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Showing metabocard for Phenyllactic acid (HMDB0000779)

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enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:06 UTC
HMDB IDHMDB0000779
Secondary Accession Numbers
  • HMDB00779
Metabolite Identification
Common NamePhenyllactic acid
DescriptionPhenyllactic acid a product of phenylalanine catabolism, appearing prominently in the urine in individuals with phenylketonuria. Levels of several phenylalanine metabolites, including phenylacetate (PAA), phenyllactate (PLA), and phenylpyruvate (PPA)) are elevated in Phenylketonuria (PKU) (OMIM 261600 ). Phenyllactic acid is likely produced from phenylpyruvate via the action of lactate dehydrogenase. The D-form of this organic acid is typically derived from bacterial sources while the L-form is almost certainly endogenous. Levels of phenyllactate are normally very low in blood or urine. High levels of PLA in the urine or blood are often indicative of phenylketonuria (PKU) and hyperphenylalaninemia (HPA). PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid (a precursor of phenylactate). In particular, excessive phenylalanine is typically metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid and then to phenyllactate through the action of lactate dehydrogenase. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation. (PMID: 10790306 ; OMIM: 261600 ). Phenyllactic acid can be found in Acinetobacter, Bacteroides, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas and Staphylococcus (PMID: 19961416 ).
Structure
Data?1582752155
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000779 (Phenyllactic acid)

<string xmlns="http://www.chemspider.com/">
  Mrv1652304222011142D          

 12 12  0  0  1  0            999 V2000
    4.0108   -3.7217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -3.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7732   -3.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -2.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7732   -1.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -0.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -0.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279   -1.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -2.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0108   -2.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334   -2.2950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -1.5836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
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3D MOL for HMDB0000779 (Phenyllactic acid)

HMDB0000779
     RDKit          3D
Phenyllactic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    4.0031    0.0631    0.9509 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1577   -0.0080    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5108    0.3048   -1.2763 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7523   -0.4245    0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5185   -0.7104    1.6094 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8354    0.6814   -0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    0.3357   -0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    0.6558    1.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    0.3345    1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2883   -0.3434    0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6222   -0.6807   -0.8292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2945   -0.3411   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3706    1.2606   -1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -1.3593   -0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -1.5769    1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1273    1.6302    0.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0702    0.8167   -1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428    1.1884    1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1530    0.5885    2.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323   -0.5954    0.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1774   -1.2080   -1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7937   -0.6120   -1.9056 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
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3D SDF for HMDB0000779 (Phenyllactic acid)

<string xmlns="http://www.chemspider.com/">
  Mrv1652304222011142D          

 12 12  0  0  1  0            999 V2000
    4.0108   -3.7217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -3.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7732   -3.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -2.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7732   -1.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -0.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -0.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279   -1.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -2.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0108   -2.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334   -2.2950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -1.5836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000779

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)

> <INCHI_KEY>
VOXXWSYKYCBWHO-UHFFFAOYSA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.1739

> <EXACT_MASS>
166.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.69530388015452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-phenylpropanoic acid

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
1.1844968496666666

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.19195842902614

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.020980916532307

> <JCHEM_PKA_STRONGEST_BASIC>
-3.837374293517553

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
43.458800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-phenyllactic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000779 (Phenyllactic acid)

HMDB0000779
     RDKit          3D
Phenyllactic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    4.0031    0.0631    0.9509 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1577   -0.0080    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5108    0.3048   -1.2763 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7523   -0.4245    0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5185   -0.7104    1.6094 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8354    0.6814   -0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921    0.3357   -0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    0.6558    1.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    0.3345    1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2883   -0.3434    0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6222   -0.6807   -0.8292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2945   -0.3411   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3706    1.2606   -1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -1.3593   -0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -1.5769    1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1273    1.6302    0.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0702    0.8167   -1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428    1.1884    1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1530    0.5885    2.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323   -0.5954    0.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1774   -1.2080   -1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7937   -0.6120   -1.9056 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
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PDB for HMDB0000779 (Phenyllactic acid)

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: <string xmlns="http://www.chemspider.com/">       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  O   UNK     0       7.487  -6.947   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.719  -5.619   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.177  -5.619   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.409  -4.284   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.177  -2.956   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.409  -1.621   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.873  -1.621   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.105  -2.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.873  -4.284   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.487  -4.284   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.022  -4.284   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.719  -2.956   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    4    8                                                       
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0000779 (Phenyllactic acid)

COMPND    HMDB0000779
HETATM    1  O1  UNL     1       4.003   0.063   0.951  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.158  -0.008   0.028  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.511   0.305  -1.276  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.752  -0.424   0.275  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.519  -0.710   1.609  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.835   0.681  -0.221  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.592   0.336  -0.007  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.282   0.656   1.142  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.612   0.335   1.342  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.288  -0.343   0.341  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.622  -0.681  -0.829  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.294  -0.341  -0.989  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.371   1.261  -1.616  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.597  -1.359  -0.297  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.947  -1.577   1.813  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.127   1.630   0.275  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.070   0.817  -1.298  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.743   1.188   1.924  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.153   0.589   2.250  1.00  0.00           H  
HETATM   20  H8  UNL     1      -4.332  -0.595   0.499  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.177  -1.208  -1.589  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.794  -0.612  -1.906  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   16   17
CONECT    7    8    8   12
CONECT    8    9   18
CONECT    9   10   10   19
CONECT   10   11   20
CONECT   11   12   12   21
CONECT   12   22
END
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SMILES for HMDB0000779 (Phenyllactic acid)

OC(CC1=CC=CC=C1)C(O)=O
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INCHI for HMDB0000779 (Phenyllactic acid)

InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-Hydroxy-2-phenylpropionic acidChEBI
2-Phenyllactic acidChEBI
alpha-Hydroxy-alpha-methylbenzeneacetic acidChEBI
alpha-Hydroxy-alpha-phenylpropionic acidChEBI
alpha-Methylmandelic acidChEBI
2-Hydroxy-2-phenylpropionateGenerator
2-PhenyllactateGenerator
a-Hydroxy-a-methylbenzeneacetateGenerator
a-Hydroxy-a-methylbenzeneacetic acidGenerator
alpha-Hydroxy-alpha-methylbenzeneacetateGenerator
Α-hydroxy-α-methylbenzeneacetateGenerator
Α-hydroxy-α-methylbenzeneacetic acidGenerator
a-Hydroxy-a-phenylpropionateGenerator
a-Hydroxy-a-phenylpropionic acidGenerator
alpha-Hydroxy-alpha-phenylpropionateGenerator
Α-hydroxy-α-phenylpropionateGenerator
Α-hydroxy-α-phenylpropionic acidGenerator
a-MethylmandelateGenerator
a-Methylmandelic acidGenerator
alpha-MethylmandelateGenerator
Α-methylmandelateGenerator
Α-methylmandelic acidGenerator
PhenyllactateGenerator
Atrolactic acid, (+-)-isomerMeSH
Hydroxyphenylpropionic acidMeSH
Atrolactic acidMeSH
Atrolactic acid monosodium salt, (S)-isomerMeSH
HMMAMeSH
Hydroxymethylmandelic acidMeSH
2-Hydroxy-3-phenylpropionic acidChEBI
beta-Phenyllactic acidChEBI
DL-3-Phenyllactic acidChEBI
DL-beta-Phenyllactic acidChEBI
2-Hydroxy-3-phenylpropionateGenerator
b-PhenyllactateGenerator
b-Phenyllactic acidGenerator
beta-PhenyllactateGenerator
β-phenyllactateGenerator
β-phenyllactic acidGenerator
DL-3-PhenyllactateGenerator
DL-b-PhenyllactateGenerator
DL-b-Phenyllactic acidGenerator
DL-beta-PhenyllactateGenerator
DL-β-phenyllactateGenerator
DL-β-phenyllactic acidGenerator
3-Phenyllactic acidMeSH, HMDB
3-Phenyllactic acid, monosodium saltMeSH, HMDB
3-PhenyllactateMeSH, Generator, HMDB
3-Phenyllactic acid, calcium saltMeSH, HMDB
3-Phenyllactic acid, (D)-isomerMeSH, HMDB
3-Phenyllactic acid, (DL)-isomerMeSH, HMDB
3-Phenyllactic acid, (L)-isomerMeSH, HMDB
2-Hydroxy-3-(phenyl)propanoic acidHMDB
3-(Phenyl)-2-hydroxypropanoic acidHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name2-hydroxy-3-phenylpropanoic acid
Traditional Nameβ-phenyllactic acid
CAS Registry Number828-01-3
SMILES
OC(CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)
InChI KeyVOXXWSYKYCBWHO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point98 °CNot Available
Boiling Point331.00 °C. @ 332.00 mm Hg (est)The Good Scents Company Information System
Water Solubility64210 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.83HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg134.3630932474
[M-H]-Not Available134.549http://allccs.zhulab.cn/database/detail?ID=AllCCS00000430
[M+H]+Not Available137.91http://allccs.zhulab.cn/database/detail?ID=AllCCS00000430
Predicted Molecular Properties
PropertyValueSource
Water Solubility9.8 g/LALOGPS
logP0.84ALOGPS
logP1.18ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.46 m³·mol⁻¹ChemAxon
Polarizability16.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.25231661259
DarkChem[M-H]-131.1931661259
AllCCS[M+H]+136.53232859911
AllCCS[M-H]-134.31132859911
DeepCCS[M+H]+129.66130932474
DeepCCS[M-H]-125.83330932474
DeepCCS[M-2H]-163.17230932474
DeepCCS[M+Na]+138.67630932474
AllCCS[M+H]+136.532859911
AllCCS[M+H-H2O]+132.232859911
AllCCS[M+NH4]+140.632859911
AllCCS[M+Na]+141.832859911
AllCCS[M-H]-134.332859911
AllCCS[M+Na-2H]-135.332859911
AllCCS[M+HCOO]-136.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.67 minutes32390414
Predicted by Siyang on May 30, 202210.8859 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.53 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid69.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1454.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid344.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid113.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid199.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid103.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid368.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid379.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)117.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid846.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid361.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1034.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid239.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid316.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate399.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA242.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water120.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phenyllactic acidOC(CC1=CC=CC=C1)C(O)=O2893.9Standard polar33892256
Phenyllactic acidOC(CC1=CC=CC=C1)C(O)=O1458.9Standard non polar33892256
Phenyllactic acidOC(CC1=CC=CC=C1)C(O)=O1565.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenyllactic acid,1TMS,isomer #1C[Si](C)(C)OC(CC1=CC=CC=C1)C(=O)O1545.2Semi standard non polar33892256
Phenyllactic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C(O)CC1=CC=CC=C11517.4Semi standard non polar33892256
Phenyllactic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)O[Si](C)(C)C1557.6Semi standard non polar33892256
Phenyllactic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CC1=CC=CC=C1)C(=O)O1768.7Semi standard non polar33892256
Phenyllactic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(O)CC1=CC=CC=C11748.2Semi standard non polar33892256
Phenyllactic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2026.6Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified3.77 +/- 1.71 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.23-0.49 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.23-0.39 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.0680 +/- 0.204 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0.136 +/- 0.476 umol/mmol creatinineInfant (0-1 year old)Both
Normal		 details
UrineDetected and Quantified0.204 +/- 0.612 umol/mmol creatinineInfant (0-1 year old)Both
Normal		 details
UrineDetected and Quantified1.0886 +/- 0.680 umol/mmol creatinineInfant (0-1 year old)Both
Normal		 details
UrineDetected and Quantified1.225 +/- 0.816 umol/mmol creatinineInfant (0-1 year old)Both
Normal		 details
UrineDetected and Quantified1.225 +/- 0.884 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0-82.9 uMChildren (1-13 years old)BothPhenylketonuria details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleSupragingival Plaque details
UrineDetected and Quantified149.7 +/- 208.5 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
UrineDetected and Quantified31.297 +/- 11.566 umol/mmol creatinineChildren (1-13 years old)BothPhenylketonuria details
UrineDetected and Quantified361.277 +/- 500.0731 umol/mmol creatinineChildren (1-13 years old)BothPhenylketonuria details
UrineDetected and Quantified48.306 +/- 24.493 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria		 details
UrineDetected and Quantified59.873 +/- 34.699 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria		 details
UrineDetected and Quantified786.510 +/- 1020.557 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria		 details
UrineDetected and Quantified796.0348 +/- 753.852 umol/mmol creatinineChildren (1-13 years old)Both
Phenylketonuria		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Supragingival Plaque
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Phenylketonuria
  1. Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]
  2. Clemens PC, Schunemann MH, Hoffmann GF, Kohlschutter A: Plasma concentrations of phenyllactic acid in phenylketonuria. J Inherit Metab Dis. 1990;13(2):227-8. [PubMed:2116554 ]
  3. Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB093343
KNApSAcK IDC00000150
Chemspider ID1263
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1303
PDB IDNot Available
ChEBI ID50392
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000250
Good Scents IDNot Available
References
Synthesis ReferenceYu, Jian Ming; Xue, Fen. A method of synthesis of phenyllactic acid and substituted phenyllactic acids. Chinese Chemical Letters (1993), 4(8), 673-4.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Iijima S, Ishii A, Miyakoshi T, Odaira T, Musha M: Studies on the experimental phenylketonuria in rats. Tohoku J Exp Med. 1975 Oct;117(2):167-78. [PubMed:1209606 ]
  2. Sarkissian CN, Scriver CR, Mamer OA: Measurement of phenyllactate, phenylacetate, and phenylpyruvate by negative ion chemical ionization-gas chromatography/mass spectrometry in brain of mouse genetic models of phenylketonuria and non-phenylketonuria hyperphenylalaninemia. Anal Biochem. 2000 May 1;280(2):242-9. [PubMed:10790306 ]
  3. Beloborodova NV, Khodakova AS, Bairamov IT, Olenin AY: Microbial origin of phenylcarboxylic acids in the human body. Biochemistry (Mosc). 2009 Dec;74(12):1350-5. [PubMed:19961416 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details
1. Sulfotransferase family cytosolic 2B member 1
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Phenyllactic acid → 3-phenyl-2-(sulfooxy)propanoic aciddetails
Enzyme Details
2. 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
Phenyllactic acid → 6-(1-carboxy-2-phenylethoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Phenyllactic acid → 3,4,5-trihydroxy-6-[(2-hydroxy-3-phenylpropanoyl)oxy]oxane-2-carboxylic aciddetails