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Natural Product (NP) Details

General Information of the NP (ID: NP6356)
Name
Vanillic acid
Synonyms
Vanillic acid; 4-HYDROXY-3-METHOXYBENZOIC ACID; 121-34-6; Acide vanillique; Benzoic acid, 4-hydroxy-3-methoxy-; p-Vanillic acid; 3-Methoxy-4-hydroxybenzoic acid; Vanillate; m-Anisic acid, 4-hydroxy-; Protocatechuic acid, 3-methyl ester; 4-hydroxy-3-methoxy-Benzoic acid; UNII-GM8Q3JM2Y8; 4-Hydroxy-3-methoxybenzoate; NSC 3987; MFCD00002551; NSC 674322; GM8Q3JM2Y8; CHEMBL120568; CHEBI:30816; 4-hydroxy-3-methoxy benzoic acid; NSC674322; VA; VA (VAN); 4-Hydroxy-3-methoxybenzoic acid, 97+%; VNL; 4-hydroxy-m-Anisic acid; EINECS 204-466-8; BRN 2208364; Vanillinsaure; p-Vanillate; Vanilic acid; AI3-19542; Vanillic Acid,(S); 4-hydroxy-m-Anisate; Vanillic acid (M2); Vanillic acid, 97%; PubChem19485; ACMC-1BPT2; bmse000486; bmse000614; bmse010205; WLN: QVR DQ CO1; 3-Methoxy-4-hydroxybenzoate; SCHEMBL26179; MLS000574833; 4-hydroxy-3-methoxy-Benzoate; 4-Hydroxy-3-methoxybenzoicacid; Vanillic acid, >=97%, FG; 4-hydroxy-3methoxy benzoic acid; DTXSID6059522; 4-hydroxyl-3-methoxybenzoic acid; NSC3987; 4- hydroxy-3-methoxybenzoic acid; HMS2197E16; Protocatechuic acid 3-methyl ester; ZINC338275; HY-N0708; NSC-3987; STR02334; ANW-17590; BBL011982; BDBM50337364; s5343; SBB008280; STL163472; AKOS000113195; CCG-266343; MCULE-2667517874; MP-2220; NSC-674322; NCGC00247610-01; AC-11841; AK-32998; BP-13246; SMR000156289; ST086485; SY001450; DB-003804; Vanillic acid, purum, >=97.0% (HPLC); AM20050239; CS-0009728; FT-0650155; C06672; Vanillic acid, Vetec(TM) reagent grade, 97%; 198598-EP2277877A1; Q419672; Q-201921; Z1741973874; Vanillic acid, certified reference material, TraceCERT(R); 3E9555E5-85F5-4FCE-A429-5182E959C6A3
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Species Origin Angelica sinensis ...     Click to Show/Hide
Angelica sinensis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Apiales
Family: Apiaceae
Genus: Angelica
Species: Angelica sinensis
Disease Asthma [ICD-11: CA23] Investigative [1]
Structure
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2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C8H8O4
PubChem CID
8468
Canonical SMILES
COC1=C(C=CC(=C1)C(=O)O)O
InChI
1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
InChIKey
WKOLLVMJNQIZCI-UHFFFAOYSA-N
CAS Number
CAS 121-34-6
ChEBI ID
CHEBI:30816
Herb ID
HBIN047738
SymMap ID
SMIT00015
TCMSP ID
MOL000114
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Doxorubicin      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 [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression TLR4  Molecule Info 
Pathway MAP
                    In-vivo Model Male Wistar albino rats weighing 200 +/- 20 g were used in this study.
                    Experimental
                    Result(s)
VA exerts cardioprotective effects against DOX-induced cardiotoxicity by decreasing oxidative stress and biomarkers of cardiotoxicity, suppression of TLR4 signaling and consequently inflammation pathway.
Target and Pathway
Target(s) CCAAT/enhancer-binding alpha (CEBPA)  Molecule Info  [3]
PPAR-gamma (PPARG)  Molecule Info  [3]
KEGG Pathway PPAR signaling pathway Click to Show/Hide
2 AMPK signaling pathway
3 Osteoclast differentiation
4 Huntington's disease
5 Pathways in cancer
6 Transcriptional misregulation in cancer
7 Thyroid cancer
NetPath Pathway IL1 Signaling Pathway Click to Show/Hide
2 TGF_beta_Receptor Signaling Pathway
3 Leptin Signaling Pathway
Panther Pathway CCKR signaling map ST Click to Show/Hide
Pathway Interaction Database Noncanonical Wnt signaling pathway Click to Show/Hide
2 Calcineurin-regulated NFAT-dependent transcription in lymphocytes
3 Signaling events mediated by HDAC Class I
4 RXR and RAR heterodimerization with other nuclear receptor
5 Regulation of retinoblastoma protein
Reactome PPARA activates gene expression Click to Show/Hide
2 Transcriptional regulation of white adipocyte differentiation
3 Nuclear Receptor transcription pathway
WikiPathways Wnt Signaling Pathway Netpath Click to Show/Hide
2 Nuclear Receptors in Lipid Metabolism and Toxicity
3 Differentiation of white and brown adipocyte
4 Regulation of Lipid Metabolism by Peroxisome proliferator-activated receptor alpha (PPARalpha)
5 Transcriptional Regulation of White Adipocyte Differentiation
6 Adipogenesis
7 SREBP signalling
8 Nuclear Receptors
References
Reference 1 Vanillic acid mitigates the ovalbumin (OVA)-induced asthma in rat model through prevention of airway inflammation. Biosci Biotechnol Biochem. 2019 Mar;83(3):531-537.
Reference 2 Cardioprotective effect of vanillic acid against doxorubicin-induced cardiotoxicity in rat. Res Pharm Sci. 2020 Feb 20;15(1):87-96.
Reference 3 Vanillic acid attenuates obesity via activation of the AMPK pathway and thermogenic factors in vivo and in vitro. FASEB J. 2018 Mar;32(3):1388-1402.
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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