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Showing NP-Card for Ortho-Hydroxyphenylacetic acid (NP0001331)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:47 UTC
NP-MRD IDNP0001331
Secondary Accession NumbersNone
Natural Product Identification
Common NameOrtho-Hydroxyphenylacetic acid
DescriptionOrtho-hydroxyphenylacetic acid, also known as (o-hydroxyphenyl)acetate or 2-hydroxybenzeneacetic acid, is a member of the class of compounds known as 2(hydroxyphenyl)acetic acids. 2(Hydroxyphenyl)acetic acids are phenylacetic acids that carry a hydroxyl group at the 2-position. Ortho-hydroxyphenylacetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Ortho-hydroxyphenylacetic acid can be found in a number of food items such as natal plum, lemon verbena, half-highbush blueberry, and parsley, which makes ortho-hydroxyphenylacetic acid a potential biomarker for the consumption of these food products. Ortho-hydroxyphenylacetic acid can be found primarily in blood, feces, and urine. Moreover, ortho-hydroxyphenylacetic acid is found to be associated with phenylketonuria, which is an inborn error of metabolism. Ortho-Hydroxyphenylacetic acid is a substrate of the enzyme oxidoreductases (EC 1.14.13.-) In the pathway styrene degradation (KEGG).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001331 (Ortho-Hydroxyphenylacetic acid)

      
  Mrv1652305271900242D          

 11 11  0  0  0  0            999 V2000
   -0.0430   -1.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7574   -1.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -1.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -3.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0430   -2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -0.5977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714   -1.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3858   -1.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859   -2.6601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003   -1.4226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
Download

3D MOL for NP0001331 (Ortho-Hydroxyphenylacetic acid)

HMDB0000669
     RDKit          3D
ortho-Hydroxyphenylacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.8407   -1.0859   -0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -0.1613   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663    0.0120   -0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3365    0.6509    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0528    0.1973    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7572   -0.5702    1.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0502   -0.9881    1.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7017   -0.6577   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    0.1085   -1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6989    0.5297   -0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0279    1.2955   -1.7110 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2040   -0.1365   -0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    1.7119    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    0.4723    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2274   -0.8195    2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595   -1.5844    1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7075   -0.9601   -0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130    0.3755   -1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    1.6100   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0001331 (Ortho-Hydroxyphenylacetic acid)

      
  Mrv1652305271900242D          

 11 11  0  0  0  0            999 V2000
   -0.0430   -1.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7574   -1.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -1.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -3.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0430   -2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -0.5977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714   -1.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3858   -1.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859   -2.6601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003   -1.4226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001331

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC1=C(O)C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4,9H,5H2,(H,10,11)

> <INCHI_KEY>
CCVYRRGZDBSHFU-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.606132955958135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
1.3074287836666667

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.3788850306351

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.00071468776261

> <JCHEM_PKA_STRONGEST_BASIC>
-6.017511950103068

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
39.3465

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
o-hydroxyphenylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001331 (Ortho-Hydroxyphenylacetic acid)

HMDB0000669
     RDKit          3D
ortho-Hydroxyphenylacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.8407   -1.0859   -0.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -0.1613   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663    0.0120   -0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3365    0.6509    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0528    0.1973    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7572   -0.5702    1.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0502   -0.9881    1.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7017   -0.6577   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    0.1085   -1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6989    0.5297   -0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0279    1.2955   -1.7110 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2040   -0.1365   -0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4917    1.7119    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    0.4723    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2274   -0.8195    2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5595   -1.5844    1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7075   -0.9601   -0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130    0.3755   -1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    1.6100   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
Download

PDB for NP0001331 (Ortho-Hydroxyphenylacetic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.080  -3.426   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.414  -2.656   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.748  -3.426   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.748  -4.966   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.414  -5.736   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.080  -4.966   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.414  -1.116   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.253  -2.656   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.587  -3.426   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.587  -4.966   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.921  -2.656   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0001331 (Ortho-Hydroxyphenylacetic acid)

COMPND    HMDB0000669
HETATM    1  O1  UNL     1       1.841  -1.086  -0.883  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.300  -0.161  -0.139  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.666   0.012  -0.123  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.337   0.651   0.648  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.053   0.197   0.395  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.757  -0.570   1.308  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.050  -0.988   1.065  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.702  -0.658  -0.105  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.011   0.108  -1.027  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.699   0.530  -0.774  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.028   1.296  -1.711  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.204  -0.136  -0.971  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.492   1.712   0.393  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.557   0.472   1.742  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.227  -0.820   2.221  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.560  -1.584   1.807  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.707  -0.960  -0.338  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.513   0.375  -1.951  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.912   1.610  -1.557  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6    6   10
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9   17
CONECT    9   10   10   18
CONECT   10   11
CONECT   11   19
END
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SMILES for NP0001331 (Ortho-Hydroxyphenylacetic acid)

OC(=O)CC1=C(O)C=CC=C1
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INCHI for NP0001331 (Ortho-Hydroxyphenylacetic acid)

InChI=1S/C8H8O3/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
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View in JSmol
Synonyms
ValueSource
(O-Hydroxyphenyl)acetic acidChEBI
2'-Hydroxyphenylacetic acidChEBI
2-Hydroxybenzeneacetic acidChEBI
2-Hydroxyphenylacetic acidChEBI
O-Hydroxyphenylacetic acidChEBI
(O-Hydroxyphenyl)acetateGenerator
2'-HydroxyphenylacetateGenerator
2-HydroxybenzeneacetateGenerator
2-HydroxyphenylacetateGenerator
O-HydroxyphenylacetateGenerator
Ortho-hydroxyphenylacetateGenerator
(2-Hydroxyphenyl)acetateHMDB
(2-Hydroxyphenyl)acetic acidHMDB
(O-Hydroxyphenyl)-acetateHMDB
(O-Hydroxyphenyl)-acetic acidHMDB
2-HPAAHMDB
HydroxyphenylacetateHMDB
Hydroxyphenylacetic acidHMDB
O-Hydroxyphenyl acetic acidHMDB
Ortho-hydroxyphenylacetic acidMeSH
alpha-Hydroxy phenylacetic acidMeSH
Chemical FormulaC8H8O3
Average Mass152.1473 Da
Monoisotopic Mass152.04734 Da
IUPAC Name2-(2-hydroxyphenyl)acetic acid
Traditional Nameo-hydroxyphenylacetic acid
CAS Registry Number614-75-5
SMILES
OC(=O)CC1=C(O)C=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
InChI KeyCCVYRRGZDBSHFU-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)V.dorna832021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Astilbe chinensisLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Grosmannia crassivaginataLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
Oenothera elataLOTUS Database
OryctolagusFooDB
Ovis ariesFooDB
Penicillium chrysogenumLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Pinus montanaLOTUS Database
Secamone afzeliiLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Theobroma cacaoFooDB
Tragopogon orientalisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acids
Direct Parent2(hydroxyphenyl)acetic acids
Alternative Parents
Substituents
  • 2(hydroxyphenyl)acetic acid
  • 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
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point145 - 147 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility44 mg/mLNot Available
LogP0.85Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility6.38 g/LALOGPS
logP0.99ALOGPS
logP1.31ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.35 m³·mol⁻¹ChemAxon
Polarizability14.61 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000669
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030339
KNApSAcK IDNot Available
Chemspider ID11476
KEGG Compound IDC05852
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5639
PubChem Compound11970
PDB IDNot Available
ChEBI ID28478
Good Scents IDrw1176931
References
General References
  1. Watson DG, McGhee CN, Midgley JM, Zhou P, Doig WM: Determination of acidic metabolites of biogenic amines in human aqueous humour by gas chromatography--negative ion chemical ionisation mass spectrometry. J Neurochem. 1992 Jan;58(1):116-20. [PubMed:1727423 ]
  2. Greenslade D, Havler ME, Humphrey MJ, Jordan BJ, Rance MJ: Species differences in the metabolism and excretion of fenclofenac. Xenobiotica. 1980 Oct;10(10):753-60. [PubMed:7456491 ]
  3. Jones MR, Kopple JD, Swendseid ME: Phenylalanine metabolism in uremic and normal man. Kidney Int. 1978 Aug;14(2):169-79. [PubMed:357810 ]
  4. Langenbeck U, Behbehani A, Mench-Hoinowski A, Petersen M: Absence of a significant renal threshold for two aromatic acids in phenylketonuric children over two years of age. Eur J Pediatr. 1980 Aug;134(2):115-8. [PubMed:7439195 ]
  5. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]