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Showing metabocard for D-Phenyllactic acid (HMDB0000563)

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enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:57 UTC
HMDB IDHMDB0000563
Secondary Accession Numbers
  • HMDB00563
Metabolite Identification
Common NameD-Phenyllactic acid
DescriptionD-Phenyllactic acid, also known as L-3-phenyllactate, 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. D-Phenyllactic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1676999697
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000563 (D-Phenyllactic acid)

HFA
  Mrv1652304062012592D          

 13 13  0  0  0  0            999 V2000
   -0.1575    1.2268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.8143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2714    1.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714    2.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575   -0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575   -1.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -1.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -1.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859    0.8143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    1.3983    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2 13  1  1  0  0  0
  3  4  2  0  0  0  0
  3 12  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  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
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3D MOL for HMDB0000563 (D-Phenyllactic acid)

HMDB0000563
     RDKit          3D
D-Phenyllactic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.7578   -1.3663   -0.1406 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1033   -0.3151   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029    0.8945    0.0216 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6902   -0.3628   -0.6594 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3532   -1.6991   -0.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8674    0.2410    0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5612    0.2909    0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3136   -0.7903    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6686   -0.8577    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3453    0.1712   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229    1.2614   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2593    1.3192   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8143    1.2929    0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6264    0.1727   -1.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8836   -2.2287   -0.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2271    1.2905    0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752   -0.3095    1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8249   -1.6501    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2200   -1.7373    0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4199    0.1538   -0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1618    2.0641   -0.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7040    2.1647   -0.7234 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  6
  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 HMDB0000563 (D-Phenyllactic acid)

HFA
  Mrv1652304062012592D          

 13 13  0  0  0  0            999 V2000
   -0.1575    1.2268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.8143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2714    1.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714    2.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575   -0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575   -1.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -1.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -1.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859    0.8143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    1.3983    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2 13  1  1  0  0  0
  3  4  2  0  0  0  0
  3 12  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  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>
HMDB0000563

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](O)(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-/m0/s1

> <INCHI_KEY>
VOXXWSYKYCBWHO-QMMMGPOBSA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.1739

> <EXACT_MASS>
166.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.69614539230921

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-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>
43.45880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-3-phenyllactic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000563 (D-Phenyllactic acid)

HMDB0000563
     RDKit          3D
D-Phenyllactic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.7578   -1.3663   -0.1406 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1033   -0.3151   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029    0.8945    0.0216 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6902   -0.3628   -0.6594 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3532   -1.6991   -0.8622 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8674    0.2410    0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5612    0.2909    0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3136   -0.7903    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6686   -0.8577    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3453    0.1712   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229    1.2614   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2593    1.3192   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8143    1.2929    0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6264    0.1727   -1.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8836   -2.2287   -0.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2271    1.2905    0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752   -0.3095    1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8249   -1.6501    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2200   -1.7373    0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4199    0.1538   -0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1618    2.0641   -0.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7040    2.1647   -0.7234 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  6
  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 HMDB0000563 (D-Phenyllactic acid)

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HFA                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  O   UNK     0      -0.294   2.290   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.040   1.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.373   2.290   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.373   3.830   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.040  -0.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.294  -0.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.294  -2.330   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.628  -0.020   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.628  -3.100   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.961  -0.790   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.961  -2.330   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.707   1.520   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       1.040   2.610   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    5   13                                             
CONECT    3    2    4   12                                                  
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    3                                                            
CONECT   13    2                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0000563 (D-Phenyllactic acid)

COMPND    HMDB0000563
HETATM    1  O1  UNL     1       3.758  -1.366  -0.141  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.103  -0.315  -0.247  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.703   0.894   0.022  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.690  -0.363  -0.659  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.353  -1.699  -0.862  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.867   0.241   0.423  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.561   0.291   0.212  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.314  -0.790   0.642  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.669  -0.858   0.498  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.345   0.171  -0.094  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.623   1.261  -0.533  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.259   1.319  -0.382  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.814   1.293   0.940  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.626   0.173  -1.627  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.884  -2.229  -0.215  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.227   1.290   0.622  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.075  -0.309   1.364  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.825  -1.650   1.127  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.220  -1.737   0.856  1.00  0.00           H  
HETATM   20  H8  UNL     1      -4.420   0.154  -0.226  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.162   2.064  -0.996  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.704   2.165  -0.723  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 HMDB0000563 (D-Phenyllactic acid)

[H][C@](O)(CC1=CC=CC=C1)C(O)=O
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INCHI for HMDB0000563 (D-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-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
ALPHA-HYDROXY-BETA-phenyl-propionIC ACIDChEBI
L-(-)-3-Phenyllactic acidChEBI
L-3-Phenyllactic acidChEBI
L-beta-Phenyllactic acidChEBI
a-HYDROXY-b-phenyl-propionateGenerator
a-HYDROXY-b-phenyl-propionic acidGenerator
alpha-HYDROXY-beta-phenyl-propionateGenerator
Α-hydroxy-β-phenyl-propionateGenerator
Α-hydroxy-β-phenyl-propionic acidGenerator
L-(-)-3-PhenyllactateGenerator
L-3-PhenyllactateGenerator
L-b-PhenyllactateGenerator
L-b-Phenyllactic acidGenerator
L-beta-PhenyllactateGenerator
L-Β-phenyllactateGenerator
L-Β-phenyllactic acidGenerator
D-PhenyllactateGenerator
(+)-2-Hydroxy-3-phenylpropionateHMDB
(+)-2-Hydroxy-3-phenylpropionic acidHMDB
(+)-3-PhenyllactateHMDB
(+)-3-Phenyllactic acidHMDB
(+)-b-PhenyllactateHMDB
(+)-b-Phenyllactic acidHMDB
(+)-beta-PhenyllactateHMDB
(+)-beta-Phenyllactic acidHMDB
(2R)-2-Hydroxy-2-phenylpropanoateHMDB
(2R)-2-Hydroxy-2-phenylpropanoic acidHMDB
(2R)-2-Hydroxy-2-phenylpropionateHMDB
(2R)-2-Hydroxy-2-phenylpropionic acidHMDB
(R)-2-Hydroxy-2-phenylpropionateHMDB
(R)-2-Hydroxy-2-phenylpropionic acidHMDB
(R)-2-Phenyl-2-hydroxypropanoateHMDB
(R)-2-Phenyl-2-hydroxypropanoic acidHMDB
(R)-3-Phenyl-lactateHMDB
(R)-3-Phenyl-lactic acidHMDB
(R)-3-PhenyllactateHMDB
(R)-3-Phenyllactic acidHMDB
(R)-a-Hydroxy-3-phenylpropionateHMDB
(R)-a-Hydroxy-3-phenylpropionic acidHMDB
(R)-a-Hydroxy-benzenepropanoateHMDB
(R)-a-Hydroxy-benzenepropanoic acidHMDB
(R)-alpha-Hydroxy-3-phenylpropionateHMDB
(R)-alpha-Hydroxy-3-phenylpropionic acidHMDB
(R)-alpha-Hydroxy-benzenepropanoateHMDB
(R)-alpha-Hydroxy-benzenepropanoic acidHMDB
(R)-b-PhenyllactateHMDB
(R)-b-Phenyllactic acidHMDB
(R)-beta-PhenyllactateHMDB
(R)-beta-Phenyllactic acidHMDB
(R)-PhenyllactateHMDB
(R)-Phenyllactic acidHMDB
b-Phenyl-D-lactateHMDB
b-Phenyl-D-lactic acidHMDB
beta-Phenyl-delta-lactateHMDB
beta-Phenyl-delta-lactic acidHMDB
D-2-Hydroxy-3-phenylpropionateHMDB
D-2-Hydroxy-3-phenylpropionic acidHMDB
D-3-PhenyllactateHMDB
D-3-Phenyllactic acidHMDB
D-b-PhenyllactateHMDB
D-b-Phenyllactic acidHMDB
delta-2-Hydroxy-3-phenylpropionateHMDB
delta-2-Hydroxy-3-phenylpropionic acidHMDB
delta-3-PhenyllactateHMDB
delta-3-Phenyllactic acidHMDB
delta-beta-PhenyllactateHMDB
delta-beta-Phenyllactic acidHMDB
delta-PhenyllactateHMDB
delta-Phenyllactic acidHMDB
(S)-3-PhenyllactateHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name(2S)-2-hydroxy-3-phenylpropanoic acid
Traditional NameL-3-phenyllactic acid
CAS Registry Number7326-19-4
SMILES
[H][C@](O)(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-/m0/s1
InChI KeyVOXXWSYKYCBWHO-QMMMGPOBSA-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 Point122-124 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.184Not 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
Polarizability16.7 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]+136.67731661259
DarkChem[M-H]-134.92231661259
AllCCS[M+H]+136.56332859911
AllCCS[M-H]-134.31132859911
DeepCCS[M+H]+131.49130932474
DeepCCS[M-H]-129.15530932474
DeepCCS[M-2H]-164.69830932474
DeepCCS[M+Na]+139.15630932474
AllCCS[M+H]+136.632859911
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
D-Phenyllactic acid[H][C@](O)(CC1=CC=CC=C1)C(O)=O2854.0Standard polar33892256
D-Phenyllactic acid[H][C@](O)(CC1=CC=CC=C1)C(O)=O1466.5Standard non polar33892256
D-Phenyllactic acid[H][C@](O)(CC1=CC=CC=C1)C(O)=O1528.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Phenyllactic acid,1TMS,isomer #1C[Si](C)(C)O[C@@H](CC1=CC=CC=C1)C(=O)O1550.2Semi standard non polar33892256
D-Phenyllactic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](O)CC1=CC=CC=C11500.3Semi standard non polar33892256
D-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
D-Phenyllactic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H](CC1=CC=CC=C1)C(=O)O1783.8Semi standard non polar33892256
D-Phenyllactic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](O)CC1=CC=CC=C11738.6Semi standard non polar33892256
D-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 - D-Phenyllactic acid EI-B (Non-derivatized)splash10-0006-9100000000-c22a5f17e7fecfb666f22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Phenyllactic acid EI-B (Non-derivatized)splash10-0006-9100000000-c22a5f17e7fecfb666f22018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-750e52d0df9e2b90be092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9540000000-c06e2865c7cf1c780f112017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Phenyllactic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-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 - D-Phenyllactic acid 35V, Negative-QTOFsplash10-0gb9-1900000000-cc48c5ff57b37ce10c092021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 10V, Positive-QTOFsplash10-01bd-2900000000-92cd31ed8e8e8e87180f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 20V, Positive-QTOFsplash10-006x-5900000000-d1b1e4fdbfd8306c92652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 40V, Positive-QTOFsplash10-0006-9100000000-750584951bb8866056f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 10V, Negative-QTOFsplash10-014i-2900000000-1f4cdc94d5bb4ac6489e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 20V, Negative-QTOFsplash10-01bc-6900000000-779d8af9b71dee9ffe5a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 40V, Negative-QTOFsplash10-004l-9300000000-bb0139bf3ea8e3c03d202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 10V, Positive-QTOFsplash10-00dl-5900000000-eb26ccce0382619681682021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 20V, Positive-QTOFsplash10-0006-9300000000-aa44337c740dacf05e9c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 40V, Positive-QTOFsplash10-0006-9100000000-6509f4478fff1766b65a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 10V, Negative-QTOFsplash10-014i-3900000000-15a50bcc903d54af3f432021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 20V, Negative-QTOFsplash10-0006-9400000000-0d7b49d15700ae2666452021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Phenyllactic acid 40V, Negative-QTOFsplash10-0006-9300000000-ca99933d289067e5347a2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
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 IDDB02494
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05607
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5547
PubChem Compound444718
PDB IDNot Available
ChEBI ID43065
Food Biomarker OntologyNot Available
VMH IDPLAC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKamata, Masahiro; Toyomasu, Ryuta; Suzuki, Eiichiro; Tanaka, Takashi. D-Phenyllactic acid production by Brevibacterium or Corynebacterium. Jpn. Kokai Tokkyo Koho (1986), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

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
D-Phenyllactic acid → (2S)-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
D-Phenyllactic acid → 6-[(1R)-1-carboxy-2-phenylethoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
D-Phenyllactic acid → 3,4,5-trihydroxy-6-{[(2S)-2-hydroxy-3-phenylpropanoyl]oxy}oxane-2-carboxylic aciddetails