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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:23 UTC
Update Date2021-09-14 15:47:38 UTC
HMDB IDHMDB0013896
Secondary Accession Numbers
  • HMDB13896
Metabolite Identification
Common Name3'-HPPH
Description3'-HPPH, also called (5R)-5-(3-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione or 3’-hydroxyphenytoin, is a metabolite of Phenytoin. Phenytoin is an anticonvulsant used to treat epilepsy. 3'-HPPH belongs to the family of compounds known as Diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. 3'-HPPH or 3’-hydroxyphenytoin is only found in individuals that have used or taken Phenytoin.
Structure
Data?1582753152
SynonymsNot Available
Chemical FormulaC15H12N2O3
Average Molecular Weight268.2674
Monoisotopic Molecular Weight268.08479226
IUPAC Name(5R)-5-(3-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione
Traditional Name(5R)-5-(3-hydroxyphenyl)-5-phenylimidazolidine-2,4-dione
CAS Registry NumberNot Available
SMILES
OC1=CC(=CC=C1)[C@]1(NC(=O)NC1=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C15H12N2O3/c18-12-8-4-7-11(9-12)15(10-5-2-1-3-6-10)13(19)16-14(20)17-15/h1-9,18H,(H2,16,17,19,20)/t15-/m1/s1
InChI KeyFSPRLRPJSPWQNC-OAHLLOKOSA-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentPhenylhydantoins
Alternative Parents
Substituents
  • Diphenylmethane
  • 5-phenylhydantoin
  • Phenylimidazolidine
  • Alpha-amino acid or derivatives
  • 5-monosubstituted hydantoin
  • 1-hydroxy-2-unsubstituted benzenoid
  • N-acyl urea
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Ureide
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.67ALOGPS
logP1.84ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity72.16 m³·mol⁻¹ChemAxon
Polarizability26.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.86231661259
DarkChem[M-H]-160.15531661259
DeepCCS[M+H]+164.85930932474
DeepCCS[M-H]-162.50130932474
DeepCCS[M-2H]-195.79730932474
DeepCCS[M+Na]+171.02430932474
AllCCS[M+H]+161.032859911
AllCCS[M+H-H2O]+157.132859911
AllCCS[M+NH4]+164.632859911
AllCCS[M+Na]+165.632859911
AllCCS[M-H]-162.632859911
AllCCS[M+Na-2H]-162.032859911
AllCCS[M+HCOO]-161.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3'-HPPHOC1=CC(=CC=C1)[C@]1(NC(=O)NC1=O)C1=CC=CC=C13962.3Standard polar33892256
3'-HPPHOC1=CC(=CC=C1)[C@]1(NC(=O)NC1=O)C1=CC=CC=C12751.0Standard non polar33892256
3'-HPPHOC1=CC(=CC=C1)[C@]1(NC(=O)NC1=O)C1=CC=CC=C12733.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3'-HPPH,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)NC2=O)=C12742.6Semi standard non polar33892256
3'-HPPH,1TMS,isomer #2C[Si](C)(C)N1C(=O)NC(=O)[C@@]1(C1=CC=CC=C1)C1=CC=CC(O)=C12614.1Semi standard non polar33892256
3'-HPPH,1TMS,isomer #3C[Si](C)(C)N1C(=O)N[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O2584.9Semi standard non polar33892256
3'-HPPH,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)=C12636.8Semi standard non polar33892256
3'-HPPH,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)=C12580.8Standard non polar33892256
3'-HPPH,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)=C13697.6Standard polar33892256
3'-HPPH,2TMS,isomer #2C[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)=C12688.8Semi standard non polar33892256
3'-HPPH,2TMS,isomer #2C[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)=C12527.4Standard non polar33892256
3'-HPPH,2TMS,isomer #2C[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)=C13499.4Standard polar33892256
3'-HPPH,2TMS,isomer #3C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O2333.5Semi standard non polar33892256
3'-HPPH,2TMS,isomer #3C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O2543.1Standard non polar33892256
3'-HPPH,2TMS,isomer #3C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O3223.5Standard polar33892256
3'-HPPH,3TMS,isomer #1C[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=C12422.8Semi standard non polar33892256
3'-HPPH,3TMS,isomer #1C[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=C12536.5Standard non polar33892256
3'-HPPH,3TMS,isomer #1C[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)=C12993.1Standard polar33892256
3'-HPPH,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)NC2=O)=C13005.8Semi standard non polar33892256
3'-HPPH,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)[C@@]1(C1=CC=CC=C1)C1=CC=CC(O)=C12901.2Semi standard non polar33892256
3'-HPPH,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)N[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O2927.1Semi standard non polar33892256
3'-HPPH,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)=C13143.9Semi standard non polar33892256
3'-HPPH,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)=C12964.3Standard non polar33892256
3'-HPPH,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)=C13688.3Standard polar33892256
3'-HPPH,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)=C13205.7Semi standard non polar33892256
3'-HPPH,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)=C12955.6Standard non polar33892256
3'-HPPH,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)=C13596.9Standard polar33892256
3'-HPPH,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O2903.5Semi standard non polar33892256
3'-HPPH,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O2963.3Standard non polar33892256
3'-HPPH,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@](C2=CC=CC=C2)(C2=CC=CC(O)=C2)C1=O3276.2Standard polar33892256
3'-HPPH,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=C13154.7Semi standard non polar33892256
3'-HPPH,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=C13155.1Standard non polar33892256
3'-HPPH,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC([C@]2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)=C13160.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3'-HPPH GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fha-1910000000-07256907a664e226b29e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-HPPH GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2981000000-45e106686ee5bd86f8102017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-HPPH GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-HPPH GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-HPPH 10V, Positive-QTOFsplash10-014i-0290000000-84e48a5cbdf2651a23542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-HPPH 20V, Positive-QTOFsplash10-00kb-0960000000-c6b7c6e260986561fee22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-HPPH 40V, Positive-QTOFsplash10-0fdk-2900000000-9b697694cd4ed14b34022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-HPPH 10V, Negative-QTOFsplash10-014i-0090000000-985e5e440b324877f65b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-HPPH 20V, Negative-QTOFsplash10-014i-2190000000-94e8800e1b1868b448cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-HPPH 40V, Negative-QTOFsplash10-0006-8910000000-1f968e3f670dfcbab35f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-HPPH 10V, Negative-QTOFsplash10-014i-0090000000-bd7cd943428e7be367e72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-HPPH 20V, Negative-QTOFsplash10-00ke-5950000000-844d1044e0dfb175ac752021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-HPPH 40V, Negative-QTOFsplash10-0006-9500000000-3b3f6334c7bef7993d732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-HPPH 10V, Positive-QTOFsplash10-014i-0190000000-1b299a4a0e6a46c0bb5b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-HPPH 20V, Positive-QTOFsplash10-0002-0920000000-26fb64530d09354a7ea42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-HPPH 40V, Positive-QTOFsplash10-0fmj-5910000000-dcb3a5106906c7151aac2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID628070
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound719586
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available