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

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:39 UTC

Update Date

2024-04-30 19:33:01 UTC

Metabolite ID

MMDBc0000565

Metabolite Identification

Common Name

Hydantoin-5-propionic acid

Description

Hydantoin-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

Synonyms

Value	Source
Hydantoin-propionate	Kegg
Hydantoin-propionic acid	Generator
Hydantoin-5-propionate	Generator
1-(2,4-(3H,5H)Imidazoledione)propionic acid	MeSH
Hydantoin-5-propionic acid	Generator

Molecular Formula

C₆H₈N₂O₄

Average Mass

172.1387

Monoisotopic Mass

172.048406754

IUPAC Name

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

Traditional Name

hydantoin-5-propionic acid

CAS Registry Number

Not 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 Key

VWFWNXQAMGDPGG-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Hydantoins

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:28297 )
imidazolidine-2,4-dione (CHEBI:28297 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.45 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-1.2	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	-8.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.5 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	36.33 m³·mol⁻¹	ChemAxon
Polarizability	15.11 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0a4i-3961000000-07de24d94e2304e2b597	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0059-3519000000-2edee3d23ebfb1aed306	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-3961000000-07de24d94e2304e2b597	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0059-3519000000-2edee3d23ebfb1aed306	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6t-9600000000-72cc8eb79a0737df29a0	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00ba-9720000000-c1c0fbcd1ed84d9507ac	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-19934f3de22343e3db0e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pc0-5900000000-c3114ac773b2d9b75270	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-46959f6a9b4087621187	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-4fb2343d2f66db0c6890	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ffx-4900000000-6c01203d4c8c99cf8f6c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d153c6a3d156a466ad59	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-5ee56d718be837eede1e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9300000000-4798e4cff31bc0a178e6	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-f929846fd3d130f328a3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-4e0de47e878bed79a35b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2900000000-4150d50600586f3cb148	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-18812b534520e1661316	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	2	Human ; Human supragingival plaque; Human subgingival plaque; Human feces; Human sputum; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0001212

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022493

KNApSAcK ID

Not Available

Chemspider ID

761

KEGG Compound ID

C05565

BioCyc ID

HYDANTOIN-5-PROPIONATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6084

PubChem Compound

782

PDB ID

Not Available

ChEBI ID

28297

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
Duran M, Dorland L, Meuleman EE, Renardel de Lavalette PA, Poll-The BT, Berger R: Formiminoglutamic/hydantoinpropionic aciduria in two siblings. J Inherit Metab Dis. 1993;16(1):155-6. doi: 10.1007/BF00711330. [PubMed:8487495 ]

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

MOL for #<Metabolite:0x00007fdb44c1ab70>

3D MOL for #<Metabolite:0x00007fdb44c1ab70>

3D SDF for #<Metabolite:0x00007fdb44c1ab70>

3D-SDF for #<Metabolite:0x00007fdb44c1ab70>

PDB for #<Metabolite:0x00007fdb44c1ab70>

3D PDB for #<Metabolite:0x00007fdb44c1ab70>

SMILES for #<Metabolite:0x00007fdb44c1ab70>

INCHI for #<Metabolite:0x00007fdb44c1ab70>

Structure for #<Metabolite:0x00007fdb44c1ab70>

3D Structure for #<Metabolite:0x00007fdb44c1ab70>