Showing metabocard for 1-Pyrroline-4-hydroxy-2-carboxylate (MMDBc0049981)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 22:47:33 UTC
Update Date2024-04-30 20:42:22 UTC
Metabolite IDMMDBc0049981
Metabolite Identification
Common Name1-Pyrroline-4-hydroxy-2-carboxylate
DescriptionMuch or all of the pyrrole-2-carboxylate (PCA) in human urine may be formed in urine from a labile precursor, presumably delta(1)-pyrroline-4-hydroxy-2-carboxylate. Normal human values for endogenous urinary PCA in 16 individuals averaged 0.51 mumol/day, with a range of 0.20-1.3 mumol and a SD of 0.31 mumol. The probable source of human PCA is free hydroxy-L-proline, as inferred from the high value for PCA in the urine of a subject with hereditary hydroxyprolinemia, and from the threeto eightfold elevation in PCA excretion by two normal subjects after a large oral load of hydroxyl-L-proline. (PMID: 4430715 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005634c2c9c9b0>


  Mrv0541 02231219262D          

  9  9  0  0  0  0            999 V2000
   27.3783   -6.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8573   -3.6038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4157   -4.9628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4808   -4.1808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8933   -5.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1483   -4.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0683   -5.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0288   -4.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8134   -4.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  4  6  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00005634c2c9c9b0>

HMDB0002234
     RDKit          3D
1-Pyrroline-4-hydroxy-2-carboxylate
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.6149   -1.5716    0.4419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3188   -0.3859    0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3112    0.5559    0.0835 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9394    0.0230    0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4788    1.2110   -0.0897 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9479    1.2571   -0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4016   -0.1737   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4988   -0.4926    0.4807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116   -0.9183    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3254    1.1543   -0.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3880    1.6052    0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3348    1.8640   -0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5655   -0.4309   -1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2840   -0.7320   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288   -1.8857   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3277   -1.0797    1.3785 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9  4  1  0
  3 10  1  0
  6 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
  9 15  1  0
  9 16  1  0
M  END
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3D SDF for #<Metabolite:0x00005634c2c9c9b0>


  Mrv0541 02231219262D          

  9  9  0  0  0  0            999 V2000
   27.3783   -6.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8573   -3.6038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4157   -4.9628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4808   -4.1808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8933   -5.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1483   -4.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0683   -5.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0288   -4.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8134   -4.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  4  6  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049981

> <DATABASE_NAME>
MIME

> <SMILES>
OC1CN=C(C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h3,7H,1-2H2,(H,8,9)

> <INCHI_KEY>
AOMLMYXPXUTBQH-UHFFFAOYSA-N

> <FORMULA>
C5H7NO3

> <MOLECULAR_WEIGHT>
129.114

> <EXACT_MASS>
129.042593095

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
11.755079755935292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-3,4-dihydro-2H-pyrrole-5-carboxylic acid

> <ALOGPS_LOGP>
-0.87

> <JCHEM_LOGP>
-0.3897816506666668

> <ALOGPS_LOGS>
-0.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.509629903901676

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6562839469062225

> <JCHEM_PKA_STRONGEST_BASIC>
0.5298136816870899

> <JCHEM_POLAR_SURFACE_AREA>
69.89

> <JCHEM_REFRACTIVITY>
29.046299999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.83e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-4,5-dihydro-3H-pyrrole-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00005634c2c9c9b0>

HMDB0002234
     RDKit          3D
1-Pyrroline-4-hydroxy-2-carboxylate
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.6149   -1.5716    0.4419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3188   -0.3859    0.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3112    0.5559    0.0835 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9394    0.0230    0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4788    1.2110   -0.0897 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9479    1.2571   -0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4016   -0.1737   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4988   -0.4926    0.4807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116   -0.9183    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3254    1.1543   -0.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3880    1.6052    0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3348    1.8640   -0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5655   -0.4309   -1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2840   -0.7320   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288   -1.8857   -0.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3277   -1.0797    1.3785 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9  4  1  0
  3 10  1  0
  6 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
  9 15  1  0
  9 16  1  0
M  END
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PDB for #<Metabolite:0x00005634c2c9c9b0>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      51.106 -11.420   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      46.400  -6.727   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      45.576  -9.264   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      49.431  -7.804   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      50.201 -10.174   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      50.677  -8.709   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      48.661 -10.174   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      46.720  -8.233   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.185  -8.709   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    8                                                            
CONECT    3    8                                                            
CONECT    4    6    9                                                       
CONECT    5    1    6    7                                                  
CONECT    6    4    5                                                       
CONECT    7    5    9                                                       
CONECT    8    2    3    9                                                  
CONECT    9    4    7    8                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for #<Metabolite:0x00005634c2c9c9b0>

COMPND    HMDB0002234
HETATM    1  O1  UNL     1       2.615  -1.572   0.442  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.319  -0.386   0.228  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.311   0.556   0.084  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.939   0.023   0.128  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.479   1.211  -0.090  1.00  0.00           N  
HETATM    6  C3  UNL     1      -0.948   1.257  -0.127  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.402  -0.174  -0.300  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.499  -0.493   0.481  1.00  0.00           O  
HETATM    9  C5  UNL     1      -0.212  -0.918   0.269  1.00  0.00           C  
HETATM   10  H1  UNL     1       3.325   1.154  -0.720  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.388   1.605   0.848  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.335   1.864  -0.964  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.565  -0.431  -1.358  1.00  0.00           H  
HETATM   14  H5  UNL     1      -3.284  -0.732  -0.066  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.029  -1.886  -0.233  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.328  -1.080   1.378  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5    5    9
CONECT    5    6
CONECT    6    7   11   12
CONECT    7    8    9   13
CONECT    8   14
CONECT    9   15   16
END
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SMILES for #<Metabolite:0x00005634c2c9c9b0>

OC1CN=C(C1)C(O)=O
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INCHI for #<Metabolite:0x00005634c2c9c9b0>

InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h3,7H,1-2H2,(H,8,9)
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Synonyms
ValueSource
1-Pyrroline-4-hydroxy-2-carboxylic acidGenerator
4-Hydroxy-1-pyrroline-2-carboxylateHMDB
4-Hydroxy-1-pyrroline-2-carboxylic acidHMDB
Molecular FormulaC5H7NO3
Average Mass129.114
Monoisotopic Mass129.042593095
IUPAC Name3-hydroxy-3,4-dihydro-2H-pyrrole-5-carboxylic acid
Traditional Name4-hydroxy-4,5-dihydro-3H-pyrrole-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC1CN=C(C1)C(O)=O
InChI Identifier
InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h3,7H,1-2H2,(H,8,9)
InChI KeyAOMLMYXPXUTBQH-UHFFFAOYSA-N