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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:39 UTC
Update Date2022-03-07 02:49:13 UTC
HMDB IDHMDB0002173
Secondary Accession Numbers
  • HMDB02173
Metabolite Identification
Common NameSolerol
DescriptionSolerol, also known as 4,5-dihydroxyhexanoic acid lactone, is a volatile component originally 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 disorder that arises from a defect in gamma-aminobutyric acid catabolism, resulting in the accumulation of gamma-hydroxybutyric acid (GHB), 2,4-dihydroxybutyric acid, adipic acid as well as elevated levels of 4,5-dihydroxyhexanoic acid, and 4,5-dihydroxyhexanoic acid lactone and causing neurological and cognitive disorders of varying severity (PMID: 3126356 ). Children with SSADH deficiency usually manifest with developmental delay, behavioral symptoms, language dysfunction, seizures, hypotonia, extrapyramidal symptoms, and ataxia (PMID: 32055132 ).
Structure
Data?1612814165
Synonyms
ValueSource
SoleroleHMDB
4,5-Dihydroxyhexanoic acid-γ-lactoneHMDB
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point338.00 to 339.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.65331661259
DarkChem[M-H]-126.02431661259
DeepCCS[M+H]+129.30630932474
DeepCCS[M-H]-127.16730932474
DeepCCS[M-2H]-163.39930932474
DeepCCS[M+Na]+138.06130932474
AllCCS[M+H]+132.132859911
AllCCS[M+H-H2O]+127.532859911
AllCCS[M+NH4]+136.532859911
AllCCS[M+Na]+137.832859911
AllCCS[M-H]-126.932859911
AllCCS[M+Na-2H]-128.532859911
AllCCS[M+HCOO]-130.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SolerolOC1CCC(=O)OCC1O3329.6Standard polar33892256
SolerolOC1CCC(=O)OCC1O1386.6Standard non polar33892256
SolerolOC1CCC(=O)OCC1O1486.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Solerol,1TMS,isomer #1C[Si](C)(C)OC1CCC(=O)OCC1O1556.0Semi standard non polar33892256
Solerol,1TMS,isomer #2C[Si](C)(C)OC1COC(=O)CCC1O1574.3Semi standard non polar33892256
Solerol,2TMS,isomer #1C[Si](C)(C)OC1CCC(=O)OCC1O[Si](C)(C)C1646.7Semi standard non polar33892256
Solerol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCC(=O)OCC1O1816.3Semi standard non polar33892256
Solerol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1COC(=O)CCC1O1822.5Semi standard non polar33892256
Solerol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCC(=O)OCC1O[Si](C)(C)C(C)(C)C2080.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Solerol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9200000000-4c970f40f73e58f9971e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Solerol GC-MS (2 TMS) - 70eV, Positivesplash10-0gk9-5690000000-02dfab8d541737d5816f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Solerol 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 - Solerol 10V, Positive-QTOFsplash10-002b-1900000000-f0da1cd33e0a895903032016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solerol 20V, Positive-QTOFsplash10-002b-4900000000-4ee8f2053b2708df13512016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solerol 40V, Positive-QTOFsplash10-0ap0-9100000000-905eb8b9c2fa3f5bd8162016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solerol 10V, Negative-QTOFsplash10-0002-1900000000-e73f6fc151da3a771b0c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solerol 20V, Negative-QTOFsplash10-002b-3900000000-d8df955390befe22fbde2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solerol 40V, Negative-QTOFsplash10-0a4l-9000000000-e66e7f28804f18fb65c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solerol 10V, Negative-QTOFsplash10-06rb-9800000000-1689bfe8ea052b9a30da2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solerol 20V, Negative-QTOFsplash10-0a4i-9300000000-f2e635a0beec9e7988b22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solerol 40V, Negative-QTOFsplash10-0a4l-9000000000-4ab08fecdbc70f7d2a292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solerol 10V, Positive-QTOFsplash10-004i-2900000000-37fd96e4bae9be6114ea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solerol 20V, Positive-QTOFsplash10-056s-9700000000-e46015afa96bc6c367042021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Solerol 40V, Positive-QTOFsplash10-052f-9000000000-ebe5150e09325866136b2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot 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
FooDB 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
MarkerDB IDNot Available
Good Scents IDrw1603301
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. 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 ]
  2. 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 ]
  3. Yoganathan S, Arunachal G, Kratz L, Varman M, Thomas M, Sudhakar SV, Oommen SP, Danda S: Metabolic Stroke: A Novel Presentation in a Child with Succinic Semialdehyde Dehydrogenase Deficiency. Ann Indian Acad Neurol. 2020 Jan-Feb;23(1):113-117. doi: 10.4103/aian.AIAN_213_18. [PubMed:32055132 ]