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Record Information
Version3.6
Creation Date2013-07-04 18:58:44 UTC
Update Date2017-03-02 22:05:24 UTC
HMDB IDHMDB60776
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Hydroxydantrolene
Description5-Hydroxydantrolene is a metabolite of dantrolene. 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. (Wikipedia)
Structure
Thumb
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
DescriptionThis compound belongs to the class of chemical entities known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassAzolidines
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
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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
Water Solubility0.065 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity80.39 m3·mol-1ChemAxon
Polarizability30.85 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00751
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB60776
      Metagene LinkHMDB60776
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available