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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:51:04 UTC

Update Date

2021-09-26 22:56:09 UTC

HMDB ID

HMDB0246838

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-Phenylhydantoin

Description

5-Phenylhydantoin belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. 5-Phenylhydantoin exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on 5-Phenylhydantoin. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-phenylhydantoin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-Phenylhydantoin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.334  11.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  10.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  10.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   8.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   8.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   8.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   6.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.580   5.565   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564   4.100   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.088   5.565   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.104   4.100   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       4.044   6.041   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.342   2.854   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5    7                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7   11   12                                                  
CONECT    9   10   11   13                                                  
CONECT   10    7    9                                                       
CONECT   11    8    9                                                       
CONECT   12    8                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Phenylhydantoin sodium	HMDB
5-Phenylhydantoin, (+-)-isomer	HMDB
5-Phenylhydantoin, (R)-isomer	HMDB
5-Phenylhydantoin, (S)-isomer	HMDB
5-Phenylhydantoin	MeSH

Chemical Formula

C₉H₈N₂O₂

Average Molecular Weight

176.172

Monoisotopic Molecular Weight

176.05857751

IUPAC Name

4-phenyl-4H-imidazole-2,5-diol

Traditional Name

5-phenyl-5H-imidazole-2,4-diol

CAS Registry Number

Not Available

SMILES

OC1=NC(C(O)=N1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C9H8N2O2/c12-8-7(10-9(13)11-8)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12,13)

InChI Key

NXQJDVBMMRCKQG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Phenylhydantoins

Alternative Parents

Substituents

5-phenylhydantoin
Phenylimidazolidine
Alpha-amino acid or derivatives
5-monosubstituted hydantoin
N-acyl urea
Ureide
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (PHENYLHYDANTOIN )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.62	ALOGPS
logP	1.74	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	4.52	ChemAxon
pKa (Strongest Basic)	0.033	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.18 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	46.45 m³·mol⁻¹	ChemAxon
Polarizability	17.17 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	138.579	30932474
DeepCCS	[M-H]-	136.183	30932474
DeepCCS	[M-2H]-	171.256	30932474
DeepCCS	[M+Na]+	145.715	30932474
AllCCS	[M+H]+	140.4	32859911
AllCCS	[M+H-H2O]+	136.1	32859911
AllCCS	[M+NH4]+	144.4	32859911
AllCCS	[M+Na]+	145.6	32859911
AllCCS	[M-H]-	136.9	32859911
AllCCS	[M+Na-2H]-	137.4	32859911
AllCCS	[M+HCOO]-	138.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.8864 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.8 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1260.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	320.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	112.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	196.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	326.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	445.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	778.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	284.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	918.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	362.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	200.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	91.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Phenylhydantoin	OC1=NC(C(O)=N1)C1=CC=CC=C1	3130.8	Standard polar	33892256
5-Phenylhydantoin	OC1=NC(C(O)=N1)C1=CC=CC=C1	1852.1	Standard non polar	33892256
5-Phenylhydantoin	OC1=NC(C(O)=N1)C1=CC=CC=C1	1863.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Phenylhydantoin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2900000000-29031da4f3df492b09a7	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Phenylhydantoin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Phenylhydantoin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Phenylhydantoin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Phenylhydantoin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Phenylhydantoin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Phenylhydantoin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Phenylhydantoin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Phenylhydantoin 10V, Positive-QTOF	splash10-004i-0900000000-b8ee69b6ad9468557700	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Phenylhydantoin 20V, Positive-QTOF	splash10-0zi0-0900000000-2608f617a5a27f1e6151	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Phenylhydantoin 40V, Positive-QTOF	splash10-0zfr-6900000000-0c826d2a1ec8a246a52d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Phenylhydantoin 10V, Negative-QTOF	splash10-004i-2900000000-2fd3b420a7b79ffe7263	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Phenylhydantoin 20V, Negative-QTOF	splash10-002f-9700000000-5ba49553bdd1e846ac2d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Phenylhydantoin 40V, Negative-QTOF	splash10-0f6x-9500000000-396218cd005d46fe3c61	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Phenylhydantoin 10V, Positive-QTOF	splash10-004i-0900000000-72b2beb77ff784d05490	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Phenylhydantoin 20V, Positive-QTOF	splash10-0ugi-2900000000-0c30a9d25db568f80182	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Phenylhydantoin 40V, Positive-QTOF	splash10-0udi-4900000000-accbe98700d8ea46df6e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Phenylhydantoin 10V, Negative-QTOF	splash10-0a4i-0900000000-ca891ec865f0b18f774e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Phenylhydantoin 20V, Negative-QTOF	splash10-054o-9700000000-2b7dcd52fe2a35e704b3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Phenylhydantoin 40V, Negative-QTOF	splash10-0006-9300000000-2eec2b1f43ac2ef28d16	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

977

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1002

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 5-Phenylhydantoin (HMDB0246838)

MOL for HMDB0246838 (5-Phenylhydantoin)

3D MOL for HMDB0246838 (5-Phenylhydantoin)

3D SDF for HMDB0246838 (5-Phenylhydantoin)

3D-SDF for HMDB0246838 (5-Phenylhydantoin)

PDB for HMDB0246838 (5-Phenylhydantoin)

3D PDB for HMDB0246838 (5-Phenylhydantoin)

SMILES for HMDB0246838 (5-Phenylhydantoin)

INCHI for HMDB0246838 (5-Phenylhydantoin)

Structure for HMDB0246838 (5-Phenylhydantoin)

3D Structure for HMDB0246838 (5-Phenylhydantoin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra