MiMeDB: Showing metabocard for Ferulic acid (MMDBc0000174)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:38:35 UTC

Update Date

2024-10-09 22:30:56 UTC

Metabolite ID

MMDBc0000174

Metabolite Identification

Common Name

Ferulic acid

Description

Ferulic acid is a highly abundant phenolic phytochemical which is present in plant cell walls. Ferulic acid is a phenolic acid that can be absorbed by the small intestine and excreted through the urine. It is one of the most abundant phenolic acids in plants, varying from 5 g/kg in wheat bran to 9 g/kg in sugar-beet pulp and 50 g/kg in corn kernel. It occurs primarily in seeds and leaves both in its free form (albeit rarely) and covalently linked to lignin and other biopolymers. It is usually found as ester cross-links with polysaccharides in the cell wall, such as arabinoxylans in grasses, pectin in spinach and sugar beet, and xyloglucans in bamboo. It also can cross-link with proteins. Due to its phenolic nucleus and an extended side chain conjugation (carbohydrates and proteins), it readily forms a resonance-stabilized phenoxy radical which accounts for its potent antioxidant potential. Food supplementation with curcumin and ferulic acid is considered a nutritional approach to reducing oxidative damage and amyloid pathology in Alzheimer disease (PMID: 17127365 , 1398220 , 15453708 , 9878519 ). Ferulic acid can be found in Pseudomonas and Saccharomyces (PMID: 8395165 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309272007352D          

 14 14  0  0  0  0            999 V2000
10000.732310000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4470 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.161810000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8766 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.161810001.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.878910000.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1633 9999.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8789 9998.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.021210000.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.306710000.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.592210000.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5922 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3066 9998.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0212 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  1  9  1  0  0  0  0
 11  6  1  0  0  0  0
 12  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000174

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=C(O)C=CC(\C=C\C(O)=O)=C1

> <INCHI_IDENTIFIER>
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+

> <INCHI_KEY>
KSEBMYQBYZTDHS-HWKANZROSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.184

> <EXACT_MASS>
194.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.180103670792548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.6748496726666668

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.982312921511172

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7673485922827705

> <JCHEM_PKA_STRONGEST_BASIC>
-4.89396153310966

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
51.504000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ferulic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.0348667.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3688666.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.7028667.436   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8672.0368666.666   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8670.7028668.974   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8662.7078667.436   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8661.3718666.665   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8662.7078664.359   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8666.7068666.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.3738667.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.0398666.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.0398665.128   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3728664.358   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.7068665.128   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7   11                                                       
CONECT    7    6                                                            
CONECT    8   12                                                            
CONECT    9   10   14    1                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12    6                                                  
CONECT   12   11   13    8                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Value	Source
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid	ChEBI
(e)-4'-Hydroxy-3'-methoxycinnamic acid	ChEBI
(e)-4-Hydroxy-3-methoxycinnamic acid	ChEBI
(e)-Ferulic acid	ChEBI
3-(4-Hydroxy-3-methoxyphenyl)propenoic acid	ChEBI
3-Methoxy-4-hydroxy-trans-cinnamic acid	ChEBI
4-Hydroxy-3-methoxycinnamic acid	ChEBI
trans-4-Hydroxy-3-methoxycinnamic acid	ChEBI
3-Methoxy-4-hydroxy-trans-cinnamate	Kegg
4-Hydroxy-3-methoxycinnamate	Kegg
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate	Generator
(e)-4'-Hydroxy-3'-methoxycinnamate	Generator
(e)-4-Hydroxy-3-methoxycinnamate	Generator
(e)-Ferulate	Generator
3-(4-Hydroxy-3-methoxyphenyl)propenoate	Generator
trans-4-Hydroxy-3-methoxycinnamate	Generator
trans-Ferulate	Generator
Ferulate	Generator
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate	HMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid	HMDB
(e)-4-Hydroxy-3-methoxy-cinnamate	HMDB
(e)-4-Hydroxy-3-methoxy-cinnamic acid	HMDB
Ferulic acid, (e)-isomer	MeSH, HMDB
Ferulic acid, monosodium salt	MeSH, HMDB
Sodium ferulate	MeSH, HMDB
Ferulic acid, (Z)-isomer	MeSH, HMDB
8,8'-Diferulic acid	MeSH, HMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-acrylic acid	HMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid	HMDB
(E)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acid	HMDB
Fumalic acid	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid	HMDB
3-Methoxy-4-hydroxycinnamic acid	HMDB
4'-Hydroxy-3'-methoxycinnamic acid	HMDB
Coniferic acid	HMDB
Ferulaic acid	HMDB
4’-Hydroxy-3’-methoxycinnamic acid	PhytoBank

Molecular Formula

C₁₀H₁₀O₄

Average Mass

194.184

Monoisotopic Mass

194.057908808

IUPAC Name

(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

Traditional Name

ferulic acid

CAS Registry Number

537-98-4

SMILES

COC1=C(O)C=CC(\C=C\C(O)=O)=C1

InChI Identifier

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+

InChI Key

KSEBMYQBYZTDHS-HWKANZROSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ferulic acids (CHEBI:17620 )
Coniferyl alcohol derivatives (C01494 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.91 g/L	ALOGPS
logP	1.58	ALOGPS
logP	1.67	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.5 m³·mol⁻¹	ChemAxon
Polarizability	19.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Epidermis
Feces
Fibroblasts
Urine

Tissue Locations

Epidermis
Fibroblasts

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0197061	Sulfotransferase 1A3	Enzyme	P0DMM9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0020071	4-Vinylguaiacol	Ferulic acid	Ferulic acid decarboxylase 1	Carboxylation	PathBank	31602464
MMDBr0038850	Feruloyl-CoA	Ferulic acid	Thioesterase TesA	Hydrolysis	RHEA	34755880

Multistep Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source
MMDBr0012797	Ferulic acid	Vanillic acid	Not Available
MMDBr0012833	Ferulic acid	5-Hydroxyferulic acid	Not Available	KEGG
MMDBr0012834	5-Hydroxyferulic acid	Sinapic acid	Not Available	KEGG

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Eosinophilic esophagitis	Slight Increase	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Glucose uptake	increases	Cell culture	3T3-L1 adipocytes	PubMed	28230764
Glucose uptake	increases	Cell culture	Rat L6 myotubes	PubMed	28230764
Free radical scavenger		Chemical reaction		Pubchem	28415050

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Spirochaetes	1		Microbial culture
Bacteria/Eubacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Proteobacteria	3	Human feces; Human stool; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Firmicutes	5	Human stool; Human ; Human feces; Human urine; Human sputum; Human saliva; Human subgingival plaque; Human vaginal fluid; Human supragingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	nah	1
Bacteria	Proteobacteria	1	Human feces; Human stool; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	4	Human feces; Human saliva	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.039	0.02			uM	Adult (>18 years old)	Both	Normal	HMDB	11308321
Human Urine	Detected and Quantified	36.3	11.2			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12663291
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	18502705
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	19573517
Human Blood	Detected and Quantified	0.031	0.008			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.157	0.129			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.13	0.054			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.031	0.011			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.027	0.005			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.029	0.004			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.052	0.02			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.053	0.017			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified			0	1.581	uM	Adult (>18 years old)	Both	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.481	0.188			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.245	0.061			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.364	0.108			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Hypertension (mild)	HMDB	20013882
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Hypertension (mild)	HMDB	20013882
Human Urine	Detected and Quantified	0.5				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	21388201
Human Feces	Detected and Quantified	8.549	0.978			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	13.853	11.072			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	11.793	6.952			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	13.801	11.844			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Urine	Detected and Quantified	1				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	1.2				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal cancer	HMDB	25037050
Human Feces	Detected but not Quantified						Not Specified	Both	Normal	HMDB	25486321
Human Urine	Detected and Quantified			0.376	9.27	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Urine	Detected and Quantified			0.8	1.3	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.78	0.98	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal cancer	HMDB	27015276
Human Urine	Detected and Quantified	2.814				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal Cancer	HMDB	27275383
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected and Quantified	0.34		0.00515	5.021	nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	28029051
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Bladder cancer	HMDB	28157703
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected and Quantified	22.261				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	10.181	5.131			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	5.626	2.711			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	3.557	2.039			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	4.18	3.519			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	0.5				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	21388201
Human Urine	Detected and Quantified	1				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	1.2				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	2.814				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Blood	Detected and Quantified			0	1.581	uM	Adult (>18 years old)	Both	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.027	0.005			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.029	0.004			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.031	0.008			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.031	0.011			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.039	0.020			uM	Adult (>18 years old)	Both	Normal	HMDB	11308321
Human Blood	Detected and Quantified	0.052	0.02			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.053	0.017			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.13	0.054			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.157	0.129			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.245	0.061			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Feces	Detected and Quantified	0.340		0.00515	5.0210	nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	28029051
Human Urine	Detected and Quantified	0.364	0.108			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified			0.376	9.270	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Urine	Detected and Quantified	0.481	0.188			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified			0.78	0.98	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified			0.80	1.3	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Feces	Detected and Quantified	11.793	6.952			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	13.801	11.844			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	13.853	11.0720			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Urine	Detected and Quantified	36.3	11.2			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12663291
Human Feces	Detected and Quantified	8.549	0.978			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Urine	Detected and Quantified	10.181	5.131			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	4.18	3.519			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	3.557	2.039			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	5.626	2.711			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	19573517
Human Feces	Detected but not Quantified						Not Specified	Both	Normal	HMDB	25486321
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	18502705
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000954

DrugBank ID

DB07767

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Ferulic_Acid

METLIN ID

4156

PubChem Compound

445858

PDB ID

Not Available

ChEBI ID

17620

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Graf E: Antioxidant potential of ferulic acid. Free Radic Biol Med. 1992 Oct;13(4):435-48. doi: 10.1016/0891-5849(92)90184-i. [PubMed:1398220 ]
Schindler AE, Siiteri PK: Isolation and quantitation of steroids from normal human amniotic fluid. J Clin Endocrinol Metab. 1968 Aug;28(8):1189-98. doi: 10.1210/jcem-28-8-1189. [PubMed:4234060 ]
Huang Z, Dostal L, Rosazza JP: Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens. Appl Environ Microbiol. 1993 Jul;59(7):2244-50. doi: 10.1128/aem.59.7.2244-2250.1993. [PubMed:8395165 ]
Bourne LC, Rice-Evans C: Bioavailability of ferulic acid. Biochem Biophys Res Commun. 1998 Dec 18;253(2):222-7. doi: 10.1006/bbrc.1998.9681. [PubMed:9878519 ]
Choudhary G, Chakel J, Hancock W, Torres-Duarte A, McMahon G, Wainer I: Investigation of the potential of capillary electrophoresis with off-line matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for clinical analysis: examination of a glycoprotein factor associated with cancer cachexia. Anal Chem. 1999 Feb 15;71(4):855-9. doi: 10.1021/ac980633k. [PubMed:10051848 ]
Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. doi: 10.1248/bpb.23.122. [PubMed:10706426 ]
Tringali C, Spatafora C, Longo OD: Bioactive constituents of the bark of Parkia biglobosa. Fitoterapia. 2000 Apr;71(2):118-25. doi: 10.1016/s0367-326x(99)00137-9. [PubMed:10727806 ]
Saija A, Tomaino A, Trombetta D, De Pasquale A, Uccella N, Barbuzzi T, Paolino D, Bonina F: In vitro and in vivo evaluation of caffeic and ferulic acids as topical photoprotective agents. Int J Pharm. 2000 Apr 10;199(1):39-47. doi: 10.1016/s0378-5173(00)00358-6. [PubMed:10794925 ]
Homma K, Hasegawa T, Masumoto M, Takeshita E, Watanabe K, Chiba H, Kurosawa T, Takahashi T, Matsuo N: Reference values for urinary steroids in Japanese newborn infants: gas chromatography/mass spectrometry in selected ion monitoring. Endocr J. 2003 Dec;50(6):783-92. doi: 10.1507/endocrj.50.783. [PubMed:14709852 ]
Trombino S, Serini S, Di Nicuolo F, Celleno L, Ando S, Picci N, Calviello G, Palozza P: Antioxidant effect of ferulic acid in isolated membranes and intact cells: synergistic interactions with alpha-tocopherol, beta-carotene, and ascorbic acid. J Agric Food Chem. 2004 Apr 21;52(8):2411-20. doi: 10.1021/jf0303924. [PubMed:15080655 ]
Harder H, Tetens I, Let MB, Meyer AS: Rye bran bread intake elevates urinary excretion of ferulic acid in humans, but does not affect the susceptibility of LDL to oxidation ex vivo. Eur J Nutr. 2004 Aug;43(4):230-6. doi: 10.1007/s00394-004-0463-5. Epub 2004 Jan 6. [PubMed:15309442 ]
Baba S, Osakabe N, Natsume M, Yasuda A, Muto Y, Hiyoshi K, Takano H, Yoshikawa T, Terao J: Absorption, metabolism, degradation and urinary excretion of rosmarinic acid after intake of Perilla frutescens extract in humans. Eur J Nutr. 2005 Feb;44(1):1-9. doi: 10.1007/s00394-004-0482-2. Epub 2004 Feb 18. [PubMed:15309457 ]
Kang J, Liu Y, Xie MX, Li S, Jiang M, Wang YD: Interactions of human serum albumin with chlorogenic acid and ferulic acid. Biochim Biophys Acta. 2004 Sep 24;1674(2):205-14. doi: 10.1016/j.bbagen.2004.06.021. [PubMed:15374625 ]
Fukuoka K, Sawabe A, Sugimoto T, Koga M, Okuda H, Kitayama T, Shirai M, Komai K, Komemushi S, Matsuda K: Inhibitory actions of several natural products on proliferation of rat vascular smooth muscle cells induced by Hsp60 from Chlamydia pneumoniae J138. J Agric Food Chem. 2004 Oct 6;52(20):6326-9. doi: 10.1021/jf0351164. [PubMed:15453708 ]
Tapia A, Rodriguez J, Theoduloz C, Lopez S, Feresin GE, Schmeda-Hirschmann G: Free radical scavengers and antioxidants from Baccharis grisebachii. J Ethnopharmacol. 2004 Dec;95(2-3):155-61. doi: 10.1016/j.jep.2004.06.035. [PubMed:15507329 ]
Mancuso C, Scapagini G, Curro D, Giuffrida Stella AM, De Marco C, Butterfield DA, Calabrese V: Mitochondrial dysfunction, free radical generation and cellular stress response in neurodegenerative disorders. Front Biosci. 2007 Jan 1;12:1107-23. doi: 10.2741/2130. [PubMed:17127365 ]

Showing metabocard for Ferulic acid (MMDBc0000174)

MOL for #<Metabolite:0x00007f922838f498>

3D MOL for #<Metabolite:0x00007f922838f498>

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Structure for #<Metabolite:0x00007f922838f498>

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