Jump To Section:

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2015-01-30 22:04:27 UTC

Update Date

2023-02-21 17:30:38 UTC

HMDB ID

HMDB0062121

Secondary Accession Numbers

HMDB62121

Metabolite Identification

Common Name

Dihydroferulic acid

Description

Dihydroferulic acid, also known as 3-(4-hydroxy-3-methoxyphenyl)propionic acid or dihydroconiferylate, is classified as a member of the phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Dihydroferulic acid is considered to be slightly soluble (in water) and acidic. Dihydroferulic acid is a phenolic acid metabolite and was found to be significantly elevated in serum after whole grain consumption which makes this compound a potential serum biomarker of whole grain intake (PMID: 25646321 ).

Structure

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

  Mrv1652309272007472D          

 14 14  0  0  0  0            999 V2000
10017.751910017.8102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.611110019.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.325110019.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.041210019.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.755310019.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10022.041210020.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.896910019.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.182510019.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.467910019.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.467910018.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.182310017.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.896910018.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.182210016.9835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.898110016.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  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  7  1  0  0  0  0
  1 10  1  0  0  0  0
  7  2  1  0  0  0  0
  2  3  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062121

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CCC(O)=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)

> <INCHI_KEY>
BOLQJTPHPSDZHR-UHFFFAOYSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.1999

> <EXACT_MASS>
196.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.802083951346205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxy-3-methoxyphenyl)propanoic acid

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.5943261829999997

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.946560494761734

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9524008986487043

> <JCHEM_PKA_STRONGEST_BASIC>
-4.892121858205717

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
50.410700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
homovanillinic 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  O   UNK     0    8699.8038699.912   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8705.1418702.993   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8706.4738702.223   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8707.8108702.993   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8709.1438702.223   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8707.8108704.534   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8703.8088702.222   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8702.4748702.992   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8701.1408702.222   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8701.1408700.682   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8702.4748699.912   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8703.8088700.682   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8702.4748698.369   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8703.8108697.598   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    7    3                                                       
CONECT    3    4    2                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    8   12    2                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    1                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dihydroconiferylic acid	ChEBI
3-(4-Hydroxy-3-methoxyphenyl)propionate	Generator
Dihydroconiferylate	Generator
Dihydroferulate	Generator
Hydroferulate	HMDB
(4-Hydroxy-3-methoxyphenyl)propionic acid	HMDB
3-(3'-Methoxy-4'-hydroxyphenyl)propionic acid	HMDB
3-(3-Methoxy-4-hydroxyphenyl)propanoic acid	HMDB
3-(3-Methoxy-4-hydroxyphenyl)propionic acid	HMDB
3-(3’-methoxy-4’-hydroxyphenyl)propionic acid	HMDB
3-(4-Hydroxy-3-methoxyphenyl)propanoic acid	HMDB
3-Methoxy-4-hydroxyphenylpropionic acid	HMDB
3-Methoxyphloretic acid	HMDB
4-Hydroxy-3-methoxybenzenepropanoic acid	HMDB
DHFA	HMDB
Shorbic acid	HMDB
beta-(4-Hydroxy-3-methoxyphenyl)propionic acid	HMDB
beta-3-Methoxy-4-hydroxyphenylpropionic acid	HMDB
Β-(4-hydroxy-3-methoxyphenyl)propionic acid	HMDB
Β-3-methoxy-4-hydroxyphenylpropionic acid	HMDB
3-(4'-Hydroxy-3'-methoxyphenyl)propanoic acid	HMDB
4-Hydroxy-3-methoxyhydrocinnamic acid	PhytoBank
4-Hydroxy-3-methoxybenzenepropionic acid	PhytoBank
(4-Hydroxy-3-methoxyphenyl)propanoic acid	PhytoBank
3-(3'-Methoxy-4'-hydroxyphenyl)propanoic acid	PhytoBank
3-(3’-Methoxy-4’-hydroxyphenyl)propanoic acid	PhytoBank
3-Methoxy-4-hydroxyphenylpropanoic acid	PhytoBank
alpha,beta-Dihydroferulic acid	PhytoBank
α,β-Dihydroferulic acid	PhytoBank
beta-(4-Hydroxy-3-methoxyphenyl)propanoic acid	PhytoBank
β-(4-Hydroxy-3-methoxyphenyl)propanoic acid	PhytoBank
beta-3-Methoxy-4-hydroxyphenylpropanoic acid	PhytoBank
β-3-Methoxy-4-hydroxyphenylpropanoic acid	PhytoBank
3-(4-Hydroxy-3-methoxyphenyl) propanoic acid	HMDB

Chemical Formula

C₁₀H₁₂O₄

Average Molecular Weight

196.1999

Monoisotopic Molecular Weight

196.073558872

IUPAC Name

3-(4-hydroxy-3-methoxyphenyl)propanoic acid

Traditional Name

homovanillinic acid

CAS Registry Number

1135-23-5

SMILES

COC1=CC(CCC(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)

InChI Key

BOLQJTPHPSDZHR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:86612 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 25646321)

Excreta

Biofluid or Excreta

Feces (PMID: 27015276)
Urine (PMID: 28157703)

Source

Exogenous

Exogenous (HMDB: HMDB0062121)

Food

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0062121)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0062121)

Tea

Tea products (HMDB: HMDB0062121)

Fat and oil

Olive oil (HMDB: HMDB0062121)

Fruit

Fruits (HMDB: HMDB0062121)

Vegetable

Vegetables (HMDB: HMDB0062121)

Legumes (HMDB: HMDB0062121)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0062121)

Nut

Nuts (HMDB: HMDB0062121)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0062121)

Endogenous

Plant

Plant (HMDB: HMDB0062121)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.3 g/L	ALOGPS
logP	1.03	ALOGPS
logP	1.59	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.95	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	4	ChemAxon
Refractivity	50.41 m³·mol⁻¹	ChemAxon
Polarizability	19.8 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	145.579	31661259
DarkChem	[M-H]-	144.076	31661259
DeepCCS	[M+H]+	144.021	30932474
DeepCCS	[M-H]-	141.663	30932474
DeepCCS	[M-2H]-	177.295	30932474
DeepCCS	[M+Na]+	152.552	30932474
AllCCS	[M+H]+	143.2	32859911
AllCCS	[M+H-H2O]+	139.0	32859911
AllCCS	[M+NH4]+	147.0	32859911
AllCCS	[M+Na]+	148.1	32859911
AllCCS	[M-H]-	142.4	32859911
AllCCS	[M+Na-2H]-	143.1	32859911
AllCCS	[M+HCOO]-	143.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydroferulic acid	COC1=CC(CCC(O)=O)=CC=C1O	3217.8	Standard polar	33892256
Dihydroferulic acid	COC1=CC(CCC(O)=O)=CC=C1O	1739.6	Standard non polar	33892256
Dihydroferulic acid	COC1=CC(CCC(O)=O)=CC=C1O	1748.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydroferulic acid,1TMS,isomer #1	COC1=CC(CCC(=O)O[Si](C)(C)C)=CC=C1O	1831.3	Semi standard non polar	33892256
Dihydroferulic acid,1TMS,isomer #2	COC1=CC(CCC(=O)O)=CC=C1O[Si](C)(C)C	1914.8	Semi standard non polar	33892256
Dihydroferulic acid,2TMS,isomer #1	COC1=CC(CCC(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1901.3	Semi standard non polar	33892256
Dihydroferulic acid,1TBDMS,isomer #1	COC1=CC(CCC(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2079.5	Semi standard non polar	33892256
Dihydroferulic acid,1TBDMS,isomer #2	COC1=CC(CCC(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2153.3	Semi standard non polar	33892256
Dihydroferulic acid,2TBDMS,isomer #1	COC1=CC(CCC(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2372.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroferulic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-0900000000-326c8295f745d6de85d0	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroferulic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-9053000000-50b6ef8efef449290129	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroferulic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroferulic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferulic acid 10V, Positive-QTOF	splash10-002b-0900000000-0e26134b0d0191f7ee92	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferulic acid 20V, Positive-QTOF	splash10-0ug1-0900000000-7168875369e00ead2dcd	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferulic acid 40V, Positive-QTOF	splash10-0kbr-5900000000-7d74ece7efd4fcc57d7a	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferulic acid 10V, Negative-QTOF	splash10-0002-0900000000-eb9b945ab0bf9d6f5dc3	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferulic acid 20V, Negative-QTOF	splash10-0002-1900000000-aa8130dbec23e196888a	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferulic acid 40V, Negative-QTOF	splash10-0a4l-7900000000-b403cda9802707e7ecbf	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferulic acid 10V, Positive-QTOF	splash10-002r-0900000000-b4f6ef22cb5f85d71bea	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferulic acid 20V, Positive-QTOF	splash10-000i-0900000000-0f31db1df2ab8b8671c3	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferulic acid 40V, Positive-QTOF	splash10-0kxr-9600000000-3d47fb450748aac59428	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferulic acid 10V, Negative-QTOF	splash10-0a4j-9500000000-1a3e759636e4322e4e58	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferulic acid 20V, Negative-QTOF	splash10-000i-4900000000-f63426aee31341317b0b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroferulic acid 40V, Negative-QTOF	splash10-000f-2900000000-a9a9315636f849a6d02a	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000600 +/- 0.000200 uM	Adult (>18 years old)	Both	Normal	25646321	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029987

KNApSAcK ID

C00040946

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14340

PDB ID

Not Available

ChEBI ID

86612

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Rechner AR, Spencer JP, Kuhnle G, Hahn U, Rice-Evans CA: Novel biomarkers of the metabolism of caffeic acid derivatives in vivo. Free Radic Biol Med. 2001 Jun 1;30(11):1213-22. [PubMed:11368919 ]
Redeuil K, Smarrito-Menozzi C, Guy P, Rezzi S, Dionisi F, Williamson G, Nagy K, Renouf M: Identification of novel circulating coffee metabolites in human plasma by liquid chromatography-mass spectrometry. J Chromatogr A. 2011 Jul 22;1218(29):4678-88. doi: 10.1016/j.chroma.2011.05.050. Epub 2011 May 26. [PubMed:21676405 ]
Ludwig IA, Paz de Pena M, Concepcion C, Alan C: Catabolism of coffee chlorogenic acids by human colonic microbiota. Biofactors. 2013 Nov-Dec;39(6):623-32. doi: 10.1002/biof.1124. Epub 2013 Aug 1. [PubMed:23904092 ]
Lang R, Dieminger N, Beusch A, Lee YM, Dunkel A, Suess B, Skurk T, Wahl A, Hauner H, Hofmann T: Bioappearance and pharmacokinetics of bioactives upon coffee consumption. Anal Bioanal Chem. 2013 Oct;405(26):8487-503. doi: 10.1007/s00216-013-7288-0. Epub 2013 Aug 28. [PubMed:23982107 ]
Stalmach A, Williamson G, Crozier A: Impact of dose on the bioavailability of coffee chlorogenic acids in humans. Food Funct. 2014 Aug;5(8):1727-37. doi: 10.1039/c4fo00316k. [PubMed:24947504 ]
Wang P, Chen H, Zhu Y, McBride J, Fu J, Sang S: Oat avenanthramide-C (2c) is biotransformed by mice and the human microbiota into bioactive metabolites. J Nutr. 2015 Feb;145(2):239-45. doi: 10.3945/jn.114.206508. Epub 2014 Dec 17. [PubMed:25644343 ]
Mills CE, Tzounis X, Oruna-Concha MJ, Mottram DS, Gibson GR, Spencer JP: In vitro colonic metabolism of coffee and chlorogenic acid results in selective changes in human faecal microbiota growth. Br J Nutr. 2015 Apr 28;113(8):1220-7. doi: 10.1017/S0007114514003948. Epub 2015 Mar 26. [PubMed:25809126 ]
Tan S, Calani L, Bresciani L, Dall'asta M, Faccini A, Augustin MA, Gras SL, Del Rio D: The degradation of curcuminoids in a human faecal fermentation model. Int J Food Sci Nutr. 2015;66(7):790-6. doi: 10.3109/09637486.2015.1095865. [PubMed:26471074 ]
Sanchez-Bridge B, Renouf M, Sauser J, Beaumont M, Actis-Goretta L: The roasting process does not influence the extent of conjugation of coffee chlorogenic and phenolic acids. Biofactors. 2016 May;42(3):259-67. doi: 10.1002/biof.1268. Epub 2016 Feb 22. [PubMed:26899568 ]
Vitaglione P, Mennella I, Ferracane R, Rivellese AA, Giacco R, Ercolini D, Gibbons SM, La Storia A, Gilbert JA, Jonnalagadda S, Thielecke F, Gallo MA, Scalfi L, Fogliano V: Whole-grain wheat consumption reduces inflammation in a randomized controlled trial on overweight and obese subjects with unhealthy dietary and lifestyle behaviors: role of polyphenols bound to cereal dietary fiber. Am J Clin Nutr. 2015 Feb;101(2):251-61. doi: 10.3945/ajcn.114.088120. Epub 2014 Dec 3. [PubMed:25646321 ]
Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Dihydroferulic acid → 6-[4-(2-carboxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Dihydroferulic acid → 3,4,5-trihydroxy-6-{[3-(4-hydroxy-3-methoxyphenyl)propanoyl]oxy}oxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

Dihydroferulic acid → Dihydroferulic acid 4-O-sulfate	details

Showing metabocard for Dihydroferulic acid (HMDB0062121)

MOL for HMDB0062121 (Dihydroferulic acid)

3D MOL for HMDB0062121 (Dihydroferulic acid)

3D SDF for HMDB0062121 (Dihydroferulic acid)

3D-SDF for HMDB0062121 (Dihydroferulic acid)

PDB for HMDB0062121 (Dihydroferulic acid)

3D PDB for HMDB0062121 (Dihydroferulic acid)

SMILES for HMDB0062121 (Dihydroferulic acid)

INCHI for HMDB0062121 (Dihydroferulic acid)

Structure for HMDB0062121 (Dihydroferulic acid)

3D Structure for HMDB0062121 (Dihydroferulic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions