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

ADMET Property
Absporption
Caco-2 Permeability
 -6.278
 
MDCK Permeability
 -5.017
 
PAMPA
 +++
 
HIA
 -
 
Distribution
VDss
 -0.011
 
PPB
 85.6%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 +
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 - - -
 
Excretion
CLplasma
 3.534
 
T1/2
 4.404
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 - - -
 
FDAMDD
 - -
 
Respiratory
 - -
 
Human Hepatotoxicity
 +
 
Ototoxicity
 +
 
Drug-induced Nephrotoxicity
 - -
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - - -
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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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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