Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-04-03 14:10:30 UTC

Update Date

2023-02-21 17:18:00 UTC

HMDB ID

HMDB0013677

Secondary Accession Numbers

HMDB13677

Metabolite Identification

Common Name

3,5-Dihydroxybenzoic acid

Description

3,5-Dihydroxybenzoic acid, also known as alpha-resorcylic acid or a-resorcylate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,5-Dihydroxybenzoic acid is found, on average, in the highest concentration within beer. 3,5-Dihydroxybenzoic acid has also been detected, but not quantified in, several different foods, such as grape wine, nuts, peanuts (Arachis hypogaea), and pulses. This could make 3,5-dihydroxybenzoic acid a potential biomarker for the consumption of these foods. 3,5-Dihydroxybenzoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 3,5-Dihydroxybenzoic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha-Resorcylic acid	ChEBI
a-Resorcylate	Generator
a-Resorcylic acid	Generator
alpha-Resorcylate	Generator
Α-resorcylate	Generator
Α-resorcylic acid	Generator
3,5-Dihydroxybenzoate	Generator
3,5-Dihydroxy-benzoic acid	HMDB
3,5-Dihydroxybenzoic acid (acd/name 4.0)	HMDB
5-Carboxyresorcinol	HMDB
Benzoate	HMDB
Benzoic acid	HMDB
alpha-Resorcylic acid, copper (2+) salt	MeSH, HMDB
alpha-Resorcylic acid, sodium salt	MeSH, HMDB
3,5-DHBA	HMDB
3,5-Dihydroxybenzoic acid	HMDB

Chemical Formula

C₇H₆O₄

Average Molecular Weight

154.121

Monoisotopic Molecular Weight

154.026608673

IUPAC Name

3,5-dihydroxybenzoic acid

Traditional Name

3,5-dihydroxybenzoic acid

CAS Registry Number

99-10-5

SMILES

OC(=O)C1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C7H6O4/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,8-9H,(H,10,11)

InChI Key

UYEMGAFJOZZIFP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Hydroxybenzoic acid
Benzoic acid
Resorcinol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

resorcinols (CHEBI:39912 )
dihydroxybenzoic acid (CHEBI:39912 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0013677)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0013677)
Urine (HMDB: HMDB0013677)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013677)

Source

Endogenous

Endogenous (HMDB: HMDB0013677)

Plant

Plant (HMDB: HMDB0013677)
Fabaceae (HMDB: HMDB0013677)

Exogenous

Food

Food (HMDB: HMDB0013677)
Legumes (HMDB: HMDB0013677)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Alcoholic beverage

Red wine (HMDB: HMDB0013677)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0013677)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0013677)

Tea

Tea products (HMDB: HMDB0013677)

Fat and oil

Olive oil (HMDB: HMDB0013677)

Fruit

Fruits (HMDB: HMDB0013677)

Vegetable

Vegetables (HMDB: HMDB0013677)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0013677)

Nut

Nuts (HMDB: HMDB0013677)
Peanut (FooDB: FOOD00016)

Pulse

Pulses (FooDB: FOOD00867)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	237 °C	Not Available
Boiling Point	411.00 to 412.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	50980 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.86	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12 g/L	ALOGPS
logP	1.29	ALOGPS
logP	1.02	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.28 m³·mol⁻¹	ChemAxon
Polarizability	13.88 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	133.632	31661259
DarkChem	[M-H]-	129.634	31661259
DeepCCS	[M+H]+	131.14	30932474
DeepCCS	[M-H]-	127.558	30932474
DeepCCS	[M-2H]-	165.197	30932474
DeepCCS	[M+Na]+	140.736	30932474
AllCCS	[M+H]+	132.2	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	136.5	32859911
AllCCS	[M+Na]+	137.7	32859911
AllCCS	[M-H]-	125.4	32859911
AllCCS	[M+Na-2H]-	126.7	32859911
AllCCS	[M+HCOO]-	128.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dihydroxybenzoic acid	OC(=O)C1=CC(O)=CC(O)=C1	3326.3	Standard polar	33892256
3,5-Dihydroxybenzoic acid	OC(=O)C1=CC(O)=CC(O)=C1	1611.1	Standard non polar	33892256
3,5-Dihydroxybenzoic acid	OC(=O)C1=CC(O)=CC(O)=C1	1705.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dihydroxybenzoic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O)=CC(O)=C1	1849.8	Semi standard non polar	33892256
3,5-Dihydroxybenzoic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC(C(=O)O)=C1	1788.1	Semi standard non polar	33892256
3,5-Dihydroxybenzoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O)=CC(O[Si](C)(C)C)=C1	1824.9	Semi standard non polar	33892256
3,5-Dihydroxybenzoic acid,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=CC(C(=O)O)=C1	1811.1	Semi standard non polar	33892256
3,5-Dihydroxybenzoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1	1812.3	Semi standard non polar	33892256
3,5-Dihydroxybenzoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC(O)=C1	2091.3	Semi standard non polar	33892256
3,5-Dihydroxybenzoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(C(=O)O)=C1	2051.8	Semi standard non polar	33892256
3,5-Dihydroxybenzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1	2294.5	Semi standard non polar	33892256
3,5-Dihydroxybenzoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C(=O)O)=C1	2302.0	Semi standard non polar	33892256
3,5-Dihydroxybenzoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1	2487.1	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 - 3,5-Dihydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-2900000000-46dcc0b7ed6c27ee5f7c	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dihydroxybenzoic acid GC-MS (3 TMS) - 70eV, Positive	splash10-05ai-4092000000-a4387f9715089c352d97	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dihydroxybenzoic 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 15V, Negative-QTOF	Not Available	2019-09-10	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 40V, Negative-QTOF	splash10-0019-9000000000-8b567108e3513c709ebd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 20V, Negative-QTOF	splash10-014i-9300000000-7f42a86a9537534fc938	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 10V, Negative-QTOF	splash10-0a4i-1900000000-44e9110e4a5fb09d17c2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 10V, Positive-QTOF	splash10-0a4i-0900000000-004ea53dae9593c251b3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 20V, Positive-QTOF	splash10-0a4i-0900000000-8314761384814f791220	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 40V, Positive-QTOF	splash10-03dl-9700000000-9ee7d6c075af3dc0245c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 10V, Negative-QTOF	splash10-0udi-0900000000-0fd6d253983c87b951d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 20V, Negative-QTOF	splash10-0pb9-0900000000-fceb71e190d0e9b6a22a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 40V, Negative-QTOF	splash10-0a4i-7900000000-3f3552574ef874889467	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 10V, Positive-QTOF	splash10-0bti-0900000000-74eac3492e2dc880b739	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 20V, Positive-QTOF	splash10-052r-1900000000-e54b4355f1c22f9d7ba6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 40V, Positive-QTOF	splash10-014r-9100000000-e2fcd97e4e6a1d18054a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 10V, Negative-QTOF	splash10-0pb9-0900000000-8723f5ec68dd69c226c8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 20V, Negative-QTOF	splash10-0a4i-0900000000-83aa7ada53ca7119e12b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 40V, Negative-QTOF	splash10-00kf-9000000000-d56c533cac680e72de25	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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
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	0.0940 +/- 0.0820 uM	Adult (>18 years old)	Female	Normal	19874633	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected and Quantified	0.091 +/- 0.029 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.035 +/- 0.019 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.069 +/- 0.028 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.297 +/- 0.185 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.065 +/- 0.024 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.101 +/- 0.045 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.066 +/- 0.03 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.4 +/- 0.268 uM	Adult (>18 years old)	Male	Normal	19812218	details
Feces	Detected and Quantified	1.168 +/- 0.843 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	1.168 +/- 1.363 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	1.363 +/- 1.0382 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	2.271 +/- 1.363 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 436	12771321	details
Urine	Detected and Quantified	1.613 +/- 1.0400 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	18768490	details
Urine	Detected and Quantified	2.187 +/- 1.440 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	18768490	details
Urine	Detected and Quantified	0.33 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	22437553	details
Urine	Detected and Quantified	0.42 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	22437553	details
Urine	Detected and Quantified	1.787 +/- 1.0400 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	18768490	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.269 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.0150-1.990 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Detected and Quantified	0.218 +/- 0.124 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

CPD0-1274

BiGG ID

Not Available

Wikipedia Link

3,5-Dihydroxybenzoic_acid

METLIN ID

Not Available

PubChem Compound

7424

PDB ID

Not Available

ChEBI ID

39912

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1184651

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Elemans JA, Boerakker MJ, Holder SJ, Rowan AE, Cho WD, Percec V, Nolte RJ: Plastic- and liquid-crystalline architectures from dendritic receptor molecules. Proc Natl Acad Sci U S A. 2002 Apr 16;99(8):5093-8. [PubMed:11959959 ]
Ross AB, Aman P, Kamal-Eldin A: Identification of cereal alkylresorcinol metabolites in human urine-potential biomarkers of wholegrain wheat and rye intake. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Sep 25;809(1):125-30. doi: 10.1016/j.jchromb.2004.06.015. [PubMed:15282102 ]
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

3,5-Dihydroxybenzoic acid → 6-(3-carboxy-5-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
3,5-Dihydroxybenzoic acid → 6-(3,5-dihydroxybenzoyloxy)-3,4,5-trihydroxyoxane-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

3,5-Dihydroxybenzoic acid → 2-{[(3,5-dihydroxyphenyl)(hydroxy)methylidene]amino}acetic acid	details

Showing metabocard for 3,5-Dihydroxybenzoic acid (HMDB0013677)

MOL for HMDB0013677 (3,5-Dihydroxybenzoic acid)

3D MOL for HMDB0013677 (3,5-Dihydroxybenzoic acid)

3D SDF for HMDB0013677 (3,5-Dihydroxybenzoic acid)

3D-SDF for HMDB0013677 (3,5-Dihydroxybenzoic acid)

PDB for HMDB0013677 (3,5-Dihydroxybenzoic acid)

3D PDB for HMDB0013677 (3,5-Dihydroxybenzoic acid)

SMILES for HMDB0013677 (3,5-Dihydroxybenzoic acid)

INCHI for HMDB0013677 (3,5-Dihydroxybenzoic acid)

Structure for HMDB0013677 (3,5-Dihydroxybenzoic acid)

3D Structure for HMDB0013677 (3,5-Dihydroxybenzoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions