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Showing NP-Card for Hydroxyphenyllactic acid (NP0000341)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:14:44 UTC
NP-MRD IDNP0000341
Secondary Accession NumbersNone
Natural Product Identification
Common NameHydroxyphenyllactic acid
DescriptionHydroxyphenyllactic acid or 4-hydroxyphenyllactate (the L-form) is a tyrosine metabolite. The level of L-hydroxyphenyllactic acid is elevated in patients with a deficiency of the enzyme p-hydroxyphenylpyruvate oxidase (EC 1.14.2.2) (PMID: 4720815 ). L-hydroxyphenyllactate is present in relatively higher concentrations in the cerebrospinal fluid and urine of patients with phenylketonuria (PKU) and tyrosinemia (PMID: 3126358 ). However, the D-form of hydroxyphenyllactate is of bacterial origin and is also found in individuals with bacterial overgrowth or unusual gut microflora (PMID: 3126358 ). Microbial hydroxyphenyllactate is likely derived from phenolic or polyphenolic compounds in the diet. Bifidobacteria and lactobacilli produce considerable amounts of phenyllactic and p-hydroxyphenyllactic acids (PMID: 23061754 ). It has also been shown that hydroxyphenyllactate decreases ROS (reactive oxygen species) production in both mitochondria and neutrophils and so hydroxyphenyllactate may function as a natural anti-oxidant (PMID: 23061754 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000341 (Hydroxyphenyllactic acid)

<string xmlns="http://www.chemspider.com/">
  Mrv1652304222011122D          

 13 13  0  0  1  0            999 V2000
    5.1418   -2.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8388   -0.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5409   -2.0060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5619   -3.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029   -2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418   -2.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4298   -1.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8388   -1.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908   -1.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739   -2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908   -3.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  8  2  0  0  0  0
  3  8  1  0  0  0  0
  4 11  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
Download

3D MOL for NP0000341 (Hydroxyphenyllactic acid)

HMDB0000755
     RDKit          3D
Hydroxyphenyllactic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.7562    0.9097    0.8438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3688    0.6644   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2309    1.7735   -1.1626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0443   -0.6829   -0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950   -0.6359   -2.1771 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0319   -1.3252    0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2598   -0.6943    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226    0.1796    1.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6488    0.8181    1.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297    0.6146    0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    1.2322    0.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5351   -0.2698   -0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502   -0.9023   -0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0953    2.0252   -1.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757   -1.2826   -0.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4858   -0.5543   -2.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8441   -2.3705   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748   -1.4996    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479    0.4116    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908    1.5049    2.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1183    2.1229    0.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3525   -0.4590   -1.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1929   -1.5805   -1.4460 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
 10 12  1  0
 12 13  2  0
 13  7  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

3D SDF for NP0000341 (Hydroxyphenyllactic acid)

<string xmlns="http://www.chemspider.com/">
  Mrv1652304222011122D          

 13 13  0  0  1  0            999 V2000
    5.1418   -2.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8388   -0.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5409   -2.0060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5619   -3.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029   -2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418   -2.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4298   -1.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8388   -1.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908   -1.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739   -2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908   -3.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  8  2  0  0  0  0
  3  8  1  0  0  0  0
  4 11  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000341

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)

> <INCHI_KEY>
JVGVDSSUAVXRDY-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.508950163763846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-(4-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.8809315280000001

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.50382828900583

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5839647995095922

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8298154633716104

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
45.439700000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyphenyllactic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000341 (Hydroxyphenyllactic acid)

HMDB0000755
     RDKit          3D
Hydroxyphenyllactic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.7562    0.9097    0.8438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3688    0.6644   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2309    1.7735   -1.1626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0443   -0.6829   -0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950   -0.6359   -2.1771 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0319   -1.3252    0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2598   -0.6943    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226    0.1796    1.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6488    0.8181    1.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297    0.6146    0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    1.2322    0.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5351   -0.2698   -0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502   -0.9023   -0.6363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0953    2.0252   -1.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757   -1.2826   -0.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4858   -0.5543   -2.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8441   -2.3705   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748   -1.4996    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479    0.4116    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908    1.5049    2.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1183    2.1229    0.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3525   -0.4590   -1.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1929   -1.5805   -1.4460 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
 10 12  1  0
 12 13  2  0
 13  7  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

PDB for NP0000341 (Hydroxyphenyllactic 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       9.598  -5.297   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.899  -1.449   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.210  -3.745   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.916  -6.068   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.912  -3.754   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.598  -3.745   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.269  -2.973   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.899  -2.992   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.583  -2.992   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.912  -5.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.245  -5.297   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.245  -3.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.583  -6.068   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    8                                                            
CONECT    3    8                                                            
CONECT    4   11                                                            
CONECT    5    7    9   10                                                  
CONECT    6    1    7    8                                                  
CONECT    7    5    6                                                       
CONECT    8    2    3    6                                                  
CONECT    9    5   12                                                       
CONECT   10    5   13                                                       
CONECT   11    4   12   13                                                  
CONECT   12    9   11                                                       
CONECT   13   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for NP0000341 (Hydroxyphenyllactic acid)

COMPND    HMDB0000755
HETATM    1  O1  UNL     1       2.756   0.910   0.844  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.369   0.664  -0.302  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.231   1.774  -1.163  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.044  -0.683  -0.831  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.695  -0.636  -2.177  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.032  -1.325   0.035  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.260  -0.694   0.204  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.423   0.180   1.268  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.649   0.818   1.470  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.730   0.615   0.641  1.00  0.00           C  
HETATM   11  O4  UNL     1      -3.950   1.232   0.818  1.00  0.00           O  
HETATM   12  C8  UNL     1      -2.535  -0.270  -0.421  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.350  -0.902  -0.636  1.00  0.00           C  
HETATM   14  H1  UNL     1       3.095   2.025  -1.645  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.976  -1.283  -0.780  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.486  -0.554  -2.761  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.844  -2.370  -0.357  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.475  -1.500   1.044  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.348   0.412   1.982  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.791   1.505   2.299  1.00  0.00           H  
HETATM   21  H8  UNL     1      -4.118   2.123   0.370  1.00  0.00           H  
HETATM   22  H9  UNL     1      -3.352  -0.459  -1.094  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.193  -1.581  -1.446  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5    6   15
CONECT    5   16
CONECT    6    7   17   18
CONECT    7    8    8   13
CONECT    8    9   19
CONECT    9   10   10   20
CONECT   10   11   12
CONECT   11   21
CONECT   12   13   13   22
CONECT   13   23
END
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SMILES for NP0000341 (Hydroxyphenyllactic acid)

OC(CC1=CC=C(O)C=C1)C(O)=O
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INCHI for NP0000341 (Hydroxyphenyllactic acid)

InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
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View in JSmol
Synonyms
ValueSource
2-Hydroxy-3-(4-hydroxyphenyl)propanoateChEBI
2-Hydroxy-3-(p-hydroxyphenyl)propionic acidChEBI
4-Hydroxyphenyllactic acidChEBI
beta-(4-Hydroxyphenyl)lactic acidChEBI
beta-(p-Hydroxyphenyl)lactic acidChEBI
DL-p-Hydroxyphenyllactic acidChEBI
p-Hydroxyphenyl lactic acidChEBI
4-HydroxyphenyllactateKegg
p-HydroxyphenyllactateKegg
2-Hydroxy-3-(4-hydroxyphenyl)propanoic acidGenerator
2-Hydroxy-3-(p-hydroxyphenyl)propionateGenerator
b-(4-Hydroxyphenyl)lactateGenerator
b-(4-Hydroxyphenyl)lactic acidGenerator
beta-(4-Hydroxyphenyl)lactateGenerator
Β-(4-hydroxyphenyl)lactateGenerator
Β-(4-hydroxyphenyl)lactic acidGenerator
b-(p-Hydroxyphenyl)lactateGenerator
b-(p-Hydroxyphenyl)lactic acidGenerator
beta-(p-Hydroxyphenyl)lactateGenerator
Β-(p-hydroxyphenyl)lactateGenerator
Β-(p-hydroxyphenyl)lactic acidGenerator
DL-p-HydroxyphenyllactateGenerator
p-Hydroxyphenyl lactateGenerator
p-Hydroxyphenyllactic acidGenerator
HydroxyphenyllactateGenerator
(RS)-3-(4-Hydroxyphenyl)lactateHMDB
(RS)-3-(4-Hydroxyphenyl)lactic acidHMDB
3-(4-Hydroxyphenyl)-DL-lactateHMDB
3-(4-Hydroxyphenyl)-DL-lactic acidHMDB
3-(4-Hydroxyphenyl)lactateHMDB
3-(p-Hydroxyphenyl)-lactateHMDB
3-(p-Hydroxyphenyl)-lactic acidHMDB
a,4-DihydroxybenzenepropanoateHMDB
a,4-Dihydroxybenzenepropanoic acidHMDB
b-(p-Hydroxyphenyl)-DL-lactateHMDB
b-(p-Hydroxyphenyl)-DL-lactic acidHMDB
beta-(p-Hydroxyphenyl)-DL-lactateHMDB
beta-(p-Hydroxyphenyl)-DL-lactic acidHMDB
DL-3-(4-Hydroxyphenyl)lactateHMDB
DL-3-(4-Hydroxyphenyl)lactic acidHMDB
HPLAHMDB
4-Hydroxyphenyllactic acid, (DL)-isomerHMDB
Para-hydroxyphenyllactic acidHMDB
2-HydroxyphloretateHMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acidHMDB
3-(4-Hydroxyphenyl)lactic acidHMDB, Generator, MeSH
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid HMDB
2-Hydroxy-3-(4-hydroxyphenyl)propionic acid
3-(4-Hydroxyphenyl)-2-hydroxypropanoic acid
3-(4'-Hydroxyphenyl)-2-hydroxypropionic acid
3-(4'-Hydroxyphenyl)lactic acid
Chemical FormulaC9H10O4
Average Mass182.1733 Da
Monoisotopic Mass182.05791 Da
IUPAC Name2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
Traditional Namehydroxyphenyllactic acid
CAS Registry Number306-23-0
SMILES
OC(CC1=CC=C(O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
InChI KeyJVGVDSSUAVXRDY-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Grosmannia huntiiLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pseudo-nitzschia multistriataLOTUS Database
Pterocarpus marsupiumLOTUS Database
Salmonella entericaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
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
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility12.9 mg/mL at 16 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.79 g/LALOGPS
logP0.87ALOGPS
logP0.88ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.58ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.44 m³·mol⁻¹ChemAxon
Polarizability17.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000755
DrugBank IDNot Available
Phenol Explorer Compound ID577
FoodDB IDFDB019021
KNApSAcK IDC00050491
Chemspider ID9010
KEGG Compound IDC03672
BioCyc ID4-HYDROXYPHENYLLACTATE
BiGG ID2392410
Wikipedia LinkNot Available
METLIN ID5723
PubChem Compound9378
PDB IDNot Available
ChEBI ID17385
Good Scents IDrw1622271
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  3. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
  4. Bennett MJ, Ragni MC, Hood I, Hale DE: Comparison of post-mortem urinary and vitreous humour organic acids. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):541-5. [PubMed:1444166 ]
  5. Roth K, Cohn R, Yandrasitz J, Preti G, Dodd P, Segal S: Beta-methylcrotonic aciduria associated with lactic acidosis. J Pediatr. 1976 Feb;88(2):229-35. [PubMed:1249684 ]
  6. Spaapen LJ, Ketting D, Wadman SK, Bruinvis L, Duran M: Urinary D-4-hydroxyphenyllactate, D-phenyllactate and D-2-hydroxyisocaproate, abnormalities of bacterial origin. J Inherit Metab Dis. 1987;10(4):383-90. [PubMed:3126358 ]
  7. Deutsch JC: Determination of p-hydroxyphenylpyruvate, p-hydroxyphenyllactate and tyrosine in normal human plasma by gas chromatography-mass spectrometry isotope-dilution assay. J Chromatogr B Biomed Sci Appl. 1997 Mar 7;690(1-2):1-6. [PubMed:9106023 ]
  8. Mrochek JE, Dinsmore SR, Ohrt DW: Monitoring phenylalanine-tyrosine metabolism by high-resolution liquid chromatography of urine. Clin Chem. 1973 Aug;19(8):927-36. [PubMed:4720815 ]
  9. Higa S, Kishimoto S: Isolation of 2-hydroxycarboxylic acids with a boronate affinity gel. Anal Biochem. 1986 Apr;154(1):71-4. [PubMed:3706738 ]
  10. Jakobs C, Sweetman L, Nyhan WL: Chemical analysis of succinylacetone and 4-hydroxyphenyllactate in amniotic fluid using selective ion monitoring. Prenat Diagn. 1984 May-Jun;4(3):187-94. [PubMed:6463026 ]
  11. Beloborodova N, Bairamov I, Olenin A, Shubina V, Teplova V, Fedotcheva N: Effect of phenolic acids of microbial origin on production of reactive oxygen species in mitochondria and neutrophils. J Biomed Sci. 2012 Oct 12;19:89. doi: 10.1186/1423-0127-19-89. [PubMed:23061754 ]
  12. (). Charles Scriver, Arthur Beaudet, William Sly, David Valle, Barton Childs, Kenneth Kinzler, Bert Vogelstein. The Metabolic and Molecular Bases of Inherited Disease. McGraw-Hill Professional; 8 edition (Dec 15 2000). . . [ISBN:978-0079130358 ]