Natural Product (NP) Details

General Information of the NP (ID: NP0944)
Name
Ferulic acid
Synonyms
ferulic acid; trans-Ferulic Acid; 1135-24-6; 537-98-4; 4-Hydroxy-3-methoxycinnamic acid; trans-4-Hydroxy-3-methoxycinnamic acid; 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid; ferulate; (E)-Ferulic acid; Coniferic acid; 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-; 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid; Ferulic acid, trans-; Fumalic acid; (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid; Cinnamic acid, 4-hydroxy-3-methoxy-; 3-methoxy-4-hydroxycinnamic acid; (E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid; MFCD00004400; UNII-AVM951ZWST; Cinnamic acid, 4-hydroxy-3-methoxy-, (E)-; (E)-4-Hydroxy-3-methoxycinnamic acid; (E)-4'-Hydroxy-3'-methoxycinnamic acid; (2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid; 4-Hydroxy-3-methoxy cinnamic acid; Cinnamic acid, 4-hydroxy-3-methoxy-, trans-; 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, (2E)-; AVM951ZWST; (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid; (2E)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acid; Ferulic acid dehydrogenation homopolymer; (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid; Fumalic acid (Ferulic acid); 4-Hydroxy-3-methoxycinnamate; CHEMBL32749; 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, (E)-; 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid homopolymer; CHEBI:17620; NSC2821; 3-Methoxy-4-hydroxy-trans-cinnamate; 4-Hydroxy-3-Methoxycinnamic Acid, 99%; (E)-Ferulate; 3-(4-Hydroxy-3-methoxyphenyl)propenoic acid; 97274-61-8; CINNAMIC ACID,4-HYDROXY,3-METHOXY FERULIC ACID; caffeic acid 3-methyl ether; 3-methoxy-4-hydroxy-trans-cinnamic acid; SMR000112202; 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid; EINECS 208-679-7; ferulic acid (trans-4-hydroxy-3-methoxycinnamic acid); ferulasaure; trans-Ferulate; (E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate; CCRIS 3256; CCRIS 7127; CCRIS 7575; HSDB 7663; NSC 2821; Ferulic acid, E-; EINECS 214-490-0; NSC 51986; trans-4-Hydroxy-3-methoxycinnamicacid; Ferulic acid (M5); NSC 674320; PubChem8183; 3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid; Ferulic Acid ,(S); FERULIC-ACID; Ferulic Acid, Synthetic; Spectrum5_000554; bmse000459; bmse000587; bmse010211; trans-Ferulic acid, 99%; SCHEMBL15673; BSPBio_003168; MLS001066385; MLS001332483; MLS001332484; MLS002207079; MLS006011435; SPECTRUM1501017; trans-Ferulic acid, >=99%; (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoic acid; ZINC58258; DTXSID70892035; HMS1921D05; HMS2269P04; (E)-4-Hydroxy-3-methoxycinnamate; trans-4-Hydroxy-3-methoxycinnamate; ALBB-013505; BCP21231; BCP21789; HY-N0060; NSC-2821; NSC51986; STR00961; (E)-4-hydroxy-3-methoxy-Cinnamate; (E)4-hydroxy-3-methoxycinnamic acid; BBL010345; BDBM50214744; CCG-38860; CF0041; NSC-51986; s2300; SBB000326; STK801551; AKOS000263735; AC-7965; ACN-035275; BCP9000163; DB07767; PS-3435; SDCCGMLS-0066667.P001; trans-3-methoxy-4-hydroxycinnamic acid; (E)-4-hydroxy-3-methoxy-Cinnamic acid; 3-(4-Hydroxy-3-methoxyphenyl)propenoate; 4-Hydroxy-3-methoxycinnamic acid, trans; NCGC00094889-01; NCGC00094889-02; NCGC00094889-03; NCGC00094889-04; AC-10321; BS-17543; SMR004703246; ST097625; AM20060784; CS-0007108; N1878; SW219616-1; trans-Ferulic Acid (purified by sublimation); C01494; J10038; J10187; W-2799; ferulic acid (4-hydroxy-3-methoxycinnamic acid); A829775; Q417362; SR-01000765539; (2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate; J-002980; SR-01000765539-3; (E)-3-(3-methoxy-4-oxidanyl-phenyl)prop-2-enoic acid; 3-(4-HYDROXY-3-METHOXYPHENYL)PROP-2-ENOICACID; 055E203F-B305-4B7F-8CE7-F9C0C03AB609; 3986A1BE-A670-4B06-833B-E17253079FD8; Ferulic acid, European Pharmacopoeia (EP) Reference Standard; trans-Ferulic acid, certified reference material, TraceCERT(R); 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, (E)- (9CI); Diethyl2-(acetamido)-2-(2-(bromomethyl)-5-nitrobenzyl)malonate; Ferulic acid, United States Pharmacopeia (USP) Reference Standard; trans-Ferulic acid, matrix substance for MALDI-MS, >=99.0% (HPLC); 4-Hydroxy-3-methoxycinnamic acid, mixture of isomers, analytical reference material; Ferulic Acid, Pharmaceutical Secondary Standard; Certified Reference Material; 831-85-6
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Species Origin Ferula sinkiangensisK ...     Click to Show/Hide
Ferula sinkiangensisK
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Apiales
Family: Apiaceae
Genus: Ferula
Species: Ferula sinkiangensisK
Chinese chive seed extract (Allium tuberosum)
SuperKingdom: Eukaryota
Kingdom: Plantae
Phylum: Tracheophyta
Class: Liliopsida
Order: Asparagales
Family: Amaryllidaceae
Genus: Allium
Species: A. tuberosum
Disease Cervical cancer [ICD-11: 2C77] Investigative [1]
Staphylococcus aureus [ICD-11: XN6BM] Investigative
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.989
 
MDCK Permeability
 -4.791
 
PAMPA
 +
 
HIA
 - -
 
Distribution
VDss
 -0.727
 
PPB
 68.6%
 
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
 8.359
 
T1/2
 1.698
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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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C10H10O4
PubChem CID
445858
Canonical SMILES
COC1=C(C=CC(=C1)C=CC(=O)O)O
InChI
1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
InChIKey
KSEBMYQBYZTDHS-HWKANZROSA-N
CAS Number
CAS 537-98-4
ChEBI ID
CHEBI:17620
Herb ID
HBIN026465
SymMap ID
SMIT01860
TCMSP ID
MOL002665
TTD Drug ID
D03SLR
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Insulin      Acute diabete complication     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 BAX  Molecule Info 
Pathway MAP
Down-regulation Activity COX-2  Molecule Info 
Pathway MAP
                    In-vivo Model Overnight fasted rats (Adult male Sprague-Dawley rats) were injected intra-peritoneally with strepto zotocin (55 mg/kg) dissolved in citrate buffer (pH 4.5, 0.1 M) to induce diabetes.
                    Experimental
                    Result(s)		 Diabetic rats treated with insulin-FA combination demonstrated more pronounced beneficial effects as compared to either agent alone.
          Atorvastatin      Cardiovascular 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 [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression IL6  Molecule Info 
Pathway MAP
Down-regulation Expression TNF  Molecule Info 
Pathway MAP
                    In-vivo Model Male Swiss albino mice were given a diet containing high fat.
                    Experimental
                    Result(s)		 Simultaneous treatment with AS, F and their combination protected against HFD induced weight gain and oxidative stress.
          2-methoxyestradiol      Pulmonary hypertension     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
                    Molecule(s)
                    Regulation		 Down-regulation Expression HSPD1  Molecule Info 
Pathway MAP
                    In-vitro Model A-375 CVCL_0132 Amelanotic melanoma Homo sapiens
                    Experimental
                    Result(s)		 2-Methoxyestradiol and its combination with ferulic acid induces melanoma cell death via downregulation of Hsp60 and Hsp90.
          ABT-888      Malignant mesenchymal neoplasm     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 [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
U2OS CVCL_0042 Osteosarcoma Homo sapiens
                    Experimental
                    Result(s)		 Ferulic acid in combination with PARP inhibitor sensitizes breast cancer cells as chemotherapeutic strategy.
Target and Pathway
Target(s) Carbonic anhydrase (CA)  Molecule Info  [6]
Monoamine oxidase B (MAO-B)  Molecule Info  [7]
BioCyc Superpathway of tryptophan utilization Click to Show/Hide
2 Tryptophan degradation via tryptamine
3 Dopamine degradation
4 Putrescine degradation III
5 Noradrenaline and adrenaline degradation
KEGG Pathway Glycine, serine and threonine metabolism Click to Show/Hide
2 Arginine and proline metabolism
3 Histidine metabolism
4 Tyrosine metabolism
5 Phenylalanine metabolism
6 Tryptophan metabolism
7 Drug metabolism - cytochrome P450
8 Metabolic pathways
9 Serotonergic synapse
10 Dopaminergic synapse
11 Cocaine addiction
12 Amphetamine addiction
13 Alcoholism
Panther Pathway Adrenaline and noradrenaline biosynthesis Click to Show/Hide
2 5-Hydroxytryptamine degredation
3 Dopamine receptor mediated signaling pathway
Pathway Interaction Database Alpha-synuclein signaling Click to Show/Hide
WikiPathways Tryptophan metabolism Click to Show/Hide
2 Dopamine metabolism
3 Phase 1 - Functionalization of compounds
References
Reference 1 Ferulic Acid Induces Apoptosis of HeLa and Caski Cervical Carcinoma Cells by Down-Regulating the Phosphatidylinositol 3-Kinase (PI3K)/Akt Signaling Pathway. Med Sci Monit. 2020 Jan 27;26:e920095.
Reference 2 Beneficial effects of ferulic acid alone and in combination with insulin in streptozotocin induced diabetic neuropathy in Sprague Dawley rats. Life Sci. 2020 Aug 15;255:117856.
Reference 3 Promising role of ferulic acid, atorvastatin and their combination in ameliorating high fat diet-induced stress in mice. Life Sci. 2013 May 20;92(17-19):938-49.
Reference 4 2-Methoxyestradiol and Its Combination with a Natural Compound, Ferulic Acid, Induces Melanoma Cell Death via Downregulation of Hsp60 and Hsp90. J Oncol. 2019 Oct 2;2019:9293416.
Reference 5 Ferulic acid in combination with PARP inhibitor sensitizes breast cancer cells as chemotherapeutic strategy. Biochem Biophys Res Commun. 2015 Mar 13;458(3):520-524.
Reference 6 Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-2164.
Reference 7 Novel monoamine oxidase inhibitors: a patent review (2012 - 2014).Expert Opin Ther Pat. 2015 Jan;25(1):91-110.
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