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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:39 UTC
Update Date2019-07-23 05:45:21 UTC
HMDB IDHMDB0002173
Secondary Accession Numbers
  • HMDB02173
Metabolite Identification
Common NameSolerol
DescriptionSolerol is a volatile component identified in extracts of grape wines and numerous fruits, with aroma being among the most important factors in determining wine character and quality. (PMID: 11052736 ). Solerol (4,5-dihydroxyhexanoic acid lactone) also appears to be a marker for Succinic semialdehyde dehydrogenase (SSADH) deficiency and probably arises from the reaction of succinic semialdehyde with an intermediate in the pyruvate dehydrogenase pathway (PMID: 3126356 ). SSADH is a defect in gamma-aminobutyric acid catabolism, resulting in the accumulation of gamma-hydroxybutyric acid (GHB) and causing neurological and cognitive disorders of varying severity.
Structure
Data?1563860721
Synonyms
ValueSource
4,5-DihydroxyhexanoateHMDB
4,5-Dihydroxyhexanoic acidHMDB
4,5-Dihydroxyhexanoic acid lactoneHMDB
4,5-Dihydroxyhexanoic acid-g-lactoneHMDB
4,5-Dihydroxyhexanoic acid-gamma-lactoneHMDB
Dihydro-5-(1-hydroxyethyl)-2(3H)-furanoneHMDB
Chemical FormulaC6H10O4
Average Molecular Weight146.1412
Monoisotopic Molecular Weight146.057908808
IUPAC Name5,6-dihydroxyoxepan-2-one
Traditional Namesolerole
CAS Registry Number27610-27-1
SMILES
OC1CCC(=O)OCC1O
InChI Identifier
InChI=1S/C6H10O4/c7-4-1-2-6(9)10-3-5(4)8/h4-5,7-8H,1-3H2
InChI KeyQFCPIZSGDXQFDK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassNot Available
Direct ParentLactones
Alternative Parents
Substituents
  • Caprolactone
  • Oxepane
  • 1,2-diol
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility804 g/LALOGPS
logP-1.2ALOGPS
logP-1.1ChemAxon
logS0.74ALOGPS
pKa (Strongest Acidic)13.33ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.23 m³·mol⁻¹ChemAxon
Polarizability13.64 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9200000000-4c970f40f73e58f9971eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0gk9-5690000000-02dfab8d541737d5816fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-1900000000-f0da1cd33e0a89590303JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-4900000000-4ee8f2053b2708df1351JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap0-9100000000-905eb8b9c2fa3f5bd816JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-e73f6fc151da3a771b0cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-3900000000-d8df955390befe22fbdeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e66e7f28804f18fb65c1JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    UrineDetected but not Quantified Not AvailableNot AvailableSuccinic semialdehyde dehydrogenase deficiency details
    Associated Disorders and Diseases
    Disease References
    Succinic semialdehyde dehydrogenase deficiency
    1. Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]
    Associated OMIM IDs
    • 271980 (Succinic semialdehyde dehydrogenase deficiency)
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022885
    KNApSAcK IDNot Available
    Chemspider ID13628309
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID6526
    PubChem Compound21252275
    PDB IDNot Available
    ChEBI ID89760
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceHoekman, Mark J.; Fagan, Gian L.; Webb, A. Dinsmoor; Kepner, Richard E. Synthesis of homologs of 4,5-dihydroxy- and 4-hydroxy-5-oxohexanoic acid g-lactones. Journal of Agricultural and Food Chemistry (1982), 30(5), 920-4.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Rocha S, Coutinho P, Barros A, Coimbra MA, Delgadillo I, Dias Cardoso A: Aroma potential of two bairrada white grape varieties: Maria Gomes and Bical. J Agric Food Chem. 2000 Oct;48(10):4802-7. [PubMed:11052736 ]
    2. Brown GK, Cromby CH, Manning NJ, Pollitt RJ: Urinary organic acids in succinic semialdehyde dehydrogenase deficiency: evidence of alpha-oxidation of 4-hydroxybutyric acid, interaction of succinic semialdehyde with pyruvate dehydrogenase and possible secondary inhibition of mitochondrial beta-oxidation. J Inherit Metab Dis. 1987;10(4):367-75. [PubMed:3126356 ]