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Showing NP-Card for Phenyllactic acid (NP0001402)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:56 UTC
NP-MRD IDNP0001402
Secondary Accession NumbersNone
Natural Product 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 .
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001402 (Phenyllactic acid)

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

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

3D MOL for NP0001402 (Phenyllactic acid)

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

3D SDF for NP0001402 (Phenyllactic acid)

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

 12 12  0  0  1  0            999 V2000
    4.0108   -3.7217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -3.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7732   -3.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -2.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7732   -1.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -0.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -0.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279   -1.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -2.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0108   -2.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334   -2.2950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -1.5836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001402

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0001402 (Phenyllactic acid)

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

PDB for NP0001402 (Phenyllactic acid)

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: <string xmlns="http://www.chemspider.com/">       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  O   UNK     0       7.487  -6.947   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.719  -5.619   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.177  -5.619   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.409  -4.284   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.177  -2.956   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.409  -1.621   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.873  -1.621   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.105  -2.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.873  -4.284   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.487  -4.284   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.022  -4.284   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.719  -2.956   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    4    8                                                       
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for NP0001402 (Phenyllactic acid)

COMPND    HMDB0000779
HETATM    1  O1  UNL     1       4.003   0.063   0.951  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.158  -0.008   0.028  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.511   0.305  -1.276  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.752  -0.424   0.275  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.519  -0.710   1.609  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.835   0.681  -0.221  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.592   0.336  -0.007  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.282   0.656   1.142  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.612   0.335   1.342  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.288  -0.343   0.341  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.622  -0.681  -0.829  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.294  -0.341  -0.989  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.371   1.261  -1.616  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.597  -1.359  -0.297  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.947  -1.577   1.813  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.127   1.630   0.275  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.070   0.817  -1.298  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.743   1.188   1.924  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.153   0.589   2.250  1.00  0.00           H  
HETATM   20  H8  UNL     1      -4.332  -0.595   0.499  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.177  -1.208  -1.589  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.794  -0.612  -1.906  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    6   14
CONECT    5   15
CONECT    6    7   16   17
CONECT    7    8    8   12
CONECT    8    9   18
CONECT    9   10   10   19
CONECT   10   11   20
CONECT   11   12   12   21
CONECT   12   22
END
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SMILES for NP0001402 (Phenyllactic acid)

OC(CC1=CC=CC=C1)C(O)=O
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INCHI for NP0001402 (Phenyllactic acid)

InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)
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View in JSmol
Synonyms
ValueSource
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
PhenyllactateGenerator
3-Phenyllactic acidHMDB
3-Phenyllactic acid, monosodium saltHMDB
3-PhenyllactateHMDB
3-Phenyllactic acid, calcium saltHMDB
3-Phenyllactic acid, (D)-isomerHMDB
3-Phenyllactic acid, (DL)-isomerHMDB
3-Phenyllactic acid, (L)-isomerHMDB
2-Hydroxy-3-(phenyl)propanoic acidHMDB
3-(Phenyl)-2-hydroxypropanoic acidHMDB
3-(Phenyl)-2-hydroxypropionic acid
3-(Phenyl)lactic acid
Chemical FormulaC9H10O3
Average Mass166.1739 Da
Monoisotopic Mass166.06299 Da
IUPAC Name2-hydroxy-3-phenylpropanoic acid
Traditional Nameβ-phenyllactic acid
CAS Registry Number828-01-3
SMILES
OC(CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)
InChI KeyVOXXWSYKYCBWHO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 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
Anisodus acutangulusPlant
Anisodus belladonnaPlant
Anser anserFooDB
Anthocercis fasciculataPlant
Anthocercis myoporoidesPlant
Anthocercis pannosaPlant
Anthocercis viscosaPlant
Anthocercis walcottiiPlant
Aruncus dioicusLOTUS Database
Atropa belladonnaPlant
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brugmansia arboreaPlant
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Corydalis yanhusuoPlant
Cyphanthera anthocercideaPlant
Cyphomandra betaceaePlant
Datura metelPlant
Datura stramoniumPlant
Dromaius novaehollandiaeFooDB
Duboisia arenitensisPlant
Duboisia leichhardtiiPlant
Duboisia myoporoidesPlant
Equus caballusFooDB
Euphorbia petiolataLOTUS Database
Gallus gallusFooDB
Grosmannia huntiiLOTUS Database
Hyoscyamus nigerPlant
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Mandragora autunnalePlant
Mandragora vernalisPlant
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Przewalkia tangutica-
Rosa taiwanensisLOTUS Database
Secale cerealeLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Lactobacillus plantarum MiLAB 393KNApSAcK 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
  • 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point98 °CNot Available
Boiling Point331.00 °C. @ 332.00 mm Hg (est)The Good Scents Company Information System
Water Solubility64210 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.83Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted 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
HMDB IDHMDB0000779
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022236
KNApSAcK IDC00000150
Chemspider ID3715
KEGG Compound IDC01479
BioCyc IDCPD-7999
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5745
PubChem Compound3848
PDB IDNot Available
ChEBI ID25998
Good Scents IDrw1622301
References
General References
  1. Iijima S, Ishii A, Miyakoshi T, Odaira T, Musha M: Studies on the experimental phenylketonuria in rats. Tohoku J Exp Med. 1975 Oct;117(2):167-78. [PubMed:1209606 ]
  2. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
  3. Sarkissian CN, Scriver CR, Mamer OA: Measurement of phenyllactate, phenylacetate, and phenylpyruvate by negative ion chemical ionization-gas chromatography/mass spectrometry in brain of mouse genetic models of phenylketonuria and non-phenylketonuria hyperphenylalaninemia. Anal Biochem. 2000 May 1;280(2):242-9. [PubMed:10790306 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  5. Beloborodova NV, Khodakova AS, Bairamov IT, Olenin AY: Microbial origin of phenylcarboxylic acids in the human body. Biochemistry (Mosc). 2009 Dec;74(12):1350-5. doi: 10.1134/s0006297909120086. [PubMed:19961416 ]