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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:52 UTC

Update Date

2023-02-21 17:17:15 UTC

HMDB ID

HMDB0006116

Secondary Accession Numbers

HMDB06116

Metabolite Identification

Common Name

3-Hydroxyhippuric acid

Description

3-Hydroxyhippuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. 3-Hydroxyhippuric acid is an organic acid found in normal human urine. 3-Hydroxyhippuric acid is a metabolite of rutin detected in urine after consumption of tomato juice (a source of rutin). 3-Hydroxyhippuric acid has its origin in dietary procyanidins (a major source of polyphenols consisting of elementary flavan-3-ol (epi)catechin units). 3-Hydroxyhippuric acid is a microbial aromatic acid metabolite derived from dietary polyphenols and flavonoids, found in normal human urine (PMID: 12592675 , 2338430 , 17015248 , 14556848 , 12742116 ). It is a marker of gut Clostridium species. Higher levels are associated with higher levels of Clostridia (PMID: 27123458 ).

Structure

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


  Mrv1652309151722382D          

 14 14  0  0  0  0            999 V2000
    1.4289    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
  4 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006116

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CNC(=O)C1=CC=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO4/c11-7-3-1-2-6(4-7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)

> <INCHI_KEY>
XDOFWFNMYJRHEW-UHFFFAOYSA-N

> <FORMULA>
C9H9NO4

> <MOLECULAR_WEIGHT>
195.1721

> <EXACT_MASS>
195.053157781

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.512117298476493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3-hydroxyphenyl)formamido]acetic acid

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
0.2219801626666666

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.826079128411925

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2466748656262534

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4147203141199358

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
48.09860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.91e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxyhippuric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-SEP-17         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.334   5.390   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    7   14                                                  
CONECT    5    8   10                                                       
CONECT    6    1    2    9                                                  
CONECT    7    3    4                                                       
CONECT    8    5   11   12                                                  
CONECT    9    6   10   13                                                  
CONECT   10    5    9                                                       
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14    4                                                            
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
2-[(3-Hydroxyphenyl)formamido]acetic acid	ChEBI
3-Hydroxybenzoylglycine	ChEBI
2-[(3-Hydroxyphenyl)formamido]acetate	Generator
3-Hydroxyhippate	Generator
3-Hydroxyhippic acid	Generator
3-Hydroxyhippurate	HMDB
m-Hydroxyhippurate	HMDB
m-Hydroxyhippuric acid	HMDB
N-m-Hydroxylbenzoylglycine	HMDB
3-Hydroxyhippuric acid	ChEBI
m-Hydroxyhippate	Generator, HMDB
m-Hydroxyhippic acid	Generator, HMDB
2-[(3-Hydroxybenzoyl)amino]acetic acid	HMDB
3'-Hydroxyhippuric acid	HMDB

Chemical Formula

C₉H₉NO₄

Average Molecular Weight

195.1721

Monoisotopic Molecular Weight

195.053157781

IUPAC Name

2-[(3-hydroxyphenyl)formamido]acetic acid

Traditional Name

3-hydroxyhippuric acid

CAS Registry Number

1637-75-8

SMILES

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

InChI Identifier

InChI=1S/C9H9NO4/c11-7-3-1-2-6(4-7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)

InChI Key

XDOFWFNMYJRHEW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hippuric acids

Alternative Parents

Substituents

Hippuric acid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:70824 )
N-acylglycine (CHEBI:70824 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0006116)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006116)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006116)
Feces (PMID: 25037050)

Source

Endogenous

Endogenous (HMDB: HMDB0006116)

Microbe

Microbe (HMDB: HMDB0006116)
Clostridium species (HMDB: HMDB0006116)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0006116)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0006116)

Tea

Tea products (HMDB: HMDB0006116)

Fat and oil

Olive oil (HMDB: HMDB0006116)

Fruit

Fruits (HMDB: HMDB0006116)

Vegetable

Vegetables (HMDB: HMDB0006116)

Legumes (HMDB: HMDB0006116)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0006116)

Nut

Nuts (HMDB: HMDB0006116)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0006116)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0006116)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	164 - 169 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	0.95	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.91 g/L	ALOGPS
logP	0.52	ALOGPS
logP	0.22	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.25	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.1 m³·mol⁻¹	ChemAxon
Polarizability	18.51 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]+	143.675	31661259
DarkChem	[M-H]-	139.186	31661259
DeepCCS	[M+H]+	138.087	30932474
DeepCCS	[M-H]-	135.501	30932474
DeepCCS	[M-2H]-	171.283	30932474
DeepCCS	[M+Na]+	146.151	30932474
AllCCS	[M+H]+	141.8	32859911
AllCCS	[M+H-H2O]+	137.7	32859911
AllCCS	[M+NH4]+	145.6	32859911
AllCCS	[M+Na]+	146.6	32859911
AllCCS	[M-H]-	140.3	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	141.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyhippuric acid	OC(=O)CNC(=O)C1=CC=CC(O)=C1	3234.5	Standard polar	33892256
3-Hydroxyhippuric acid	OC(=O)CNC(=O)C1=CC=CC(O)=C1	2000.7	Standard non polar	33892256
3-Hydroxyhippuric acid	OC(=O)CNC(=O)C1=CC=CC(O)=C1	2176.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyhippuric acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C1=CC=CC(O)=C1	2103.2	Semi standard non polar	33892256
3-Hydroxyhippuric acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC(C(=O)NCC(=O)O)=C1	2077.1	Semi standard non polar	33892256
3-Hydroxyhippuric acid,1TMS,isomer #3	C[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CC(O)=C1	2081.5	Semi standard non polar	33892256
3-Hydroxyhippuric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C1=CC=CC(O[Si](C)(C)C)=C1	2185.7	Semi standard non polar	33892256
3-Hydroxyhippuric acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC(O)=C1)[Si](C)(C)C	2083.4	Semi standard non polar	33892256
3-Hydroxyhippuric acid,2TMS,isomer #3	C[Si](C)(C)OC1=CC=CC(C(=O)N(CC(=O)O)[Si](C)(C)C)=C1	2079.0	Semi standard non polar	33892256
3-Hydroxyhippuric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C	2093.4	Semi standard non polar	33892256
3-Hydroxyhippuric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C	2074.5	Standard non polar	33892256
3-Hydroxyhippuric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C	2209.0	Standard polar	33892256
3-Hydroxyhippuric acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=CC(O)=C1	2352.4	Semi standard non polar	33892256
3-Hydroxyhippuric acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(=O)NCC(=O)O)=C1	2336.3	Semi standard non polar	33892256
3-Hydroxyhippuric acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CC(O)=C1	2347.1	Semi standard non polar	33892256
3-Hydroxyhippuric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2693.8	Semi standard non polar	33892256
3-Hydroxyhippuric acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC(O)=C1)[Si](C)(C)C(C)(C)C	2580.4	Semi standard non polar	33892256
3-Hydroxyhippuric acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)=C1	2598.3	Semi standard non polar	33892256
3-Hydroxyhippuric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2791.5	Semi standard non polar	33892256
3-Hydroxyhippuric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2693.9	Standard non polar	33892256
3-Hydroxyhippuric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2573.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyhippuric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1900000000-49e4d27497eeeff45809	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyhippuric acid GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-7982000000-7959bea2ab616ece8756	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyhippuric 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-Hydroxyhippuric acid 10V, Negative-QTOF	splash10-0udl-1900000000-dc85347d83766215a7b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 20V, Negative-QTOF	splash10-0006-9300000000-4d0f2ba79bccc743efd0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 40V, Negative-QTOF	splash10-0006-9200000000-f1d71d9347520fec146c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 10V, Positive-QTOF	splash10-0002-1900000000-899450f53ef2c1cb3e4b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 20V, Positive-QTOF	splash10-0uk9-4900000000-0ce4cb09039d70fe8e8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 40V, Positive-QTOF	splash10-00fr-9300000000-264f280344785775dc13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 10V, Negative-QTOF	splash10-0006-0900000000-caff5245d469f41c4da8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 20V, Negative-QTOF	splash10-0006-2900000000-8a379c794edd9eeb0a03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 40V, Negative-QTOF	splash10-006x-9300000000-74897c8ed9e9ff09d06b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 10V, Positive-QTOF	splash10-00di-1900000000-c7da1e28001d3b60249f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 20V, Positive-QTOF	splash10-00di-2900000000-cc2fe6c05438067b7def	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 40V, Positive-QTOF	splash10-014l-9100000000-a7e31e4050be2dac0876	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 10V, Negative-QTOF	splash10-0006-7900000000-973fa316a4faa2fb85ec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 20V, Negative-QTOF	splash10-0006-9200000000-feb5bed01fe869d8f260	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyhippuric acid 40V, Negative-QTOF	splash10-0006-9000000000-134764e2910be589b6f9	2021-09-22	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]-)	2023-02-03	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

Cytoplasm (predicted from logP)

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	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 927	19671472	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 927	12592675	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 927	19415668	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 927	17015248	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25762808	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Not Available	22624806	details
Urine	Detected and Quantified	15.06 +/- 10.91 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.51-51.27 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	David F. Putnam C...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 927	19671472	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 927	12592675	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 927	19415668	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 927	17015248	details
Urine	Detected and Quantified	5.7 ± 4.7 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	11368919	details
Urine	Detected and Quantified	1.28 (0.1 - 6.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12592675	details
Urine	Detected and Quantified	2.5 (0.2 -5.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12592675	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21736852	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24390407	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22827565	details
Urine	Detected and Quantified	6.1(4.1-7.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	7.4(5.7-9.1) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	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	Bladder cancer	28157703	details
Urine	Detected and Quantified	19.604 +/- 13.104 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	17.247 +/- 12.596 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	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 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB07069

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023830

KNApSAcK ID

C00052143

Chemspider ID

396603

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

450268

PDB ID

Not Available

ChEBI ID

70824

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Van Brussel, W.; Van Sumere, C. F. N-Acylamino acids and peptides. VI. A simple synthesis of N-acylglycines of the benzoyl and cinnamyl type. Bulletin des Societes Chimiques Belges (1978), 87(10), 791-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. [PubMed:2338430 ]
Rechner AR, Kuhnle G, Hu H, Roedig-Penman A, van den Braak MH, Moore KP, Rice-Evans CA: The metabolism of dietary polyphenols and the relevance to circulating levels of conjugated metabolites. Free Radic Res. 2002 Nov;36(11):1229-41. [PubMed:12592675 ]
Jaganath IB, Mullen W, Edwards CA, Crozier A: The relative contribution of the small and large intestine to the absorption and metabolism of rutin in man. Free Radic Res. 2006 Oct;40(10):1035-46. [PubMed:17015248 ]
Gonthier MP, Donovan JL, Texier O, Felgines C, Remesy C, Scalbert A: Metabolism of dietary procyanidins in rats. Free Radic Biol Med. 2003 Oct 15;35(8):837-44. [PubMed:14556848 ]
Gonthier MP, Rios LY, Verny M, Remesy C, Scalbert A: Novel liquid chromatography-electrospray ionization mass spectrometry method for the quantification in human urine of microbial aromatic acid metabolites derived from dietary polyphenols. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jun 15;789(2):247-55. [PubMed:12742116 ]
Xiong X, Liu D, Wang Y, Zeng T, Peng Y: Urinary 3-(3-Hydroxyphenyl)-3-hydroxypropionic Acid, 3-Hydroxyphenylacetic Acid, and 3-Hydroxyhippuric Acid Are Elevated in Children with Autism Spectrum Disorders. Biomed Res Int. 2016;2016:9485412. doi: 10.1155/2016/9485412. Epub 2016 Mar 30. [PubMed:27123458 ]
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. 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-Hydroxybenzoic acid → 3-Hydroxyhippuric acid	details

Enzyme Details

2. Glycine N-acyltransferase-like protein 1

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:: GLYATL1
Uniprot ID:: Q969I3
Molecular weight:: 35100.895

Enzyme Details

3. Glycine N-acyltransferase-like protein 2

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:: GLYATL2
Uniprot ID:: Q8WU03
Molecular weight:: 34277.055

Enzyme Details

4. Glycine N-acyltransferase-like protein 3

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:: GLYATL3
Uniprot ID:: Q5SZD4
Molecular weight:: 32703.3

Showing metabocard for 3-Hydroxyhippuric acid (HMDB0006116)

MOL for HMDB0006116 (3-Hydroxyhippuric acid)

3D MOL for HMDB0006116 (3-Hydroxyhippuric acid)

3D SDF for HMDB0006116 (3-Hydroxyhippuric acid)

3D-SDF for HMDB0006116 (3-Hydroxyhippuric acid)

PDB for HMDB0006116 (3-Hydroxyhippuric acid)

3D PDB for HMDB0006116 (3-Hydroxyhippuric acid)

SMILES for HMDB0006116 (3-Hydroxyhippuric acid)

INCHI for HMDB0006116 (3-Hydroxyhippuric acid)

Structure for HMDB0006116 (3-Hydroxyhippuric acid)

3D Structure for HMDB0006116 (3-Hydroxyhippuric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions