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Showing NP-Card for Hydantoin-5-propionic acid (NP0086729)

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Record Information
Version2.0
Created at2022-05-11 16:29:22 UTC
Updated at2022-05-11 16:29:22 UTC
NP-MRD IDNP0086729
Secondary Accession NumbersNone
Natural Product Identification
Common NameHydantoin-5-propionic acid
DescriptionHydantoin-5-propionic acid, also known as hydantoin-propionate, belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4. A imidazolidine-2,4-dione that is hydantoin substituted by a 2-carboxyethyl group at position 4. Hydantoin-5-propionic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Hydantoin-5-propionic acid was first documented in 1963 (PMID: 13960896). Hydantoin-5-propionic acid exists in all living organisms, ranging from bacteria to humans (PMID: 3760095) (PMID: 5835442).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086729 (Hydantoin-5-propionic acid)


  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 NP0086729 (Hydantoin-5-propionic acid)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
    2.6492    1.0122    1.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3044    0.5093    0.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.3043   -0.6092 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7499   -0.8397    0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4301   -1.0140   -0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7760   -0.4116    0.3805 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9106   -0.8433   -0.4856 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7467    0.2677   -0.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8599    0.2570   -1.3565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1299    1.4121   -0.1633 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8930    1.0339    0.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1035    1.8591    0.9457 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3485    1.3781   -1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5384   -1.4719   -0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042   -1.2783    1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218   -2.1395   -0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4951   -0.7348   -1.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333   -0.8882    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0676   -1.8004   -0.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4961    2.3881   -0.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  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  1
  7 19  1  0
 10 20  1  0
M  END
Download

3D SDF for NP0086729 (Hydantoin-5-propionic acid)


  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>
NP0086729

> <DATABASE_NAME>
NP-MRD

> <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 NP0086729 (Hydantoin-5-propionic acid)

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PDB for NP0086729 (Hydantoin-5-propionic acid)
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 NP0086729 (Hydantoin-5-propionic acid)
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SMILES for NP0086729 (Hydantoin-5-propionic acid)
OC(=O)CCC1NC(=O)NC1=O
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INCHI for NP0086729 (Hydantoin-5-propionic acid)
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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View in JSmol
Synonyms
ValueSource
Hydantoin-propionateKegg
Hydantoin-propionic acidGenerator
Hydantoin-5-propionateGenerator
1-(2,4-(3H,5H)Imidazoledione)propionic acidHMDB
Hydantoin-5-propionic acidGenerator
Chemical FormulaC6H8N2O4
Average Mass172.1387 Da
Monoisotopic Mass172.04841 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine  substituted by ketone group at positions 2 and 4.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassAzolidines  
Sub ClassImidazolidines  
Direct ParentHydantoins  
Alternative Parents
Substituents
  • Hydantoin
    • 

  • Alpha-amino acid or derivatives
    • 

  • 5-monosubstituted hydantoin
    • 

  • N-acyl urea
    • 

  • Ureide
    • 

  • Dicarboximide
    • 

  • Carbonic acid derivative
    • 

  • Urea
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Azacycle
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.4ALOGPS
logP-1.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.33 m³·mol⁻¹ChemAxon
Polarizability15.11 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001212  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022493  
KNApSAcK IDNot Available
Chemspider ID761  
KEGG Compound IDC05565  
BioCyc IDHYDANTOIN-5-PROPIONATE  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6084  
PubChem Compound782  
PDB IDNot Available
ChEBI ID28297  
Good Scents IDNot Available
References
General References
  1. Duran M, Bruinvis L, Wadman SK: Quantitative gas chromatographic determination of urinary hydantoin-5-propionic acid in patients with disorders of folate/vitamin B12 metabolism. J Chromatogr. 1986 Sep 5;381(2):401-5. doi: 10.1016/s0378-4347(00)83606-3. [PubMed:3760095  ] 
  2. HASSALL H, GREENBERG DM: The oxidation of 4(5)-imidazolone-5(4)-propionic acid to hydantoin-5-propionic acid by xanthine oxidase. Biochim Biophys Acta. 1963 Mar 12;67:507-10. doi: 10.1016/0006-3002(63)91857-2. [PubMed:13960896  ] 
  3. Middleton JE: Detection by paper chromatography of imidazoles, including hydantoin-5-propionic acid, in urine after histidine dosage. J Clin Pathol. 1965 Sep;18(5):605-10. doi: 10.1136/jcp.18.5.605. [PubMed:5835442  ]