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Showing NP-Card for 3-Hydroxymandelic acid (NP0000523)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-16 18:04:07 UTC
NP-MRD IDNP0000523
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxymandelic acid
Description3-Hydroxymandelic acid, also known as m-hydroxymandelate or MHMA, is a 2-hydroxy monocarboxylic acid. 3-Hydroxymandelic acid is the dehydroxylated (positions 2 and 3’) derivative of phenylacetic acid. It is a white crystalline solid that is soluble in water and polar organic solvents. It derives from a mandelic acid. Mandelic acid is a substrate or product of several biochemical processes called the mandelate pathway. Mandelate racemase interconverts the two enantiomers via a pathway that involves cleavage of the alpha-CH bond. Mandelate dehydrogenase is yet another enzyme on this pathway. Mandelate also arises from trans-cinnamate via phenylacetic acid, which is hydroxylated. Derivatives of mandelic acid, such as 3-hydroxymandelic acid, are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-O-methyl transferase.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000523 (3-Hydroxymandelic acid)

<string xmlns="http://www.chemspider.com/">86957
  Mrv1652304222010582D          

 12 12  0  0  1  0            999 V2000
    3.0179    1.1862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3034   -1.7013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468    2.0113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1613    0.7738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324   -0.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324    0.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0179   -0.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -0.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0179   -1.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -1.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468    1.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3 12  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0000523 (3-Hydroxymandelic acid)

HMDB0000750
     RDKit          3D
3-Hydroxymandelic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.0542   -1.4537    1.4990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.8883    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0151   -1.6012   -0.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177    0.4456    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    1.0010   -1.0496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396    0.3920    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304    1.5768   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.5244   -0.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5025    0.3660   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8438   -0.7727    0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4813   -1.9856    0.4118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -0.7621    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9508   -1.9163   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9259    1.1488    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    1.3719   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    2.5017   -0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3345    2.4460   -0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5905    0.3197   -0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716   -2.0242    0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -1.6899    0.5367 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0000523 (3-Hydroxymandelic acid)

<string xmlns="http://www.chemspider.com/">86957
  Mrv1652304222010582D          

 12 12  0  0  1  0            999 V2000
    3.0179    1.1862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3034   -1.7013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468    2.0113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1613    0.7738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324   -0.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324    0.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0179   -0.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -0.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0179   -1.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -1.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468    1.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3 12  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000523

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
OLSDAJRAVOVKLG-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.549898712046303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2-(3-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
0.5922703229999999

> <ALOGPS_LOGS>
-1.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.370825435875659

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.303530000093164

> <JCHEM_PKA_STRONGEST_BASIC>
-4.132531240571596

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
40.6847

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
MHMA

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000523 (3-Hydroxymandelic acid)

HMDB0000750
     RDKit          3D
3-Hydroxymandelic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.0542   -1.4537    1.4990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.8883    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0151   -1.6012   -0.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177    0.4456    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    1.0010   -1.0496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396    0.3920    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304    1.5768   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.5244   -0.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5025    0.3660   -0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8438   -0.7727    0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4813   -1.9856    0.4118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -0.7621    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9508   -1.9163   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9259    1.1488    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    1.3719   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    2.5017   -0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3345    2.4460   -0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5905    0.3197   -0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716   -2.0242    0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -1.6899    0.5367 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

PDB for NP0000523 (3-Hydroxymandelic acid)

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: <string xmlns="http://www.chemspider.com/">86957  
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  O   UNK     0       5.633   2.214   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.300  -3.176   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.301   3.754   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.634   1.444   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.967  -0.096   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.967   1.444   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.633  -0.866   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.301  -0.866   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.633  -2.406   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.301  -2.406   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.967  -3.176   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.301   2.214   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5    6    7    8                                                  
CONECT    6    1    5   12                                                  
CONECT    7    5    9                                                       
CONECT    8    5   10                                                       
CONECT    9    2    7   11                                                  
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    3    4    6                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
Download

3D PDB for NP0000523 (3-Hydroxymandelic acid)

COMPND    HMDB0000750
HETATM    1  O1  UNL     1      -2.054  -1.454   1.499  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.263  -0.888   0.393  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.015  -1.601  -0.533  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.718   0.446   0.157  1.00  0.00           C  
HETATM    5  O3  UNL     1      -2.181   1.001  -1.050  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.240   0.392   0.066  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.430   1.577  -0.269  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.799   1.524  -0.367  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.503   0.366  -0.148  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.844  -0.773   0.175  1.00  0.00           C  
HETATM   11  O4  UNL     1       2.481  -1.986   0.412  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.463  -0.762   0.283  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.951  -1.916  -0.324  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.926   1.149   1.000  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.405   1.372  -1.523  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.116   2.502  -0.443  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.335   2.446  -0.629  1.00  0.00           H  
HETATM   18  H6  UNL     1       3.590   0.320  -0.225  1.00  0.00           H  
HETATM   19  H7  UNL     1       3.472  -2.024   0.341  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.047  -1.690   0.537  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    6   14
CONECT    5   15
CONECT    6    7    7   12
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10   18
CONECT   10   11   12   12
CONECT   11   19
CONECT   12   20
END
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SMILES for NP0000523 (3-Hydroxymandelic acid)

OC(C(O)=O)C1=CC(O)=CC=C1
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INCHI for NP0000523 (3-Hydroxymandelic acid)

InChI=1S/C8H8O4/c9-6-3-1-2-5(4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
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View in JSmol
Synonyms
ValueSource
2-Hydroxy-2-(3-hydroxyphenyl)acetic acidChEBI
2-Hydroxy-2-(3-hydroxyphenyl)ethanoic acidChEBI
m-Hydroxymandelic acidChEBI
2-Hydroxy-2-(3-hydroxyphenyl)acetateGenerator
2-Hydroxy-2-(3-hydroxyphenyl)ethanoateGenerator
m-HydroxymandelateGenerator
3-HydroxymandelateGenerator
3-Hydroxyphenylglycolic acidHMDB
alpha,3-Dihydroxybenzeneacetic acidHMDB
DL-3-HydroxymandelateHMDB
DL-3-Hydroxymandelic acidHMDB
DL-Hydroxy(m-hydroxyphenyl)acetic acidHMDB
Hydroxy(3-hydroxyphenyl)acetic acidHMDB
m-Hydroxy-(6ci,7ci,8ci)mandelateHMDB
m-Hydroxy-(6ci,7ci,8ci)mandelic acidHMDB
Meta-hydroxymandelic acidHMDB
MHMAHMDB
2-Hydroxy-2-(3'-hydroxyphenyl)acetic acidHMDB
(3-Hydroxyphenyl)-2-hydroxyacetic acid
(3-Hydroxyphenyl)-2-hydroxyethanoic acid
Chemical FormulaC8H8O4
Average Mass168.1467 Da
Monoisotopic Mass168.04226 Da
IUPAC Name2-hydroxy-2-(3-hydroxyphenyl)acetic acid
Traditional NameMHMA
CAS Registry Number17119-15-2
SMILES
OC(C(O)=O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C8H8O4/c9-6-3-1-2-5(4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
InChI KeyOLSDAJRAVOVKLG-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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 NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-09View Spectrum
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
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
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-4-unsubstituted benzenoids
Direct Parent1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility31 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.5 g/LALOGPS
logP0.89ALOGPS
logP0.59ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.68 m³·mol⁻¹ChemAxon
Polarizability15.55 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000750
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022222
KNApSAcK IDNot Available
Chemspider ID78444
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Hydroxymandelic acid
METLIN ID732
PubChem Compound86957
PDB IDNot Available
ChEBI ID86553
Good Scents IDNot Available
References
General References
  1. Midgley JM, Couch MW, Crowley JR, Williams CM: Identification and quantitative determination of o- and m-hydroxymandelic acid in human urine. Biomed Mass Spectrom. 1979 Nov;6(11):485-90. [PubMed:534686 ]
  2. Ibrahim KE, Midgley JM, Crowley JR, Williams CM: The mammalian metabolism of R-(-)-m-synephrine. J Pharm Pharmacol. 1983 Mar;35(3):144-7. [PubMed:6132969 ]
  3. Gumbhir K, Mason WD: Determination of m-hydroxymandelic acid, m-hydroxyphenylglycol and their conjugates in human plasma using liquid chromatography with electrochemical detection. J Pharm Biomed Anal. 1994 Jul;12(7):943-9. [PubMed:7981325 ]
  4. Crowley JR, Couch MW, Williams CM, Threatte RM, Fregly MJ: Normal excretion of m-hydroxymandelic acid in hypertensive patients. Clin Chim Acta. 1981 Jan 22;109(2):125-31. [PubMed:7471493 ]
  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 ]