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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-08-01 02:20:38 UTC

Update Date

2023-02-21 17:31:18 UTC

HMDB ID

HMDB0094709

Secondary Accession Numbers

HMDB94709

Metabolite Identification

Common Name

3, 5-Dihydroxyphenylacetic acid

Description

3, 5-Dihydroxyphenylacetic acid belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. 3, 5-Dihydroxyphenylacetic 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-Dihydroxyphenylacetic acid.

Structure

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

HEADER    PROTEIN                                 01-AUG-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-AUG-17         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   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  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    5    6                                                       
CONECT    2    5    7                                                       
CONECT    3    5    8                                                       
CONECT    4    6    7                                                       
CONECT    5    1    2    3                                                  
CONECT    6    1    4    9                                                  
CONECT    7    2    4   10                                                  
CONECT    8    3   11   12                                                  
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(3,5-Dihydroxyphenyl)acetic acid	ChEBI
3,5-Dihydroxyphenylacetic acid	ChEBI
2-(3,5-Dihydroxyphenyl)acetate	Generator
3,5-Dihydroxyphenylacetate	Generator
3, 5-Dihydroxyphenylacetate	Generator

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.148

Monoisotopic Molecular Weight

168.042258738

IUPAC Name

2-(3,5-dihydroxyphenyl)acetic acid

Traditional Name

(3,5-dihydroxyphenyl)acetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C8H8O4/c9-6-1-5(3-8(11)12)2-7(10)4-6/h1-2,4,9-10H,3H2,(H,11,12)

InChI Key

IOVOJJDSFSXJQN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0094709)

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
logP	0.88	ALOGPS
logP	1	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.59	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	2	ChemAxon
Refractivity	41.33 m³·mol⁻¹	ChemAxon
Polarizability	15.75 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]+	137.878	31661259
DarkChem	[M-H]-	133.604	31661259
DeepCCS	[M+H]+	132.999	30932474
DeepCCS	[M-H]-	130.231	30932474
DeepCCS	[M-2H]-	166.974	30932474
DeepCCS	[M+Na]+	142.403	30932474
AllCCS	[M+H]+	135.4	32859911
AllCCS	[M+H-H2O]+	131.0	32859911
AllCCS	[M+NH4]+	139.5	32859911
AllCCS	[M+Na]+	140.7	32859911
AllCCS	[M-H]-	131.0	32859911
AllCCS	[M+Na-2H]-	132.0	32859911
AllCCS	[M+HCOO]-	133.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3, 5-Dihydroxyphenylacetic acid	OC(=O)CC1=CC(O)=CC(O)=C1	3405.7	Standard polar	33892256
3, 5-Dihydroxyphenylacetic acid	OC(=O)CC1=CC(O)=CC(O)=C1	1779.7	Standard non polar	33892256
3, 5-Dihydroxyphenylacetic acid	OC(=O)CC1=CC(O)=CC(O)=C1	1881.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3, 5-Dihydroxyphenylacetic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC(O)=CC(O)=C1	1908.1	Semi standard non polar	33892256
3, 5-Dihydroxyphenylacetic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC(CC(=O)O)=C1	1864.5	Semi standard non polar	33892256
3, 5-Dihydroxyphenylacetic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC(O)=CC(O[Si](C)(C)C)=C1	1897.3	Semi standard non polar	33892256
3, 5-Dihydroxyphenylacetic acid,2TMS,isomer #2	C[Si](C)(C)OC1=CC(CC(=O)O)=CC(O[Si](C)(C)C)=C1	1883.6	Semi standard non polar	33892256
3, 5-Dihydroxyphenylacetic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1	1885.8	Semi standard non polar	33892256
3, 5-Dihydroxyphenylacetic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC(O)=CC(O)=C1	2145.5	Semi standard non polar	33892256
3, 5-Dihydroxyphenylacetic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(CC(=O)O)=C1	2109.5	Semi standard non polar	33892256
3, 5-Dihydroxyphenylacetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1	2346.3	Semi standard non polar	33892256
3, 5-Dihydroxyphenylacetic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CC(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C1	2364.2	Semi standard non polar	33892256
3, 5-Dihydroxyphenylacetic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1	2560.3	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-Dihydroxyphenylacetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0900000000-b024ec87cbd249be7bbf	2017-09-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3, 5-Dihydroxyphenylacetic acid GC-MS (3 TMS) - 70eV, Positive	splash10-014i-5092000000-867acbc7281df8f877d1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3, 5-Dihydroxyphenylacetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3, 5-Dihydroxyphenylacetic 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 - 3, 5-Dihydroxyphenylacetic acid 10V, Negative-QTOF	splash10-01b9-0900000000-27369f5ff817ef78d9bb	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3, 5-Dihydroxyphenylacetic acid 20V, Negative-QTOF	splash10-00xs-0900000000-fc50972f0100e0906c40	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3, 5-Dihydroxyphenylacetic acid 40V, Negative-QTOF	splash10-006t-2900000000-5afeb4cf8b516b7fb603	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3, 5-Dihydroxyphenylacetic acid 10V, Positive-QTOF	splash10-0udi-0900000000-06139edcd25f930e5e6a	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3, 5-Dihydroxyphenylacetic acid 20V, Positive-QTOF	splash10-00di-0900000000-24c07570ffa27df663d9	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3, 5-Dihydroxyphenylacetic acid 40V, Positive-QTOF	splash10-00di-2900000000-d84f84c75be435014615	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3, 5-Dihydroxyphenylacetic acid 10V, Positive-QTOF	splash10-00xr-0900000000-564fe5de3eb8ae55265c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3, 5-Dihydroxyphenylacetic acid 20V, Positive-QTOF	splash10-00di-2900000000-465b1ff726ee92f8f52c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3, 5-Dihydroxyphenylacetic acid 40V, Positive-QTOF	splash10-0avr-9600000000-7a011d0e14f32c1f7fa6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3, 5-Dihydroxyphenylacetic acid 10V, Negative-QTOF	splash10-00di-0900000000-ee9e9b8403f62cfc7fdf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3, 5-Dihydroxyphenylacetic acid 20V, Negative-QTOF	splash10-00di-1900000000-45d1604f4f509002f24e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3, 5-Dihydroxyphenylacetic acid 40V, Negative-QTOF	splash10-00r6-9400000000-89c318986817a90906f8	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, D₂O, predicted)	2021-09-25	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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

519640

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

597768

PDB ID

Not Available

ChEBI ID

131431

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

Fa YH, Ni JQ, Wu XJ, Tan JQ, Wu YW: Evaluation of the early response and mechanism of treatment of Parkinson's disease with L-dopa using 18F-fallypride micro-positron emission tomography scanning. Exp Ther Med. 2016 Jan;11(1):101-109. Epub 2015 Nov 27. [PubMed:26889225 ]

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-Dihydroxyphenylacetic acid → 6-[3-(carboxymethyl)-5-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
3, 5-Dihydroxyphenylacetic acid → 6-{[2-(3,5-dihydroxyphenyl)acetyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for 3, 5-Dihydroxyphenylacetic acid (HMDB0094709)

MOL for HMDB0094709 (3, 5-Dihydroxyphenylacetic acid)

3D MOL for HMDB0094709 (3, 5-Dihydroxyphenylacetic acid)

3D SDF for HMDB0094709 (3, 5-Dihydroxyphenylacetic acid)

3D-SDF for HMDB0094709 (3, 5-Dihydroxyphenylacetic acid)

PDB for HMDB0094709 (3, 5-Dihydroxyphenylacetic acid)

3D PDB for HMDB0094709 (3, 5-Dihydroxyphenylacetic acid)

SMILES for HMDB0094709 (3, 5-Dihydroxyphenylacetic acid)

INCHI for HMDB0094709 (3, 5-Dihydroxyphenylacetic acid)

Structure for HMDB0094709 (3, 5-Dihydroxyphenylacetic acid)

3D Structure for HMDB0094709 (3, 5-Dihydroxyphenylacetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions