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Natural Product (NP) Details

General Information of the NP (ID: NP1083)
Name
Vitexin
Synonyms
Vitexin; 3681-93-4; Apigenin 8-C-glucoside; Vitxein; UNII-9VP70K75OK; 9VP70K75OK; CHEBI:16954; MFCD00017456; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-8-beta-D-glucopyranosyl-2-(4-hydroxyphenyl)-; 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one; Flavone, 8-D-glucosyl-4',5,7-trihydroxy-; (1S)-1,5-anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-D-glucitol; 8-beta-D-Glucopyranosyl-apigenin; EINECS 222-963-8; Vitexin,(S); Vitexin, analytical standard; 8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; SCHEMBL25277; CHEMBL487417; DTXSID90190287; 4H-1-Benzopyran-4-one, 8-.beta.-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-; Apigenin 8-C-.beta.-D-glucoside; ACT02625; HY-N0013; ZINC4245684; BDBM50362886; s9192; AKOS025311479; AC-6086; CCG-208516; 4H-1-Benzopyran-4-one, 8-beta-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-; NCGC00163642-01; 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one; AS-55909; (hydroxymethyl)tetrahydro-2H-pyran-2-yl)-; CS-0007090; N1319; V0191; A12135; C01460; 681V934; Q259075; Vitexin, primary pharmaceutical reference standard; Q-100437; 8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-; 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)-; 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one
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Species Origin Theaceae ...     Click to Show/Hide
Theaceae
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Ericales
Family: Theaceae
Disease Renal cell carcinoma [ICD-11: 2C90] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C21H20O10
PubChem CID
5280441
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
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
InChIKey
SGEWCQFRYRRZDC-VPRICQMDSA-N
CAS Number
CAS 3681-93-4
ChEBI ID
CHEBI:16954
Herb ID
HBIN048102
SymMap ID
SMIT00218
TCMSP ID
MOL004925
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Resistance can be Reversed by This NP
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression FOXO3  Molecule Info 
Pathway MAP
Down-regulation Expression IL6  Molecule Info 
Pathway MAP
Down-regulation Expression p105  Molecule Info 
Pathway MAP
                    In-vivo Model Model rats were induced by i.p. injection of DOX (2 mg/kg) once a week for 4 weeks.
                    Experimental
                    Result(s)
Vitexin possesses cardioprotective action against DOX-induced cardiotoxicity by suppressing oxidative stress, inflammation and apoptotic signals.
Target and Pathway
Target(s) Aquaporin-4 (SLC12A2)  Molecule Info  [3]
Arylamine N-acetyltransferase 1 (TJP1)  Molecule Info  [3]
References
Reference 1 Vitexin suppresses renal cell carcinoma by regulating mTOR pathways. Transl Androl Urol. 2020 Aug;9(4):1700-1711.
Reference 2 Vitexin attenuates acute doxorubicin cardiotoxicity in rats via the suppression of oxidative stress, inflammation and apoptosis and the activation of FOXO3a. Exp Ther Med. 2016 Sep;12(3):1879-1884.
Reference 3 Vitexin reduces epilepsy after hypoxic ischemia in the neonatal brain via inhibition of NKCC1. J Neuroinflammation. 2018 Jun 20;15(1):186.
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Cite NPCDR
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China