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Natural Product (NP) Details

General Information of the NP (ID: NP6152)
Name
Apocynin
Synonyms
Acetovanillone; apocynin; 498-02-2; 4'-Hydroxy-3'-methoxyacetophenone; 1-(4-Hydroxy-3-methoxyphenyl)ethanone; Acetoguaiacone; Apocynine; Acetoguaiacon; 4-Acetyl-2-methoxyphenol; Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-; Acetovanilone; Acetovanyllon; 3-Methoxy-4-hydroxyacetophenone; Acetovanillon; 4-HYDROXY-3-METHOXYACETOPHENONE; 4-Hydroxy-3-methoxyphenyl methyl ketone; 1-(4-hydroxy-3-methoxyphenyl)ethan-1-one; Acetophenone, 4'-hydroxy-3'-methoxy-; NSC 209524; UNII-B6J7B9UDTR; EINECS 207-854-5; BRN 0637373; 3-Metoksy-4-hydroksyacetofenon; 2-methoxy-4-acetylphenol; B6J7B9UDTR; CHEBI:2781; MFCD00008747; NSC-209524; Acetovanillone, 98%; 1-(4-hydroxy-3-methoxy-phenyl)-ethanone; WLN: 1VR DQ CO1; 1-acetyl-4-hydroxy-3-methoxybenzene; CCRIS 7285; 3-Metoksy-4-hydroksyacetofenon [Polish]; AI3-15892; 4-Acetylguaiacol; PubChem3315; Vanilloyl methyl ketone; 1-(4-hydroxy-3-methoxy-phenyl)ethanone; ACMC-1AHLR; apocynin (acetovanillone); bmse000584; bmse010031; AURORA KA-3667; Phenol, 4-acetyl-2-methoxy; 4-08-00-01814 (Beilstein Handbook Reference); MLS001304972; SCHEMBL109514; 4-hydroxy3-methoxyacetophenone; 4hydroxy-3-methoxyacetophenone; Acetovanillone, >=98%, FG; CHEMBL346919; DTXSID7060097; TIMTEC-BB SBB008060; 4-hydroxy -3-methoxyacetophenone; NSC2146; Acetovanillone, analytical standard; HMS3651H03; ZINC162515; 3'-Methoxy-4'-hydroxyacetophenone; HY-N0088; NSC-2146; STR03975; AKOS BBS-00003229; ANW-30844; BBL009710; NSC209524; s2425; SBB008060; STL141075; ZINC00162515; AKOS000120562; 4-Hydroxy-3-methoxyphenyl methyl keton; AS03910; CCG-266327; CM10957; CS-5647; DB12618; FS-3673; MCULE-4549346345; 1-(4-hydroxy-3-methoxyphenyl)-ethanone; NCGC00247065-01; 4'-Hydroxy-3'-methoxyacetophenone, 98%; AC-29981; AK-42915; L911; SMR000752909; 1-(4-Hydroxy-3-methoxyphenyl)-1-ethanone; AM20090774; FT-0618638; ST50213415; SW219526-1; A11989; C11380; M-6166; 21432-EP2311824A1; 21432-EP2314295A1; AA-504/20839006; Q414754; Q-200477; ACETOPHENONE,4-HYDROXY,3-METHOXY ACETOVANILLON; F2191-0004; 4 inverted exclamation marka-Hydroxy-3 inverted exclamation marka-methoxyacetophenone; 16522-48-8; I75
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Species Origin Picrorhiza kurrooa ...     Click to Show/Hide
Picrorhiza kurrooa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Plantaginaceae
Genus: Picrorhiza
Species: Picrorhiza kurrooa
Disease Asthma [ICD-11: CA23] Phase 1 [1]
Structure
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2D MOL

3D MOL

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Formula
C9H10O3
PubChem CID
2214
Canonical SMILES
CC(=O)C1=CC(=C(C=C1)O)OC
InChI
1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
InChIKey
DFYRUELUNQRZTB-UHFFFAOYSA-N
CAS Number
CAS 498-02-2
ChEBI ID
CHEBI:2781
Herb ID
HBIN016505
SymMap ID
SMIT04971
TCMSP ID
MOL002786
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Edaravone      Motor neuron disease     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     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
Up-regulation Expression AKT1  Molecule Info 
Pathway MAP
Up-regulation Expression GABPA  Molecule Info 
Pathway MAP
Up-regulation Expression mTOR  Molecule Info 
Pathway MAP
Up-regulation Expression PIK3CB  Molecule Info 
Pathway MAP
                    In-vivo Model Male Wistar rats weighing 180-210 g were used in this study.
                    Experimental
                    Result(s)
AV and ED prevent CP cardiotoxicity by attenuating oxidative stress and tissue injury, and modulating cytoglobin, and PI3K/Akt/mTOR and Keap1/Nrf2 signaling.
          Captopril + Losartan     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model A 5/6 nephrectomy mouse model of CDK was used in this study.
                    Experimental
                    Result(s)
Apocynin in conjunction with a coadjuvant for modulating blood pressure may be useful for controlling the progression of CRF.
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Cyclophosphamide      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression AKT1  Molecule Info 
Pathway MAP
Up-regulation Expression GABPA  Molecule Info 
Pathway MAP
Up-regulation Expression GCLC  Molecule Info 
Pathway MAP
Up-regulation Expression HMOX1  Molecule Info 
Pathway MAP
Down-regulation Expression KEAP1  Molecule Info 
Pathway MAP
Up-regulation Expression mTOR  Molecule Info 
Pathway MAP
Up-regulation Expression PIK3CB  Molecule Info 
Pathway MAP
Up-regulation Expression SOD3  Molecule Info 
Pathway MAP
                    In-vivo Model Male Wistar rats weighing 180-210 g were used in this study.
                    Experimental
                    Result(s)
Acetovanillone prevents cyclophosphamide-induced acute lung injury by modulating PI3K/Akt/mTOR and Nrf2 signaling in rats.
References
Reference 1 ClinicalTrials.gov (NCT00992667) Inhaled Apocynin Decreases Reactive Oxygen Species Concentrations in Exhaled Breath Condensate in Mild Asthmatics
Reference 2 Edaravone and Acetovanillone Upregulate Nrf2 and PI3K/Akt/mTOR Signaling and Prevent Cyclophosphamide Cardiotoxicity in Rats. Drug Des Devel Ther. 2020 Nov 30;14:5275-5288.
Reference 3 Acetovanillone prevents cyclophosphamide-induced acute lung injury by modulating PI3K/Akt/mTOR and Nrf2 signaling in rats. Phytother Res. 2021 May 9.
Reference 4 Apocynin combined with drugs as coadjuvant could be employed to prevent and/or treat the chronic kidney disease. Ren Fail. 2018 Nov;40(1):92-98.
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Cite NPCDR
Visitor Map
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