Showing metabocard for Hydantoin-5-propionic acid (MMDBc0000565)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:40:39 UTC
Update Date2024-04-30 19:33:01 UTC
Metabolite IDMMDBc0000565
Metabolite Identification
Common NameHydantoin-5-propionic acid
DescriptionHydantoin-5-propionic acid is a metabolite of histidine, urinary hydantoin-5-propionic acid occur in patients with disorders of folate/ vitamin B12 metabolism (PMID: 3760095 ). Folic acid non-dependent excessive formiminoglutamic aciduria (Figlu-uria) is an extremely rare disorder; treatment with oral folate supplements (15 mg/day) for 3 weeks failed to reduce urinary hydantoin-5-propionic acid (PMID: 8487495 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9253285c98>


  Mrv0541 02231218592D          

 12 12  0  0  0  0            999 V2000
    9.0084  -16.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0084  -17.7085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7930  -17.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2779  -17.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7930  -16.6285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3409  -16.3986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0479  -18.7480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1029  -17.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5154  -18.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3404  -18.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7529  -18.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7529  -17.2960    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  1  1  0  0  0  0
  1  6  2  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f9253285c98>

HMDB0001212
     RDKit          3D
Hydantoin-5-propionic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.3692   -1.1130    0.5076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768    0.1474    0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4333    0.7649    1.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3396    0.9468   -0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2956    0.0951   -0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -0.7749    0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1836    0.0130    1.0565 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3899    0.4351    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1099    1.4152    0.7626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6472   -0.4358   -0.6830 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5969   -1.3740   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6103   -2.4918   -1.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3573    0.6566    0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8704    1.4890   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9137    1.7215    0.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683   -0.5341   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365    0.7808   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0900   -1.5933    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991    0.2376    2.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4633   -0.3862   -1.3526 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11  6  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
 10 20  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9253285c98>


  Mrv0541 02231218592D          

 12 12  0  0  0  0            999 V2000
    9.0084  -16.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0084  -17.7085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7930  -17.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2779  -17.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7930  -16.6285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3409  -16.3986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0479  -18.7480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1029  -17.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5154  -18.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3404  -18.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7529  -18.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7529  -17.2960    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  1  1  0  0  0  0
  1  6  2  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000565

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CCC1NC(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8N2O4/c9-4(10)2-1-3-5(11)8-6(12)7-3/h3H,1-2H2,(H,9,10)(H2,7,8,11,12)

> <INCHI_KEY>
VWFWNXQAMGDPGG-UHFFFAOYSA-N

> <FORMULA>
C6H8N2O4

> <MOLECULAR_WEIGHT>
172.1387

> <EXACT_MASS>
172.048406754

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
15.111565751961795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2,5-dioxoimidazolidin-4-yl)propanoic acid

> <ALOGPS_LOGP>
-1.44

> <JCHEM_LOGP>
-1.2346069303333334

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.378523545784746

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9202957105549956

> <JCHEM_PKA_STRONGEST_BASIC>
-8.235701429485367

> <JCHEM_POLAR_SURFACE_AREA>
95.5

> <JCHEM_REFRACTIVITY>
36.330400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydantoin-5-propionic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f9253285c98>

HMDB0001212
     RDKit          3D
Hydantoin-5-propionic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.3692   -1.1130    0.5076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768    0.1474    0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4333    0.7649    1.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3396    0.9468   -0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2956    0.0951   -0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -0.7749    0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1836    0.0130    1.0565 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3899    0.4351    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1099    1.4152    0.7626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6472   -0.4358   -0.6830 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5969   -1.3740   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6103   -2.4918   -1.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3573    0.6566    0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8704    1.4890   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9137    1.7215    0.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683   -0.5341   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365    0.7808   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0900   -1.5933    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991    0.2376    2.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4633   -0.3862   -1.3526 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11  6  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
 10 20  1  0
M  END
Download

PDB for #<Metabolite:0x00007f9253285c98>

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  C   UNK     0      16.816 -31.516   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      16.816 -33.056   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      18.280 -33.532   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.185 -32.286   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      18.280 -31.040   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      15.570 -30.611   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      18.756 -34.996   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      20.725 -32.286   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.495 -33.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.035 -33.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      23.805 -34.953   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      23.805 -32.286   0.000  0.00  0.00           O+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    1                                                       
CONECT    6    1                                                            
CONECT    7    3                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   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 #<Metabolite:0x00007f9253285c98>

COMPND    HMDB0001212
HETATM    1  O1  UNL     1      -2.369  -1.113   0.508  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.377   0.147   0.460  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.433   0.765   1.124  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.340   0.947  -0.250  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.296   0.095  -0.888  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.478  -0.775   0.052  1.00  0.00           C  
HETATM    7  N1  UNL     1       1.184   0.013   1.056  1.00  0.00           N  
HETATM    8  C5  UNL     1       2.390   0.435   0.416  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.110   1.415   0.763  1.00  0.00           O  
HETATM   10  N2  UNL     1       2.647  -0.436  -0.683  1.00  0.00           N  
HETATM   11  C6  UNL     1       1.597  -1.374  -0.697  1.00  0.00           C  
HETATM   12  O4  UNL     1       1.610  -2.492  -1.236  1.00  0.00           O  
HETATM   13  H1  UNL     1      -4.357   0.657   0.688  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.870   1.489  -1.061  1.00  0.00           H  
HETATM   15  H3  UNL     1      -0.914   1.721   0.424  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.768  -0.534  -1.657  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.436   0.781  -1.377  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.090  -1.593   0.507  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.899   0.238   2.034  1.00  0.00           H  
HETATM   20  H8  UNL     1       3.463  -0.386  -1.353  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   11   18
CONECT    7    8   19
CONECT    8    9    9   10
CONECT   10   11   20
CONECT   11   12   12
END
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SMILES for #<Metabolite:0x00007f9253285c98>

OC(=O)CCC1NC(=O)NC1=O
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INCHI for #<Metabolite:0x00007f9253285c98>

InChI=1S/C6H8N2O4/c9-4(10)2-1-3-5(11)8-6(12)7-3/h3H,1-2H2,(H,9,10)(H2,7,8,11,12)
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Synonyms
ValueSource
Hydantoin-propionateKegg
Hydantoin-propionic acidGenerator
Hydantoin-5-propionateGenerator
1-(2,4-(3H,5H)Imidazoledione)propionic acidMeSH
Hydantoin-5-propionic acidGenerator
Molecular FormulaC6H8N2O4
Average Mass172.1387
Monoisotopic Mass172.048406754
IUPAC Name3-(2,5-dioxoimidazolidin-4-yl)propanoic acid
Traditional Namehydantoin-5-propionic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCC1NC(=O)NC1=O
InChI Identifier
InChI=1S/C6H8N2O4/c9-4(10)2-1-3-5(11)8-6(12)7-3/h3H,1-2H2,(H,9,10)(H2,7,8,11,12)
InChI KeyVWFWNXQAMGDPGG-UHFFFAOYSA-N