Details of Metabolite

General Information of MET (ID: META00799)
Name Isoferulic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid; (2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoate; (e)-3-Hydroxy-4-methoxycinnamic acid; (e)-4-Methoxycaffeic acid; (e)-4-O-Methylcaffeic acid; (e)-Hesperetic acid; (e)-Isoferulic acid; 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoate; 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid; 3-Hydroxy-4-methoxy-cinnamate; 3-Hydroxy-4-methoxy-cinnamic acid; 3-Hydroxy-4-methoxycinnamate; 3-Hydroxy-4-methoxycinnamic acid; 4-Methoxycaffeic acid; 4-O-Methylcaffeic acid; Hesperetate; Hesperetic acid; Isoferulate; Isoferulic acid; trans-3-Hydroxy-4-methoxycinnamic acid; trans-4-Methoxycaffeic acid; trans-4-O-Methylcaffeic acid; trans-Hesperetic acid; trans-Isoferulic acid
Source Food;Plant;Metabolite;Food;Drug;TCM Ingredients;Plant Metabolite
Structure Type   Hydroxycinnamic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Phenylpropanoids and polyketides
Cinnamic acids and derivatives
Hydroxycinnamic acids and derivatives
PubChem CID
736186
HMDB ID
HMDB0000955
Formula
C10H10O4
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C10470
DrugBank ID
DB07109
ChEBI ID
27794
FooDB ID
FDB002700
ChemSpider ID
643318
METLIN ID
5901
Physicochemical Properties Molecular Weight 194.18 Topological Polar Surface Area 66.8
XlogP 1.5 Complexity 224
Heavy Atom Count 14 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Function
Isoferulic acid (CAS: 537-73-5) is a chlorogenic acid (CGA). CGAs are formed by the esterification of hydroxycinnamic acids (e.g. caffeic acid, ferulic acid, and p-coumaric acid) with quinic acid. CGAs are abundant phenolic compounds in coffee, with caffeoylquinic (CQA), feruloylquinic (FQA), and dicaffeoylquinic (diCQA) acids being the major subclasses, and coffee is the most consumed food product in the world. Isoferulic acid is present in normal human urine in concentrations of 0.05-2.07 umol/mmol creatinine at baseline, and reaches 0.2-9.6 umol/mmol creatinine in four hours after a cup of coffee, with a large inter-individual variation.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transcription factor (TF)
            R2R3-MYB (AN2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of AN2
                      Induced Change Isoferulic acid concentration: increase (FC = 4.40)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the increase of isoferulic acid levels compared with control group.
References
1 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.

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