Showing metabocard for Desaminotyrosine (MMDBc0000409)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:37:06 UTC
Update Date2024-04-30 19:32:16 UTC
Metabolite IDMMDBc0000409
Metabolite Identification
Common NameDesaminotyrosine
DescriptionDesaminotyrosine, also known as 4-hydroxyphenylpropionic acid, is a normal constituent of human urine. It is a product of tyrosine metabolism; its concentration in urine increases in patients with gastrointestinal diseases. Desaminotyrosine is a major phenolic acid breakdown product of proanthocyanidin metabolism (PMID:15315398 ). Urinary desaminotyrosine is produced by Clostridium sporogenes and C. botulinum (PMID:29168502 ). Desaminotyrosine is also found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas, and Staphylococcus (PMID:29168502 , 28393285 , 19961416 ). Desaminotyrosine is a phenolic acid metabolite formed by the gut microflora detected after the consumption of whole grain.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fa50a7f2338>


  Mrv1652309272007442D          

 12 12  0  0  0  0            999 V2000
 9994.8588 9994.9198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7181 9996.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4320 9996.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1481 9996.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8621 9996.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1481 9997.3955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0038 9996.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2895 9996.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5748 9996.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5748 9995.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2893 9994.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0038 9995.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
  1 10  1  0  0  0  0
  7  2  1  0  0  0  0
  2  3  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fa50a7f2338>

HMDB0002199
     RDKit          3D
Desaminotyrosine
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.9245   -1.1465    0.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4159   -0.1462    0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1554    0.9986   -0.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190   -0.1791   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    0.0213    0.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2698    0.0033    0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9062    1.1783    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2330    1.1387   -0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9316   -0.0290   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2666   -0.0267   -0.5377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3188   -1.2122    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9861   -1.1880    0.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1352    1.8087    0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7944    0.6581   -1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7410   -1.1612   -0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848    1.0036    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4078   -0.7802    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3141    2.0900    0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7441    2.0488   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632   -0.8363   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8942   -2.1198    0.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4999   -2.1241    0.7325 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  7 18  1  0
  8 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fa50a7f2338>


  Mrv1652309272007442D          

 12 12  0  0  0  0            999 V2000
 9994.8588 9994.9198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7181 9996.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4320 9996.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1481 9996.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8621 9996.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1481 9997.3955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0038 9996.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2895 9996.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5748 9996.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5748 9995.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2893 9994.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0038 9995.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
  1 10  1  0  0  0  0
  7  2  1  0  0  0  0
  2  3  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000409

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CCC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)

> <INCHI_KEY>
NMHMNPHRMNGLLB-UHFFFAOYSA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.1739

> <EXACT_MASS>
166.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.971746796751624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
1.7519974486666663

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.50593673911279

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.214213970870649

> <JCHEM_PKA_STRONGEST_BASIC>
-5.958297991799353

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
43.947500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyphenyl propionic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fa50a7f2338>

HMDB0002199
     RDKit          3D
Desaminotyrosine
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.9245   -1.1465    0.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4159   -0.1462    0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1554    0.9986   -0.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190   -0.1791   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    0.0213    0.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2698    0.0033    0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9062    1.1783    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2330    1.1387   -0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9316   -0.0290   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2666   -0.0267   -0.5377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3188   -1.2122    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9861   -1.1880    0.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1352    1.8087    0.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7944    0.6581   -1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7410   -1.1612   -0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848    1.0036    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4078   -0.7802    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3141    2.0900    0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7441    2.0488   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632   -0.8363   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8942   -2.1198    0.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4999   -2.1241    0.7325 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  7 18  1  0
  8 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

PDB for #<Metabolite:0x00007fa50a7f2338>

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8657.0708657.184   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8662.4078660.264   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8663.7408659.494   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.0768660.264   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8666.4098659.494   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8665.0768661.805   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8661.0748659.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.7408660.263   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8658.4068659.493   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8658.4068657.953   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8659.7408657.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.0748657.953   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    7    3                                                       
CONECT    3    4    2                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    8   12    2                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    1                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for #<Metabolite:0x00007fa50a7f2338>

COMPND    HMDB0002199
HETATM    1  O1  UNL     1       3.924  -1.147   0.575  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.416  -0.146   0.043  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.155   0.999  -0.117  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.019  -0.179  -0.420  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.150   0.021   0.829  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.270   0.003   0.471  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.906   1.178   0.133  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.233   1.139  -0.198  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.932  -0.029  -0.199  1.00  0.00           C  
HETATM   10  O3  UNL     1      -4.267  -0.027  -0.538  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.319  -1.212   0.135  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.986  -1.188   0.469  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.135   1.809   0.488  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.794   0.658  -1.117  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.741  -1.161  -0.853  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.485   1.004   1.250  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.408  -0.780   1.548  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.314   2.090   0.145  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.744   2.049  -0.465  1.00  0.00           H  
HETATM   20  H8  UNL     1      -4.863  -0.836  -0.567  1.00  0.00           H  
HETATM   21  H9  UNL     1      -2.894  -2.120   0.124  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.500  -2.124   0.732  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7    7   12
CONECT    7    8   18
CONECT    8    9    9   19
CONECT    9   10   11
CONECT   10   20
CONECT   11   12   12   21
CONECT   12   22
END
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SMILES for #<Metabolite:0x00007fa50a7f2338>

OC(=O)CCC1=CC=C(O)C=C1
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INCHI for #<Metabolite:0x00007fa50a7f2338>

InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)
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Synonyms
ValueSource
3-(p-Hydroxyphenyl)propionic acidChEBI
4-Hydroxyphenylpropionic acidChEBI
beta-(p-Hydroxyphenyl)propionic acidChEBI
Dihydro-p-coumaric acidChEBI
HYDROXYPHENYL propionIC ACIDChEBI
p-Hydroxyhydrocinnamic acidChEBI
p-Hydroxyphenylpropionic acidChEBI
Phloretinic acidChEBI
3-(4-Hydroxyphenyl)propanoateKegg
3-(4-Hydroxyphenyl)propionateGenerator
3-(p-Hydroxyphenyl)propionateGenerator
4-HydroxyphenylpropionateGenerator
b-(p-Hydroxyphenyl)propionateGenerator
b-(p-Hydroxyphenyl)propionic acidGenerator
beta-(p-Hydroxyphenyl)propionateGenerator
Β-(p-hydroxyphenyl)propionateGenerator
Β-(p-hydroxyphenyl)propionic acidGenerator
Dihydro-p-coumarateGenerator
HYDROXYPHENYL propionateGenerator
p-HydroxyhydrocinnamateGenerator
p-HydroxyphenylpropionateGenerator
PhloretinateGenerator
PhloretateGenerator
3-(4-Hydroxyphenyl)propanoic acidGenerator
3-(4'-Hydroxyphenyl)-propionateHMDB
3-(4'-Hydroxyphenyl)-propionic acidHMDB
3-(4'-Hydroxyphenyl)propionic acidHMDB
3-(4-Hydroxy-phenyl)-propionateHMDB
3-(4-Hydroxy-phenyl)-propionic acidHMDB
3-(4-Hydroxyphenyl)-propionateHMDB
3-(4-Hydroxyphenyl)-propionic acidHMDB
3-(Para-hydroxyphenyl)propionateHMDB
3-(Para-hydroxyphenyl)propionic acidHMDB
4'-Hydroxyphenylpropionic acidHMDB
4-(4-HydroxyphenylpropanoateHMDB
4-(4-Hydroxyphenylpropanoic acidHMDB
4-Hydroxy-(9ci)benzenepropanoateHMDB
4-Hydroxy-(9ci)benzenepropanoic acidHMDB
4-Hydroxy-benzenepropanoateHMDB
4-Hydroxy-benzenepropanoic acidHMDB
4-HydroxybenzenepropanoateHMDB
4-Hydroxybenzenepropanoic acidHMDB
hydro-P-CoumarateHMDB
Hydro-p-coumaric acidHMDB
Hydroxy-hydrocinnamic acidHMDB
N-Hydroxysuccinimide esterHMDB
P-Hydroxy-benzene propionateHMDB
P-Hydroxy-benzene propionic acidHMDB
P-Hydroxy-hydrocinnamateHMDB
P-Hydroxy-hydrocinnamic acidHMDB
4-Hydroxyhydrocinnamic acidMeSH, HMDB
DesaminotyrosineChEBI
3-(4'-Hydroxyphenyl)propanoic acidPhytoBank
4-Hydroxybenzenepropionic acidPhytoBank
2,3-Dihydro-p-coumaric acidPhytoBank
3-(4’-Hydroxyphenyl)propanoic acidPhytoBank
3-(4’-Hydroxyphenyl)propionic acidPhytoBank
3-(p-Hydroxyphenyl)propanoic acidPhytoBank
4-(2-Carboxyethyl)phenolPhytoBank
4-(2-Carboxylethyl)phenolPhytoBank
4-Hydroxydihydrocinnamic acidPhytoBank
Dihydrocoumaric acidPhytoBank
p-Hydroxybenzene propanoic acidPhytoBank
p-Hydroxybenzene propionic acidPhytoBank
p-Hydroxyphenylpropanoic acidPhytoBank
beta-(4-Hydroxyphenyl)propanoic acidPhytoBank
beta-(4-Hydroxyphenyl)propionic acidPhytoBank
β-(4-Hydroxyphenyl)propanoic acidPhytoBank
β-(4-Hydroxyphenyl)propionic acidPhytoBank
beta-(p-Hydroxyphenyl)propanoic acidPhytoBank
β-(p-Hydroxyphenyl)propanoic acidPhytoBank
Molecular FormulaC9H10O3
Average Mass166.1739
Monoisotopic Mass166.062994186
IUPAC Name3-(4-hydroxyphenyl)propanoic acid
Traditional Namehydroxyphenyl propionic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)
InChI KeyNMHMNPHRMNGLLB-UHFFFAOYSA-N