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Showing metabocard for L-3-Phenyllactic acid (HMDB0000748)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:00:08 UTC
HMDB IDHMDB0000748
Secondary Accession Numbers
  • HMDB0000475
  • HMDB00475
  • HMDB00748
Metabolite Identification
Common NameL-3-Phenyllactic acid
DescriptionL-3-Phenyllactic acid (or PLA) is a chiral aromatic compound involved in phenylalanine metabolism. It 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.
Structure
Data?1582752154
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000748 (L-3-Phenyllactic acid)


  Mrv1652305271900172D          

 12 12  0  0  1  0            999 V2000
   16.9991   -7.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4115   -6.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9991   -5.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1741   -5.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7616   -6.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1741   -7.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7616   -5.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9366   -5.0284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.5242   -4.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9366   -3.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6992   -4.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5242   -5.7430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  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
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  1  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
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3D MOL for HMDB0000748 (L-3-Phenyllactic acid)

HMDB0000748
     RDKit          3D
L-3-Phenyllactic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.3523    1.2013   -0.9886 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0139    0.6526    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9396    0.0305    0.8812 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925    0.6753    0.5093 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4462    0.0117    1.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092   -0.1097   -0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6332   -0.1555   -0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1441   -1.1720    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4830   -1.2555    0.9047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515   -0.2742    0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310    0.7427   -0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956    0.8269   -0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2966   -0.9105    0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2196    1.7223    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -0.1155    2.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9771    0.3759   -1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544   -1.1321   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4257   -1.9189    0.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535   -2.0571    1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3977   -0.2765    0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5166    1.5094   -0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0805    1.6287   -1.2997 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  1
  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
Download

3D SDF for HMDB0000748 (L-3-Phenyllactic acid)


  Mrv1652305271900172D          

 12 12  0  0  1  0            999 V2000
   16.9991   -7.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4115   -6.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9991   -5.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1741   -5.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7616   -6.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1741   -7.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7616   -5.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9366   -5.0284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.5242   -4.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9366   -3.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6992   -4.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5242   -5.7430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  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
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  1  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000748

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H](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)/t8-/m1/s1

> <INCHI_KEY>
VOXXWSYKYCBWHO-MRVPVSSYSA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.1739

> <EXACT_MASS>
166.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.726051670425765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-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>
(R)-phenyllactate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000748 (L-3-Phenyllactic acid)

HMDB0000748
     RDKit          3D
L-3-Phenyllactic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.3523    1.2013   -0.9886 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0139    0.6526    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9396    0.0305    0.8812 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925    0.6753    0.5093 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4462    0.0117    1.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092   -0.1097   -0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6332   -0.1555   -0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1441   -1.1720    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4830   -1.2555    0.9047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515   -0.2742    0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310    0.7427   -0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956    0.8269   -0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2966   -0.9105    0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2196    1.7223    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -0.1155    2.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9771    0.3759   -1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544   -1.1321   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4257   -1.9189    0.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535   -2.0571    1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3977   -0.2765    0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5166    1.5094   -0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0805    1.6287   -1.2997 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  1
  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 HMDB0000748 (L-3-Phenyllactic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      31.732 -13.388   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.501 -12.054   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.732 -10.720   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.192 -10.720   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.422 -12.054   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.192 -13.388   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.422  -9.386   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.882  -9.386   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.112  -8.054   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      27.882  -6.720   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      25.572  -8.054   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      27.112 -10.720   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0000748 (L-3-Phenyllactic acid)

COMPND    HMDB0000748
HETATM    1  O1  UNL     1       3.352   1.201  -0.989  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.014   0.653   0.087  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.940   0.030   0.881  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.593   0.675   0.509  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.446   0.012   1.725  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.809  -0.110  -0.519  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.633  -0.155  -0.200  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.144  -1.172   0.581  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.483  -1.255   0.905  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.351  -0.274   0.424  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.831   0.743  -0.358  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.496   0.827  -0.682  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.297  -0.910   0.680  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.220   1.722   0.591  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.311  -0.115   2.183  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.977   0.376  -1.492  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.254  -1.132  -0.553  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.426  -1.919   0.935  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.853  -2.057   1.513  1.00  0.00           H  
HETATM   20  H8  UNL     1      -4.398  -0.277   0.635  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.517   1.509  -0.732  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.080   1.629  -1.300  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 HMDB0000748 (L-3-Phenyllactic acid)

O[C@H](CC1=CC=CC=C1)C(O)=O
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INCHI for HMDB0000748 (L-3-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)/t8-/m1/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(R)-PhenyllactateChEBI
D-3-Phenyllactic acidChEBI
(R)-3-(Phenyl)lactateKegg
(R)-Phenyllactic acidGenerator
D-3-PhenyllactateGenerator
(R)-3-(Phenyl)lactic acidGenerator
L-3-PhenyllactateGenerator
(-)-2-Hydroxy-3-phenylpropanoateHMDB
(-)-2-Hydroxy-3-phenylpropanoic acidHMDB
(-)-2-Hydroxy-3-phenylpropionateHMDB
(-)-2-Hydroxy-3-phenylpropionic acidHMDB
(-)-3-PhenyllactateHMDB
(-)-3-Phenyllactic acidHMDB
(-)-b-PhenyllactateHMDB
(-)-b-Phenyllactic acidHMDB
(-)-beta-PhenyllactateHMDB
(-)-beta-Phenyllactic acidHMDB
(2S)-2-Hydroxy-3-phenylpropanoateHMDB
(2S)-2-Hydroxy-3-phenylpropanoic acidHMDB
(2S)-2-Hydroxy-3-phenylpropionateHMDB
(2S)-2-Hydroxy-3-phenylpropionic acidHMDB
(S)-3-Phenyl-lactateHMDB
(S)-3-Phenyl-lactic acidHMDB
(S)-3-Phenyllactic acidHMDB
(S)-a-Hydroxy-benzenepropanoateHMDB
(S)-a-Hydroxy-benzenepropanoic acidHMDB
(S)-alpha-Hydroxy-benzenepropanoateHMDB
(S)-alpha-Hydroxy-benzenepropanoic acidHMDB
(S)-b-PhenyllacticHMDB
(S)-beta-PhenyllacticHMDB
alpha-Hydroxy-beta-phenyl-propionic acidHMDB
HFAHMDB
L-(-)-3-Phenyllactic acidHMDB
L-2-Hydroxy-3-phenyl-propionic acidHMDB
L-beta-Phenyllactic acidHMDB
L-Phenyl lactateHMDB
Phenyllactic acidHMDB
(R)-3-PhenyllactateHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name(2R)-2-hydroxy-3-phenylpropanoic acid
Traditional Name(R)-phenyllactate
CAS Registry Number20312-36-1
SMILES
O[C@H](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)/t8-/m1/s1
InChI KeyVOXXWSYKYCBWHO-MRVPVSSYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Benzenoid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point121 - 125 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
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
Polarizability16.73 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]+137.29631661259
DarkChem[M-H]-135.46431661259
AllCCS[M+H]+136.53232859911
AllCCS[M-H]-134.31132859911
DeepCCS[M+H]+132.89230932474
DeepCCS[M-H]-129.52630932474
DeepCCS[M-2H]-166.74330932474
DeepCCS[M+Na]+142.28130932474
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
L-3-Phenyllactic acidO[C@H](CC1=CC=CC=C1)C(O)=O2854.0Standard polar33892256
L-3-Phenyllactic acidO[C@H](CC1=CC=CC=C1)C(O)=O1466.5Standard non polar33892256
L-3-Phenyllactic acidO[C@H](CC1=CC=CC=C1)C(O)=O1528.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-3-Phenyllactic acid,1TMS,isomer #1C[Si](C)(C)O[C@H](CC1=CC=CC=C1)C(=O)O1550.2Semi standard non polar33892256
L-3-Phenyllactic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](O)CC1=CC=CC=C11500.3Semi standard non polar33892256
L-3-Phenyllactic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](CC1=CC=CC=C1)O[Si](C)(C)C1570.0Semi standard non polar33892256
L-3-Phenyllactic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](CC1=CC=CC=C1)C(=O)O1783.8Semi standard non polar33892256
L-3-Phenyllactic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)CC1=CC=CC=C11738.6Semi standard non polar33892256
L-3-Phenyllactic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2043.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - L-3-Phenyllactic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0007-0910000000-ee61dd1edcb64a1158352014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-3-Phenyllactic acid EI-B (Non-derivatized)splash10-0007-0920000000-7efa1766fa6121c5f6952017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-3-Phenyllactic acid GC-EI-TOF (Non-derivatized)splash10-0007-0910000000-ee61dd1edcb64a1158352017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-750e52d0df9e2b90be092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9540000000-c06e2865c7cf1c780f112017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-0900000000-c20feab32f47edc5bb942012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0f89-9500000000-598d564a5c5cb5a6febb2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0ac0-9000000000-32b5f6f43141f16996a42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Positive-QTOFsplash10-0kmi-1900000000-9df5ce396877a246e75a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Positive-QTOFsplash10-0ufr-5900000000-3ebebc6c015723d2e26d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Positive-QTOFsplash10-014i-0900000000-09797df3a57ff3212fae2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Positive-QTOFsplash10-004i-9000000000-55faf2887a4699d775df2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Negative-QTOFsplash10-002f-9000000000-5e9184f3d8f3a1c84cb52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Negative-QTOFsplash10-014i-1900000000-2173c51c5d8f4369c56a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Positive-QTOFsplash10-014r-1900000000-30445b1c1ad4ff6c6cfe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Positive-QTOFsplash10-014i-0900000000-68f9968ec4336192e0932021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Negative-QTOFsplash10-00mo-9400000000-3fc7b7dbdcdb0c24a7182021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Positive-QTOFsplash10-00ke-1900000000-b4165543fe4077bc88782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Positive-QTOFsplash10-006y-4900000000-9cc77ecfa0e908d400f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Positive-QTOFsplash10-0006-9100000000-8e08ba85783d44c725b82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Negative-QTOFsplash10-014i-0900000000-c5b01c647718505d882a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Negative-QTOFsplash10-01bd-2900000000-2cd5c47ea7b35f76e87b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Negative-QTOFsplash10-00mo-9300000000-22457d19a65466f8e94d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Positive-QTOFsplash10-00dl-5900000000-eb26ccce0382619681682021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Positive-QTOFsplash10-0006-9300000000-aa44337c740dacf05e9c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Positive-QTOFsplash10-0006-9100000000-6509f4478fff1766b65a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Negative-QTOFsplash10-014i-3900000000-15a50bcc903d54af3f432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Negative-QTOFsplash10-0006-9400000000-0d7b49d15700ae2666452021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Negative-QTOFsplash10-0006-9300000000-ca99933d289067e5347a2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified0.427 +/- 0.354 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.596 +/- 0.337 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years 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)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Phenylketonuria
  1. 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 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022220
KNApSAcK IDC00000150
Chemspider ID558480
KEGG Compound IDC05607
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound643327
PDB IDNot Available
ChEBI ID32978
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tekewe A, Singh S, Singh M, Mohan U, Banerjee UC: Development and validation of HPLC method for the resolution of drug intermediates: DL-3-Phenyllactic acid, DL-O-acetyl-3-phenyllactic acid and (+/-)-mexiletine acetamide enantiomers. Talanta. 2008 Mar 15;75(1):239-45. doi: 10.1016/j.talanta.2007.11.004. Epub 2007 Nov 13. [PubMed:18371874 ]
  2. (). Andrew D. Abell, John W. Blunt, Glenn J. Foulds and Murray H. G. Munro Chemistry of the mycalamides: antiviral and antitumour compounds from a New Zealand marine sponge. Part 6.1–3 The synthesis and testing of analogues of the C(7)–C(10) fragment. J. Chem. Soc., Perkin Trans. 1, 1997, 1647 - 1654,. .