Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:58:44 UTC
Update Date2021-09-14 15:02:27 UTC
HMDB IDHMDB0060776
Secondary Accession Numbers
  • HMDB60776
Metabolite Identification
Common Name5-Hydroxydantrolene
Description5-Hydroxydantrolene 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. 5-Hydroxydantrolene is a metabolite of dantrolene. 5-Hydroxydantrolene is an extremely weak basic (essentially neutral) compound (based on its pKa). Dantrolene sodium is a muscle relaxant that acts by abolishing excitation-contraction coupling in muscle cells, probably by action on the ryanodine receptor. It is the only specific and effective treatment for malignant hyperthermia, a rare, life-threatening disorder triggered by general anesthesia.
Structure
Data?1563866104
SynonymsNot Available
Chemical FormulaC14H10N4O6
Average Molecular Weight330.2524
Monoisotopic Molecular Weight330.060034072
IUPAC Name4,5-dihydroxy-1-[(E)-{[5-(4-nitrophenyl)furan-2-yl]methylidene}amino]-2,5-dihydro-1H-imidazol-2-one
Traditional Name4,5-dihydroxy-1-[(E)-{[5-(4-nitrophenyl)furan-2-yl]methylidene}amino]-5H-imidazol-2-one
CAS Registry NumberNot Available
SMILES
OC1N(\N=C\C2=CC=C(O2)C2=CC=C(C=C2)N(=O)=O)C(=O)N=C1O
InChI Identifier
InChI=1S/C14H10N4O6/c19-12-13(20)17(14(21)16-12)15-7-10-5-6-11(24-10)8-1-3-9(4-2-8)18(22)23/h1-7,13,20H,(H,16,19,21)/b15-7+
InChI KeyPGORTQZSSAZLCK-VIZOYTHASA-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentHydantoins
Alternative Parents
Substituents
  • Hydantoin
  • Alpha-amino acid or derivatives
  • Nitrobenzene
  • Nitroaromatic compound
  • Monocyclic benzene moiety
  • Semicarbazone
  • Benzenoid
  • Heteroaromatic compound
  • Dicarboximide
  • Furan
  • Semicarbazide
  • Organic nitro compound
  • C-nitro compound
  • Carbonic acid derivative
  • Oxacycle
  • Alkanolamine
  • Carboxylic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot 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 Solubility0.065 g/LALOGPS
logP1.11ALOGPS
logP1.34ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.5ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area144.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity80.39 m³·mol⁻¹ChemAxon
Polarizability30.85 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
DeepCCS[M+H]+167.12430932474
DeepCCS[M-H]-164.76630932474
DeepCCS[M-2H]-199.05730932474
DeepCCS[M+Na]+174.10130932474
AllCCS[M+H]+174.332859911
AllCCS[M+H-H2O]+171.032859911
AllCCS[M+NH4]+177.532859911
AllCCS[M+Na]+178.432859911
AllCCS[M-H]-173.632859911
AllCCS[M+Na-2H]-173.032859911
AllCCS[M+HCOO]-172.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-HydroxydantroleneOC1N(\N=C\C2=CC=C(O2)C2=CC=C(C=C2)N(=O)=O)C(=O)N=C1O4045.6Standard polar33892256
5-HydroxydantroleneOC1N(\N=C\C2=CC=C(O2)C2=CC=C(C=C2)N(=O)=O)C(=O)N=C1O3196.1Standard non polar33892256
5-HydroxydantroleneOC1N(\N=C\C2=CC=C(O2)C2=CC=C(C=C2)N(=O)=O)C(=O)N=C1O3329.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hydroxydantrolene,1TMS,isomer #1C[Si](C)(C)OC1C(O)=NC(=O)N1/N=C/C1=CC=C(C2=CC=C([N+](=O)[O-])C=C2)O13416.7Semi standard non polar33892256
5-Hydroxydantrolene,1TMS,isomer #2C[Si](C)(C)OC1=NC(=O)N(/N=C/C2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1O3412.6Semi standard non polar33892256
5-Hydroxydantrolene,2TMS,isomer #1C[Si](C)(C)OC1=NC(=O)N(/N=C/C2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1O[Si](C)(C)C3369.5Semi standard non polar33892256
5-Hydroxydantrolene,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1C(O)=NC(=O)N1/N=C/C1=CC=C(C2=CC=C([N+](=O)[O-])C=C2)O13663.3Semi standard non polar33892256
5-Hydroxydantrolene,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC(=O)N(/N=C/C2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1O3687.7Semi standard non polar33892256
5-Hydroxydantrolene,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC(=O)N(/N=C/C2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1O[Si](C)(C)C(C)(C)C3842.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxydantrolene GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-6794000000-8cf2ef9b3183bca31ca82017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxydantrolene GC-MS (2 TMS) - 70eV, Positivesplash10-0nti-6542900000-861630727116de99c14f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxydantrolene 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 - 5-Hydroxydantrolene 10V, Positive-QTOFsplash10-001i-2109000000-ead47501e0cc8c67b0ab2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxydantrolene 20V, Positive-QTOFsplash10-02u0-1659000000-04f786f95110694331a02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxydantrolene 40V, Positive-QTOFsplash10-0006-9200000000-a50bdbd9a003516239e92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxydantrolene 10V, Negative-QTOFsplash10-0006-9213000000-92952110231970fb21112017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxydantrolene 20V, Negative-QTOFsplash10-0006-9001000000-672a8e2bb6f69b6123dc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxydantrolene 40V, Negative-QTOFsplash10-0006-9000000000-12c0ca375ddffe52ea9c2017-10-06Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9577331
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