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Showing NP-Card for 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid (NP0000841)

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Record Information
Version2.0
Created at2006-05-22 14:18:00 UTC
Updated at2021-06-29 00:47:36 UTC
NP-MRD IDNP0000841
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
Description3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid (HPHPA) is an organic acid detected in human urine. It is relatively abundant in adult human urine and it is normally relatively benign. It is thought that the presence of this acid is from nutritional sources (i.E. Dietary phenylalanine or polyphenols). However, there has been a considerable degree of ambiguity in the origin and/or significance of this compound (PMID: 11978597 ). Recently, it has been reported that HPHPA is actually an abnormal phenylalanine metabolite arising from bacterial metabolism in the gastrointestinal tract. Specifically, HPHPA appears to arise from the action of the anaerobic bacteria Clostridia sp. (PMID: 20423563 ; PMID: 24063620 ). Elevated levels of HPHPA have been reported in the urine of children with autism as well as in adult patients with schizophrenia. It has been proposed that HPHPA may be a bacterial metabolite of m-tyrosine, a tyrosine analog that causes symptoms of autism in experimental animals. Under certain conditions, HPHPA can act as a neurotoxin and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of HPHPA are associated with autism and schizophrenia. The mechanism by which HPHPA exerts its toxic effects is not clear. It may function as a catecholamine analog and disrupt catecholamine signalling, especially in younger individuals. Alternately, HPHPA may function as an amino acid analog to tyrosine and phenylalanine. High plasma concentrations of phenylalanine (and possibly HPHPA) are known to influence the blood-brain barrier transport of large neutral amino acids. This altered transport is believed to interfere with the function of different cerebral enzyme systems in the developing brain. Studies have shown that higher levels of HPHPA are associated with overgrowth of Clostridia in the gut, including Clostridium difficile, Clostridium sporogenes, Clostridium botulinum, Clostridium calortolerans, Clostridium mangenoyi, Clostridium ghoni, Clostridium bifermentans, Clostridium sordelli. (PMID: 20423563 ; PMID: 24063620 )
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000841 (3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid)


  Mrv1652305261923562D          

 13 13  0  0  0  0            999 V2000
10000.346510000.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0613 9999.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.776110000.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.4888 9999.9804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.776110001.2163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.346510001.2163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.491110000.3923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6337 9999.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.919210000.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2047 9999.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2046 9999.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9191 9998.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6337 9999.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
 10  7  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
Download

3D MOL for NP0000841 (3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid)

HMDB0002643
     RDKit          3D
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
   -1.0096    0.9563    1.8240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0185    0.8085    1.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0122    1.7880    1.2835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1733   -0.2731    0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0194   -1.2248    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461   -2.1733   -0.9424 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752   -0.5657   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5733   -0.0699   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7832    0.5330   -1.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7530    0.6733   -0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4665    0.1831    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4324    0.3170    1.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2475   -0.4256    0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7265    1.5440    1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4550    0.0966   -0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583   -0.8833    0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9572   -1.7724    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351   -1.7491   -1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1887   -0.1804   -2.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194    0.9220   -2.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7056    1.1502   -1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4589    1.1381    2.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0850   -0.7924    1.7078 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
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13  7  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

3D SDF for NP0000841 (3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid)


  Mrv1652305261923562D          

 13 13  0  0  0  0            999 V2000
10000.346510000.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0613 9999.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.776110000.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.4888 9999.9804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.776110001.2163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.346510001.2163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.491110000.3923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6337 9999.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.919210000.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2047 9999.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2046 9999.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9191 9998.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6337 9999.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
 10  7  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000841

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
KHTAGVZHYUZYMF-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.308563596160983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.68

> <JCHEM_LOGP>
0.677093841666667

> <ALOGPS_LOGS>
-1.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.366546387463833

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9429308279967894

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1637676884793553

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
45.30900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mhpha

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000841 (3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid)

HMDB0002643
     RDKit          3D
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
   -1.0096    0.9563    1.8240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0185    0.8085    1.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0122    1.7880    1.2835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1733   -0.2731    0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0194   -1.2248    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461   -2.1733   -0.9424 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752   -0.5657   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5733   -0.0699   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7832    0.5330   -1.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7530    0.6733   -0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4665    0.1831    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4324    0.3170    1.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2475   -0.4256    0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7265    1.5440    1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4550    0.0966   -0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583   -0.8833    0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9572   -1.7724    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351   -1.7491   -1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1887   -0.1804   -2.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194    0.9220   -2.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7056    1.1502   -1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4589    1.1381    2.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0850   -0.7924    1.7078 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
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13  7  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

PDB for NP0000841 (3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0    8667.3138667.399   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.6488666.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.9828667.399   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8671.3128666.630   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.9828668.937   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8667.3138668.937   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8661.9838667.399   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8665.9838666.631   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.6498667.401   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3158666.631   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.3158665.091   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.6498664.321   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.9838665.091   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1                                                            
CONECT    7   10                                                            
CONECT    8    9   13    1                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    7                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for NP0000841 (3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid)

COMPND    HMDB0002643
HETATM    1  O1  UNL     1      -1.010   0.956   1.824  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.018   0.808   1.088  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.012   1.788   1.283  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.173  -0.273   0.108  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.019  -1.225   0.033  1.00  0.00           C  
HETATM    6  O3  UNL     1      -1.346  -2.173  -0.942  1.00  0.00           O  
HETATM    7  C4  UNL     1       0.275  -0.566  -0.270  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.573  -0.070  -1.528  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.783   0.533  -1.788  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.753   0.673  -0.817  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.467   0.183   0.438  1.00  0.00           C  
HETATM   12  O4  UNL     1       3.432   0.317   1.425  1.00  0.00           O  
HETATM   13  C9  UNL     1       1.247  -0.426   0.704  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.726   1.544   1.961  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.455   0.097  -0.906  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.058  -0.883   0.440  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.957  -1.772   0.994  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.835  -1.749  -1.686  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.189  -0.180  -2.289  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.019   0.922  -2.771  1.00  0.00           H  
HETATM   21  H8  UNL     1       3.706   1.150  -1.029  1.00  0.00           H  
HETATM   22  H9  UNL     1       3.459   1.138   2.019  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.085  -0.792   1.708  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6    7   17
CONECT    6   18
CONECT    7    8    8   13
CONECT    8    9   19
CONECT    9   10   10   20
CONECT   10   11   21
CONECT   11   12   13   13
CONECT   12   22
CONECT   13   23
END
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SMILES for NP0000841 (3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid)

OC(CC(O)=O)C1=CC(O)=CC=C1
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INCHI for NP0000841 (3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid)

InChI=1S/C9H10O4/c10-7-3-1-2-6(4-7)8(11)5-9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
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View in JSmol
Synonyms
ValueSource
(3-Hydroxyphenyl)hydracrylic acidChEBI
3'-Hydroxyphenylhydracrylic acidChEBI
3-(3-Hydroxyphenyl)-3-hydroxypropionic acidChEBI
3-(3-Hydroxyphenyl)hydracrylic acidChEBI
3-(m-Hydroxyphenyl)hydracrylic acidChEBI
3-Hydroxy-3-(3-hydroxyphenyl)propionic acidChEBI
3-Hydroxyphenyl-hydracrylic acidChEBI
b-(m-Hydroxyphenyl)hydracrylic acidChEBI
beta-(m-Hydroxyphenyl)hydracrylic acidChEBI
HPHPAChEBI
(3-Hydroxyphenyl)hydracrylateGenerator
3'-HydroxyphenylhydracrylateGenerator
3-(3-Hydroxyphenyl)-3-hydroxypropionateGenerator
3-(3-Hydroxyphenyl)hydracrylateGenerator
3-(m-Hydroxyphenyl)hydracrylateGenerator
3-Hydroxy-3-(3-hydroxyphenyl)propionateGenerator
3-Hydroxyphenyl-hydracrylateGenerator
b-(m-Hydroxyphenyl)hydracrylateGenerator
beta-(m-Hydroxyphenyl)hydracrylateGenerator
Β-(m-hydroxyphenyl)hydracrylateGenerator
Β-(m-hydroxyphenyl)hydracrylic acidGenerator
3-(3-Hydroxyphenyl)-3-hydroxypropanoateGenerator
HPHPA CPDHMDB
beta-(Meta-hydroxyphenyl)hydracrylic acidHMDB
MHPHAHMDB
3-Hydroxy-3-(3'-hydroxyphenyl)propanoic acidHMDB
3-Hydroxy-3-(3-hydroxyphenyl)propanoic acidHMDB
3-(3'-Hydroxyphenyl)hydracrylic acid
3-Hydroxy-3-(3'-hydroxyphenyl)propionic acid
beta, m-Dihydroxyphenylpropionic acid
beta, meta-Dihydroxyphenylpropionic acid
m-Hydroxyphenylhydracrylic acid
Chemical FormulaC9H10O4
Average Mass182.1733 Da
Monoisotopic Mass182.05791 Da
IUPAC Name3-hydroxy-3-(3-hydroxyphenyl)propanoic acid
Traditional Namemhpha
CAS Registry Number3247-75-4
SMILES
OC(CC(O)=O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C9H10O4/c10-7-3-1-2-6(4-7)8(11)5-9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
InChI KeyKHTAGVZHYUZYMF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-08-23View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-15View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-15View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK 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-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Beta-hydroxy acid
  • Phenol
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Benzenoid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.31 g/LALOGPS
logP0.68ALOGPS
logP0.68ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.31 m³·mol⁻¹ChemAxon
Polarizability17.31 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002643
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029822
KNApSAcK IDC00052316
Chemspider ID93013
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6729
PubChem Compound102959
PDB IDNot Available
ChEBI ID86369
Good Scents IDNot Available
References
General References
  1. Shaw W: Increased urinary excretion of a 3-(3-hydroxyphenyl)-3-hydroxypropionic acid (HPHPA), an abnormal phenylalanine metabolite of Clostridia spp. in the gastrointestinal tract, in urine samples from patients with autism and schizophrenia. Nutr Neurosci. 2010 Jun;13(3):135-43. doi: 10.1179/147683010X12611460763968. [PubMed:20423563 ]
  2. Kesli R, Gokcen C, Bulug U, Terzi Y: Investigation of the relation between anaerobic bacteria genus clostridium and late-onset autism etiology in children. J Immunoassay Immunochem. 2014;35(1):101-9. doi: 10.1080/15321819.2013.792834. [PubMed:24063620 ]
  3. Mussap M, Siracusano M, Noto A, Fattuoni C, Riccioni A, Rajula HSR, Fanos V, Curatolo P, Barberini L, Mazzone L: The Urine Metabolome of Young Autistic Children Correlates with Their Clinical Profile Severity. Metabolites. 2020 Nov 23;10(11). pii: metabo10110476. doi: 10.3390/metabo10110476. [PubMed:33238400 ]
  4. Noto A, Fanos V, Barberini L, Grapov D, Fattuoni C, Zaffanello M, Casanova A, Fenu G, De Giacomo A, De Angelis M, Moretti C, Papoff P, Ditonno R, Francavilla R: The urinary metabolomics profile of an Italian autistic children population and their unaffected siblings. J Matern Fetal Neonatal Med. 2014 Oct;27 Suppl 2:46-52. doi: 10.3109/14767058.2014.954784. [PubMed:25284177 ]
  5. Obrenovich ME, Donskey CJ, Schiefer IT, Bongiovanni R, Li L, Jaskiw GE: Quantification of phenolic acid metabolites in humans by LC-MS: a structural and targeted metabolomics approach. Bioanalysis. 2018 Oct;10(19):1591-1608. doi: 10.4155/bio-2018-0140. [PubMed:30295550 ]