Showing metabocard for cis-4-hydroxy-L-proline (MMDBc0054396)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 23:10:31 UTC
Update Date2022-09-01 02:28:54 UTC
Metabolite IDMMDBc0054396
Metabolite Identification
Common Namecis-4-hydroxy-L-proline
Descriptioncis 4-Hydroxyproline, also known as L-allo-hydroxyproline, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. cis 4-Hydroxyproline is found, on average, in the highest concentration within a few different foods, such as oats (Avena sativa), ryes (Secale cereale), and wheats (Triticum) and in a lower concentration in white cabbages (Brassica oleracea L. var. capitata L. f. alba DC.), red bell peppers (Capsicum annuum), and garden onions (Allium cepa). cis 4-Hydroxyproline has also been detected, but not quantified in, green bell peppers (Capsicum annuum). This could make cis 4-hydroxyproline a potential biomarker for the consumption of these foods. cis 4-Hydroxyproline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on cis 4-Hydroxyproline.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f91f733bf90>


  Mrv1652304171922392D          

 11 11  0  0  1  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057   -0.8903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  4  5  1  1  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  3  7  1  1  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
  3 10  1  6  0  0  0
  4 11  1  6  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f91f733bf90>

HMDB0240251
     RDKit          3D
cis-4-Hydroxyproline
 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.6444    1.3053    0.4250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1939    0.2537   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0489   -0.8022   -0.2848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7950    0.1544   -0.4102 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0182   -0.8456    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770   -0.5462   -0.1080 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3543   -0.9171    0.7884 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    0.9517   -0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0451    1.3581   -0.1171 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2265   -1.4551    0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5880   -0.0964   -1.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3262   -1.8743    0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0888   -0.5952    1.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4510   -1.0894   -1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2203   -0.6023    0.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9906    1.4808    0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6372    1.1822   -1.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3673    2.1376   -0.6946 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  1  0
  6  8  1  0
  8  9  1  0
  9  4  1  0
  3 10  1  0
  4 11  1  6
  5 12  1  0
  5 13  1  0
  6 14  1  6
  7 15  1  0
  8 16  1  0
  8 17  1  0
  9 18  1  0
M  END
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3D SDF for #<Metabolite:0x00007f91f733bf90>


  Mrv1652304171922392D          

 11 11  0  0  1  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057   -0.8903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  4  5  1  1  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  3  7  1  1  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
  3 10  1  6  0  0  0
  4 11  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054396

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(O)CN[C@@]([H])(C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1

> <INCHI_KEY>
PMMYEEVYMWASQN-IMJSIDKUSA-N

> <FORMULA>
C5H9NO3

> <MOLECULAR_WEIGHT>
131.1299

> <EXACT_MASS>
131.058243159

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.22031859891446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-3.31

> <JCHEM_LOGP>
-3.7163188466782064

> <ALOGPS_LOGS>
0.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.856641323999913

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.641381950764853

> <JCHEM_PKA_STRONGEST_BASIC>
10.617096890348787

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
29.3822

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.92e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-hydroxyproline

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f91f733bf90>

HMDB0240251
     RDKit          3D
cis-4-Hydroxyproline
 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.6444    1.3053    0.4250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1939    0.2537   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0489   -0.8022   -0.2848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7950    0.1544   -0.4102 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0182   -0.8456    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770   -0.5462   -0.1080 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3543   -0.9171    0.7884 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    0.9517   -0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0451    1.3581   -0.1171 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2265   -1.4551    0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5880   -0.0964   -1.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3262   -1.8743    0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0888   -0.5952    1.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4510   -1.0894   -1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2203   -0.6023    0.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9906    1.4808    0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6372    1.1822   -1.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3673    2.1376   -0.6946 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  1  0
  6  8  1  0
  8  9  1  0
  9  4  1  0
  3 10  1  0
  4 11  1  6
  5 12  1  0
  5 13  1  0
  6 14  1  6
  7 15  1  0
  8 16  1  0
  8 17  1  0
  9 18  1  0
M  END
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PDB for #<Metabolite:0x00007f91f733bf90>

HEADER    PROTEIN                                 17-APR-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-19         0                                  
HETATM    1  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.290  -0.290   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.267  -1.375   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.109  -2.943   0.000  0.00  0.00           O+0
HETATM   10  H   UNK     0      -0.312   2.779   0.000  0.00  0.00           H+0
HETATM   11  H   UNK     0       1.131  -1.662   0.000  0.00  0.00           H+0
CONECT    1    3    4                                                       
CONECT    2    3    6                                                       
CONECT    3    1    2    7   10                                             
CONECT    4    1    5    6   11                                             
CONECT    5    4    8    9                                                  
CONECT    6    2    4                                                       
CONECT    7    3                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    3                                                            
CONECT   11    4                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x00007f91f733bf90>

COMPND    HMDB0240251
HETATM    1  O1  UNL     1      -2.644   1.305   0.425  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.194   0.254  -0.070  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.049  -0.802  -0.285  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.795   0.154  -0.410  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.018  -0.846   0.438  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.377  -0.546  -0.108  1.00  0.00           C  
HETATM    7  O3  UNL     1       2.354  -0.917   0.788  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.312   0.952  -0.333  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.045   1.358  -0.117  1.00  0.00           N  
HETATM   10  H1  UNL     1      -3.226  -1.455   0.473  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.588  -0.096  -1.472  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.326  -1.874   0.282  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.089  -0.595   1.510  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.451  -1.089  -1.089  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.220  -0.602   0.429  1.00  0.00           H  
HETATM   16  H7  UNL     1       1.991   1.481   0.390  1.00  0.00           H  
HETATM   17  H8  UNL     1       1.637   1.182  -1.354  1.00  0.00           H  
HETATM   18  H9  UNL     1      -0.367   2.138  -0.695  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5    9   11
CONECT    5    6   12   13
CONECT    6    7    8   14
CONECT    7   15
CONECT    8    9   16   17
CONECT    9   18
END
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SMILES for #<Metabolite:0x00007f91f733bf90>

[H][C@@]1(O)CN[C@@]([H])(C1)C(O)=O
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INCHI for #<Metabolite:0x00007f91f733bf90>

InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1
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Synonyms
ValueSource
(2S,4S)-4-Hydroxy-2-pyrrolidinecarboxylic acidChEBI
4-cis-L-HydroxyprolineChEBI
Allo-4-hydroxy-L-prolineChEBI
L-Allo-hydroxyprolineChEBI
L-cis-4-HydroxyprolineChEBI
L-AllohydroxyprolineKegg
(2S,4S)-4-Hydroxy-2-pyrrolidinecarboxylateGenerator
cis-4-Hydroxy-L-prolineHMDB
cis-HydroxyprolineHMDB
(4S)-4-Hydroxy-L-prolineHMDB
(2S,4S)-4-HydroxyprolineHMDB
(2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acidHMDB
(S)-allo-HydroxyprolineHMDB
4(S)-Hydroxy-2(S)-pyrrolidinecarboxylic acidHMDB
4-cis-Hydroxy-L-prolineHMDB
4-allo-HydroxyprolineHMDB
L-allo-4-HydroxyprolineHMDB
allo-4-HydroxyprolineHMDB
allo-Hydroxy-L-prolineHMDB
allo-L-HydroxyprolineHMDB
H-cis-Hyp-OHHMDB
NSC 206274HMDB
cis-4-HydroxyprolineHMDB, MeSH
HydroxyprolineMeSH, HMDB
4 HydroxyprolineMeSH, HMDB
4-HydroxyprolineMeSH, HMDB
OxyprolineMeSH, HMDB
cis 4 HydroxyprolineMeSH, HMDB
Molecular FormulaC5H9NO3
Average Mass131.1299
Monoisotopic Mass131.058243159
IUPAC Name(2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid
Traditional NameL-hydroxyproline
CAS Registry NumberNot Available
SMILES
[H][C@@]1(O)CN[C@@]([H])(C1)C(O)=O
InChI Identifier
InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1
InChI KeyPMMYEEVYMWASQN-IMJSIDKUSA-N