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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:35 UTC

Update Date

2023-02-21 17:16:08 UTC

HMDB ID

HMDB0002085

Secondary Accession Numbers

HMDB02085

Metabolite Identification

Common Name

Syringic acid

Description

Syringic acid, also known as syringate or cedar acid, belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. Outside of the human body, Syringic acid is found, on average, in the highest concentration within a few different foods, such as common walnuts, swiss chards, and olives and in a lower concentration in apples, tarragons, and peanuts. Syringic acid has also been detected, but not quantified in several different foods, such as sweet marjorams, silver lindens, bulgurs, annual wild rices, and barley. This could make syringic acid a potential biomarker for the consumption of these foods. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. Research suggests that phenolics from wine may play a positive role against oxidation of low-density lipoprotein (LDL), which is a key step in the development of atherosclerosis. Syringic acid is a phenol present in some distilled alcohol beverages. It is also a product of microbial (gut) metabolism of anthocyanins and other polyphenols that have been consumed (in fruits and alcoholic beverages - PMID:18767860 ). Syringic acid is also a microbial metabolite that can be found in Bifidobacterium (PMID:24958563 ).

Structure

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

Syringic acid
  Mrv1652305201900042D          

 14 14  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002085

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(OC)=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O5/c1-13-6-3-5(9(11)12)4-7(14-2)8(6)10/h3-4,10H,1-2H3,(H,11,12)

> <INCHI_KEY>
JMSVCTWVEWCHDZ-UHFFFAOYSA-N

> <FORMULA>
C9H10O5

> <MOLECULAR_WEIGHT>
198.174

> <EXACT_MASS>
198.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.770948525158104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3,5-dimethoxybenzoic acid

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.0119208709999998

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.550188846644089

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.931934806367758

> <JCHEM_PKA_STRONGEST_BASIC>
-4.61219102745602

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
48.221500000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
syringic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Syringic acid                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Cedar acid	ChEBI
Gallic acid 3,5-dimethyl ether	ChEBI
Syringate	Kegg
4-Hydroxy-3,5-dimethoxybenzoate	Kegg
Gallate 3,5-dimethyl ether	Generator
4-Hydroxy-3,5-dimethoxybenzoic acid	Generator
Syringic acid cu (+2) salt (1:1)	MeSH
3,5-Dimethoxy-4-hydroxybenzoate	HMDB
3,5-Dimethoxy-4-hydroxybenzoic acid	HMDB
3,5-Dimethoxybenzoyl hydrazine	HMDB
3,5-Dimethyl-4-hydroxybenzoate	HMDB
3,5-Dimethyl-4-hydroxybenzoic acid	HMDB
4-Hydroxy-3,5-dimethylbenzoate	HMDB
4-Hydroxy-3,5-dimethylbenzoic acid	HMDB
Syringlicacid	HMDB
Syringic acid	HMDB
3,5-dimethoxygallic acid	HMDB
3,5-O-dimethylgallic acid	HMDB

Chemical Formula

C₉H₁₀O₅

Average Molecular Weight

198.174

Monoisotopic Molecular Weight

198.052823422

IUPAC Name

4-hydroxy-3,5-dimethoxybenzoic acid

Traditional Name

syringic acid

CAS Registry Number

530-57-4

SMILES

COC1=CC(=CC(OC)=C1O)C(O)=O

InChI Identifier

InChI=1S/C9H10O5/c1-13-6-3-5(9(11)12)4-7(14-2)8(6)10/h3-4,10H,1-2H3,(H,11,12)

InChI Key

JMSVCTWVEWCHDZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acid and derivatives

Alternative Parents

Substituents

Gallic acid or derivatives
M-methoxybenzoic acid or derivatives
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
Alkyl aryl ether
Phenol
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:68329 )
dimethoxybenzene (CHEBI:68329 )
benzoic acids (CHEBI:68329 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0002085)
Saliva (HMDB: HMDB0002085)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0002085)
Urine (HMDB: HMDB0002085)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002085)

Source

Exogenous

Food

Food (HMDB: HMDB0002085)
Legumes (HMDB: HMDB0002085)

Beverage

Fermented beverage

Distilled beverage

Spirit (FooDB: FOOD00276)
Liquor (FooDB: FOOD00616)
Rum (FooDB: FOOD00629)
Whisky (FooDB: FOOD00623)

Alcoholic beverage

Red wine (HMDB: HMDB0002085)

Fortified wines

Sherry (FooDB: FOOD00632)

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Berry

Tropical fruit

Coconut (FooDB: FOOD00336)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)

Fruits (HMDB: HMDB0002085)

Vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Olive (FooDB: FOOD00121)
Garden tomato (FooDB: FOOD00171)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)

Root vegetable

Cabbage

Broccoli (FooDB: FOOD00034)
Cauliflower (FooDB: FOOD00031)

Leaf vegetable

Swiss chard (FooDB: FOOD00237)
Romaine lettuce (FooDB: FOOD00888)

Vegetables (HMDB: HMDB0002085)

Tuber

Arrowroot (FooDB: FOOD00290)

Cereal and cereal product

Cereal

Cereal product

Breakfast cereal (FooDB: FOOD00270)
Whole grain cereal products (HMDB: HMDB0002085)
Flour (FooDB: FOOD00799)
Bulgur (FooDB: FOOD00741)

Leavened bread

Rye bread (FooDB: FOOD00809)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Pea

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Cocoa and cocoa product

Cocoa product

Cocoa powder (FooDB: FOOD00685)

Cocoa and cocoa products (HMDB: HMDB0002085)

Cocoa

Cocoa bean (FooDB: FOOD00182)

Coffee and coffee product

Coffee

Coffee product

Coffee products (HMDB: HMDB0002085)

Sunflower (FooDB: FOOD00086)
Evening primrose (FooDB: FOOD00120)

Other seed

Quinoa (FooDB: FOOD00441)

Gourd

Tea

Tea products (HMDB: HMDB0002085)

Fat and oil

Olive oil (HMDB: HMDB0002085)

Nut

Baking good

Seasoning

Vinegar (FooDB: FOOD00628)

Endogenous

Plant

Microbe

Microbe (HMDB: HMDB0002085)
Bifidobacterium (HMDB: HMDB0002085)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0002085)
Antioxidant (HMDB: HMDB0002085)

Biological role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	206 - 209 °C	Not Available
Boiling Point	440.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	5783 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.04	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.71 g/L	ALOGPS
logP	1.55	ALOGPS
logP	1.01	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.93	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.22 m³·mol⁻¹	ChemAxon
Polarizability	18.77 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]+	145.704	31661259
DarkChem	[M-H]-	143.53	31661259
DeepCCS	[M+H]+	140.285	30932474
DeepCCS	[M-H]-	136.458	30932474
DeepCCS	[M-2H]-	173.901	30932474
DeepCCS	[M+Na]+	149.439	30932474
AllCCS	[M+H]+	142.8	32859911
AllCCS	[M+H-H2O]+	138.7	32859911
AllCCS	[M+NH4]+	146.6	32859911
AllCCS	[M+Na]+	147.8	32859911
AllCCS	[M-H]-	139.4	32859911
AllCCS	[M+Na-2H]-	140.1	32859911
AllCCS	[M+HCOO]-	140.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Syringic acid	COC1=CC(=CC(OC)=C1O)C(O)=O	2926.0	Standard polar	33892256
Syringic acid	COC1=CC(=CC(OC)=C1O)C(O)=O	1714.7	Standard non polar	33892256
Syringic acid	COC1=CC(=CC(OC)=C1O)C(O)=O	1837.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Syringic acid,1TMS,isomer #1	COC1=CC(C(=O)O)=CC(OC)=C1O[Si](C)(C)C	1837.5	Semi standard non polar	33892256
Syringic acid,1TMS,isomer #2	COC1=CC(C(=O)O[Si](C)(C)C)=CC(OC)=C1O	1865.4	Semi standard non polar	33892256
Syringic acid,2TMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	1901.1	Semi standard non polar	33892256
Syringic acid,1TBDMS,isomer #1	COC1=CC(C(=O)O)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	2126.6	Semi standard non polar	33892256
Syringic acid,1TBDMS,isomer #2	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	2124.0	Semi standard non polar	33892256
Syringic acid,2TBDMS,isomer #1	COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	2389.5	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 - Syringic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f8a-0900000000-7b568e18ffde6ab04131	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Syringic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-8095000000-575a6ec78ed017731cc6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Syringic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-5900000000-0b6163fb3f78b99ad5dd	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-052f-0900000000-14ec0ce09465c51ccc37	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-004l-9800000000-9765822b3b1e2ec9d9de	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-004j-9100000000-8d01bd5b04dae916e4aa	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0002-0900000000-0a0256c7bc33c2d88a4e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0fka-0900000000-254d42fb132329839152	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-00di-1900000000-304c5119148e7f55f4d6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-00b9-9500000000-49a00cfe65ce9eabeb4c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-004r-9000000000-80475497b3098dd00777	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid LC-ESI-QQ , negative-QTOF	splash10-0002-0900000000-0a0256c7bc33c2d88a4e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid LC-ESI-QQ , negative-QTOF	splash10-0fka-0900000000-254d42fb132329839152	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid LC-ESI-QQ , negative-QTOF	splash10-00di-1900000000-01d0ea76c3ba0db41782	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid LC-ESI-QQ , negative-QTOF	splash10-00b9-9500000000-49a00cfe65ce9eabeb4c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid LC-ESI-QQ , negative-QTOF	splash10-004r-9000000000-80475497b3098dd00777	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid Linear Ion Trap , negative-QTOF	splash10-0f89-0900000000-87ada1ca48a49d9677dd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid Linear Ion Trap , positive-QTOF	splash10-001i-0900000000-019cee52e59a254e3fcf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid 20V, Negative-QTOF	splash10-00di-5900000000-a4ed976f907f00dd365e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid 10V, Negative-QTOF	splash10-00di-1900000000-b7c04f3e2902703c2579	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid 10V, Negative-QTOF	splash10-0uk9-0900000000-49feaba426346d2e61f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Syringic acid 35V, Positive-QTOF	splash10-002f-3900000000-023a912267ff680b287c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Syringic acid 10V, Positive-QTOF	splash10-0002-0900000000-6ce63e339a947f904864	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Syringic acid 20V, Positive-QTOF	splash10-001j-0900000000-a397243a2d8f8f9e501d	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Syringic acid 40V, Positive-QTOF	splash10-001r-2900000000-d3241b91846d43efb768	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Syringic acid 10V, Negative-QTOF	splash10-0002-0900000000-e699dd409e203e12842f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Syringic acid 20V, Negative-QTOF	splash10-0uds-0900000000-b5bde1ce65999b3cf7de	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Syringic acid 40V, Negative-QTOF	splash10-0fa9-2900000000-87c04717df825474388d	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.0-7.1 uM	Adult (>18 years old)	Male	Normal	16019270	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected and Quantified	2.119 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	3.885 +/- 1.867 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	9.285 +/- 5.601 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	2.155 (0.121-6.0704) nmol/g wet feces	Adult (>18 years old)	Both	Normal	28029051	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected and Quantified	1.57 +/- 0.123 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.59 +/- 0.118 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.62 +/- 0.105 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.71 +/- 0.0913 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 420	12771321	details
Urine	Detected and Quantified	0.9 +/- 0.2 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	16939358	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	1.5 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	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	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hypertension (mild)	20013882	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Syringic_acid

METLIN ID

2256

PubChem Compound

10742

PDB ID

Not Available

ChEBI ID

68329

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1285301

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Kalkan Yildirim H, Delen Akcay Y, Guvenc U, Yildirim Sozmen E: Protection capacity against low-density lipoprotein oxidation and antioxidant potential of some organic and non-organic wines. Int J Food Sci Nutr. 2004 Aug;55(5):351-62. [PubMed:15545043 ]
Forester SC, Waterhouse AL: Identification of Cabernet Sauvignon anthocyanin gut microflora metabolites. J Agric Food Chem. 2008 Oct 8;56(19):9299-304. doi: 10.1021/jf801309n. Epub 2008 Sep 4. [PubMed:18767860 ]
Boto-Ordonez M, Urpi-Sarda M, Queipo-Ortuno MI, Tulipani S, Tinahones FJ, Andres-Lacueva C: High levels of Bifidobacteria are associated with increased levels of anthocyanin microbial metabolites: a randomized clinical trial. Food Funct. 2014 Aug;5(8):1932-8. doi: 10.1039/c4fo00029c. [PubMed:24958563 ]

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

Syringic acid → 6-(4-carboxy-2,6-dimethoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Syringic acid → 3,4,5-trihydroxy-6-(4-hydroxy-3,5-dimethoxybenzoyloxy)oxane-2-carboxylic acid	details

Enzyme Details

2. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Reactions

Syringic acid → 2-{[hydroxy(4-hydroxy-3,5-dimethoxyphenyl)methylidene]amino}acetic acid	details

Enzyme Details

3. 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

Syringic acid → 3,5-dimethoxy-4-(sulfooxy)benzoic acid	details

Showing metabocard for Syringic acid (HMDB0002085)

MOL for HMDB0002085 (Syringic acid)

3D MOL for HMDB0002085 (Syringic acid)

3D SDF for HMDB0002085 (Syringic acid)

3D-SDF for HMDB0002085 (Syringic acid)

PDB for HMDB0002085 (Syringic acid)

3D PDB for HMDB0002085 (Syringic acid)

SMILES for HMDB0002085 (Syringic acid)

INCHI for HMDB0002085 (Syringic acid)

Structure for HMDB0002085 (Syringic acid)

3D Structure for HMDB0002085 (Syringic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions