
257201979ZINCSource URLSource DetailZINC4245684Source Record URL
349011802Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0529948Source Record URL
29204675R&D ChemicalsSource URLSource Detail1232Source Record URL
348354639AbMole BioscienceSource URLSource DetailM4548Source Record URL
310118447Aurora Fine Chemicals LLCSource URLSource DetailA17.890.730Source Record URL