Showing metabocard for Phenyllactic acid (MMDBc0000543)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:40:10 UTC
Update Date2024-04-30 19:32:56 UTC
Metabolite IDMMDBc0000543
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb588ab750>

<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 #<Metabolite:0x00007fdb588ab750>

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 #<Metabolite:0x00007fdb588ab750>

<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>
MMDBc0000543

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007fdb588ab750>

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 #<Metabolite:0x00007fdb588ab750>

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 #<Metabolite:0x00007fdb588ab750>

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 #<Metabolite:0x00007fdb588ab750>

OC(CC1=CC=CC=C1)C(O)=O
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INCHI for #<Metabolite:0x00007fdb588ab750>

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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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
Molecular FormulaC9H10O3
Average Mass166.1739
Monoisotopic Mass166.062994186
IUPAC Name2-hydroxy-3-phenylpropanoic acid
Traditional Nameβ-phenyllactic acid
CAS Registry NumberNot Available
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