MiMeDB: Showing metabocard for 3,5-Dihydroxybenzoic acid (MMDBc0000463)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:38:20 UTC

Update Date

2024-10-15 21:39:10 UTC

Metabolite ID

MMDBc0000463

Metabolite Identification

Common Name

3,5-Dihydroxybenzoic acid

Description

3,5-Dihydroxybenzoic acid (3,5-DHBA) is a primary metabolite of alkylresorcinols which has been hydrolyzed by liver enzymes during phase I metabolism after several cycles of beta-oxidation. 3,5-Dihydroxybenzoic acid is a potential urinary biomarker of whole grain intake (PMID: 15282102 ).

Structure

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

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

Molecular Formula

C₇H₆O₄

Average Mass

154.121

Monoisotopic Mass

154.026608673

IUPAC Name

3,5-dihydroxybenzoic acid

Traditional Name

3,5-dihydroxybenzoic acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-2900000000-46dcc0b7ed6c27ee5f7c	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-05ai-4092000000-a4387f9715089c352d97	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 15V, Negative	Not Available	2019-09-10	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0019-9000000000-8b567108e3513c709ebd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9300000000-7f42a86a9537534fc938	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1900000000-44e9110e4a5fb09d17c2	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-004ea53dae9593c251b3	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-8314761384814f791220	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9700000000-9ee7d6c075af3dc0245c	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-0fd6d253983c87b951d2	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-0900000000-fceb71e190d0e9b6a22a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-7900000000-3f3552574ef874889467	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bti-0900000000-74eac3492e2dc880b739	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-1900000000-e54b4355f1c22f9d7ba6	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014r-9100000000-e2fcd97e4e6a1d18054a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-0900000000-8723f5ec68dd69c226c8	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-83aa7ada53ca7119e12b	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-d56c533cac680e72de25	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

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
MMDBp0194143	Glycine N-acyltransferase	Enzyme	Q6IB77	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food			FooDB	Manually Annotated
Food			FooDB	Phenol Explorer
Food			FooDB	Julia Wannenmacher, Martina Gastl, and Thomas Becker. Phenolic Substances in Beer: Structural Diversity, Reactive Potential and Relevance for Brewing Process and Beer Quality. Comprehensive Reviews in Food Science and Food Safety, 2018, 17, 953-988. doi:10.1111/1541-4337.12352
Plant	Plant	Arachis hypogaea	FooDB	DUKE

Source Type	Activity	Data Source	Reference
General Exposome	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	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 Urine	Detected and Quantified	0.269				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Urine	Detected and Quantified	0.33				umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	22437553
Human Urine	Detected and Quantified	0.42				umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	22437553
Human Urine	Detected and Quantified			0.0150	1.990	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Blood	Detected and Quantified	0.035	0.019			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.065	0.024			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.066	0.03			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.069	0.028			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.091	0.029			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.0940	0.0820			uM	Adult (>18 years old)	Female	Normal	HMDB	19874633
Human Blood	Detected and Quantified	0.101	0.045			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected and Quantified	0.218	0.124			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.297	0.185			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Blood	Detected and Quantified	0.4	0.268			uM	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Feces	Detected and Quantified	1.168	0.843			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	1.168	1.363			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Feces	Detected and Quantified	1.363	1.0382			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
Human Urine	Detected and Quantified	1.613	1.0400			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	18768490
Human Urine	Detected and Quantified	1.787	1.0400			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	18768490
Human Urine	Detected and Quantified	2.187	1.440			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	18768490
Human Feces	Detected and Quantified	2.271	1.363			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	24010549
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

HMDB0013677

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

References

Synthesis Reference

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. doi: 10.1073/pnas.072018999. [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). Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510. University of Eastern Finland.

Showing metabocard for 3,5-Dihydroxybenzoic acid (MMDBc0000463)

MOL for #<Metabolite:0x00007fdb71b7c128>

3D MOL for #<Metabolite:0x00007fdb71b7c128>

3D SDF for #<Metabolite:0x00007fdb71b7c128>

3D-SDF for #<Metabolite:0x00007fdb71b7c128>

PDB for #<Metabolite:0x00007fdb71b7c128>

3D PDB for #<Metabolite:0x00007fdb71b7c128>

SMILES for #<Metabolite:0x00007fdb71b7c128>

INCHI for #<Metabolite:0x00007fdb71b7c128>

Structure for #<Metabolite:0x00007fdb71b7c128>

3D Structure for #<Metabolite:0x00007fdb71b7c128>