Details of Metabolite

General Information of MET (ID: META00843)
Name Rosmarinic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactate; (2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactic acid; (R)-Rosmarinate; Labiatenic acid; Labiatic acid; Rosemaric acid; Rosemary acid; Rosmarinate; Rosmarinic acid; Rosmarinic acid, (R-(e))-isomer; trans-Rosmarinic acid
Source Endogenous;Food
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
5281792
HMDB ID
HMDB0003572
Formula
C18H16O8
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
C01850
ChEBI ID
50371
FooDB ID
FDB002427
ChemSpider ID
4445104
METLIN ID
6960
Physicochemical Properties Molecular Weight 360.3 Topological Polar Surface Area 145
XlogP 2.4 Complexity 519
Heavy Atom Count 26 Rotatable Bond Count 7
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 8
Function
Rosmarinic acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid. It is commonly found in species of the Boraginaceae and the subfamily Nepetoideae of the Lamiaceae. It is a red-orange powder that is slightly soluble in water, but well soluble is most organic solvents. Rosmarinic acid is one of the polyphenolic substances contained in culinary herbs such as perilla (Perilla frutescens L.), rosemary (Rosmarinus officinalis L.), sage (Salvia officinalis L.), mint (Mentha arvense L.), and basil (Ocimum basilicum L.). These herbs are commonly grown in the garden as kitchen herbs, and while used to add flavor in cooking, are also known to have several potent physiological effects. BioTransformer predicts that rosmarinic acid is a product of methylrosmarinic acid metabolism via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction occurring in humans and human gut microbiota and catalyzed by the liver carboxylesterase 1 (P23141) enzyme.
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 Rosmarinic acid concentration: decrease (FC = 0.49)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the decrease of rosmarinic 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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