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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-04-03 14:10:30 UTC
Update Date2021-10-13 05:41:06 UTC
HMDB IDHMDB0013677
Secondary Accession Numbers
  • HMDB13677
Metabolite Identification
Common Name3,5-Dihydroxybenzoic acid
Description3,5-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
Data?1582753142
Synonyms
ValueSource
alpha-Resorcylic acidChEBI
a-ResorcylateGenerator
a-Resorcylic acidGenerator
alpha-ResorcylateGenerator
Α-resorcylateGenerator
Α-resorcylic acidGenerator
3,5-DihydroxybenzoateGenerator
3,5-Dihydroxy-benzoic acidHMDB
3,5-Dihydroxybenzoic acid (acd/name 4.0)HMDB
5-CarboxyresorcinolHMDB
BenzoateHMDB
Benzoic acidHMDB
alpha-Resorcylic acid, copper (2+) saltMeSH, HMDB
alpha-Resorcylic acid, sodium saltMeSH, HMDB
3,5-DHBAHMDB
3,5-Dihydroxybenzoic acidHMDB
Chemical FormulaC7H6O4
Average Molecular Weight154.121
Monoisotopic Molecular Weight154.026608673
IUPAC Name3,5-dihydroxybenzoic acid
Traditional Name3,5-dihydroxybenzoic acid
CAS Registry Number99-10-5
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 KeyUYEMGAFJOZZIFP-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point237 °CNot Available
Boiling Point411.00 to 412.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility50980 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.86Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility12 g/LALOGPS
logP1.29ALOGPS
logP1.02ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m³·mol⁻¹ChemAxon
Polarizability13.88 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.63231661259
DarkChem[M-H]-129.63431661259
DeepCCS[M+H]+131.1430932474
DeepCCS[M-H]-127.55830932474
DeepCCS[M-2H]-165.19730932474
DeepCCS[M+Na]+140.73630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,5-Dihydroxybenzoic acidOC(=O)C1=CC(O)=CC(O)=C13326.3Standard polar33892256
3,5-Dihydroxybenzoic acidOC(=O)C1=CC(O)=CC(O)=C11611.1Standard non polar33892256
3,5-Dihydroxybenzoic acidOC(=O)C1=CC(O)=CC(O)=C11705.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,5-Dihydroxybenzoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O)=CC(O)=C11849.8Semi standard non polar33892256
3,5-Dihydroxybenzoic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC(C(=O)O)=C11788.1Semi standard non polar33892256
3,5-Dihydroxybenzoic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O)=CC(O[Si](C)(C)C)=C11824.9Semi standard non polar33892256
3,5-Dihydroxybenzoic acid,2TMS,isomer #2C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=CC(C(=O)O)=C11811.1Semi standard non polar33892256
3,5-Dihydroxybenzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C11812.3Semi standard non polar33892256
3,5-Dihydroxybenzoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC(O)=C12091.3Semi standard non polar33892256
3,5-Dihydroxybenzoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(C(=O)O)=C12051.8Semi standard non polar33892256
3,5-Dihydroxybenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C12294.5Semi standard non polar33892256
3,5-Dihydroxybenzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C(=O)O)=C12302.0Semi standard non polar33892256
3,5-Dihydroxybenzoic acid,3TBDMS,isomer #1CC(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)=C12487.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Dihydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-2900000000-46dcc0b7ed6c27ee5f7c2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Dihydroxybenzoic acid GC-MS (3 TMS) - 70eV, Positivesplash10-05ai-4092000000-a4387f9715089c352d972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,5-Dihydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 15V, Negative-QTOFNot Available2019-09-10HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 40V, Negative-QTOFsplash10-0019-9000000000-8b567108e3513c709ebd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 20V, Negative-QTOFsplash10-014i-9300000000-7f42a86a9537534fc9382021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 10V, Negative-QTOFsplash10-0a4i-1900000000-44e9110e4a5fb09d17c22021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 10V, Positive-QTOFsplash10-0a4i-0900000000-004ea53dae9593c251b32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 20V, Positive-QTOFsplash10-0a4i-0900000000-8314761384814f7912202016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 40V, Positive-QTOFsplash10-03dl-9700000000-9ee7d6c075af3dc0245c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 10V, Negative-QTOFsplash10-0udi-0900000000-0fd6d253983c87b951d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 20V, Negative-QTOFsplash10-0pb9-0900000000-fceb71e190d0e9b6a22a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 40V, Negative-QTOFsplash10-0a4i-7900000000-3f3552574ef8748894672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 10V, Positive-QTOFsplash10-0bti-0900000000-74eac3492e2dc880b7392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 20V, Positive-QTOFsplash10-052r-1900000000-e54b4355f1c22f9d7ba62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 40V, Positive-QTOFsplash10-014r-9100000000-e2fcd97e4e6a1d18054a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 10V, Negative-QTOFsplash10-0pb9-0900000000-8723f5ec68dd69c226c82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 20V, Negative-QTOFsplash10-0a4i-0900000000-83aa7ada53ca7119e12b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,5-Dihydroxybenzoic acid 40V, Negative-QTOFsplash10-00kf-9000000000-d56c533cac680e72de252021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0940 +/- 0.0820 uMAdult (>18 years old)FemaleNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
BloodDetected and Quantified0.091 +/- 0.029 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.035 +/- 0.019 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.069 +/- 0.028 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.297 +/- 0.185 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.065 +/- 0.024 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.101 +/- 0.045 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.066 +/- 0.03 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.4 +/- 0.268 uMAdult (>18 years old)Male
Normal
details
FecesDetected and Quantified1.168 +/- 0.843 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified1.168 +/- 1.363 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified1.363 +/- 1.0382 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified2.271 +/- 1.363 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 436 details
UrineDetected and Quantified1.613 +/- 1.0400 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified2.187 +/- 1.440 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified0.33 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.42 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified1.787 +/- 1.0400 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.269 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0150-1.990 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.218 +/- 0.124 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID436
FooDB IDFDB000848
KNApSAcK IDC00016318
Chemspider ID7146
KEGG Compound IDNot Available
BioCyc IDCPD0-1274
BiGG IDNot Available
Wikipedia Link3,5-Dihydroxybenzoic_acid
METLIN IDNot Available
PubChem Compound7424
PDB IDNot Available
ChEBI ID39912
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1184651
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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

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 aciddetails
3,5-Dihydroxybenzoic acid → 6-(3,5-dihydroxybenzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
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 aciddetails