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Showing metabocard for Solerol (HMDB0002173)

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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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002173 (Solerol)

  Mrv0541 02231219242D          

 10 10  0  0  0  0            999 V2000
   10.4060   -7.7623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2223   -6.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8675   -6.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8675   -5.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2223   -5.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4060   -4.2999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4178   -5.2880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0599   -6.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4178   -6.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9036   -7.4193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
Download

3D MOL for HMDB0002173 (Solerol)

HMDB0002173
     RDKit          3D
Solerol
 20 20  0  0  0  0  0  0  0  0999 V2000
   -1.5522   -2.5407   -0.3939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7534   -1.6824    0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3911   -0.6087    0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973    0.6832    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400    0.6527   -0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395    1.8697   -1.5552 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2923    0.5033   -0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4259    1.3580    0.8730 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6607   -0.9144    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5933   -1.8038   -0.2405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8489   -0.5027    1.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634   -0.8306    1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    1.4971    0.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1115    0.8563   -0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1591   -0.1449   -1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9839    2.1178   -1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0568    0.8577   -0.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2244    0.9303    1.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501   -1.0197    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5501   -1.2783   -0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10  2  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
M  END
Download

3D SDF for HMDB0002173 (Solerol)

  Mrv0541 02231219242D          

 10 10  0  0  0  0            999 V2000
   10.4060   -7.7623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2223   -6.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8675   -6.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8675   -5.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2223   -5.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4060   -4.2999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4178   -5.2880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0599   -6.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4178   -6.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9036   -7.4193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002173

> <DATABASE_NAME>
hmdb

> <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_KEY>
QFCPIZSGDXQFDK-UHFFFAOYSA-N

> <FORMULA>
C6H10O4

> <MOLECULAR_WEIGHT>
146.1412

> <EXACT_MASS>
146.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
13.640574603235596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,6-dihydroxyoxepan-2-one

> <ALOGPS_LOGP>
-1.18

> <JCHEM_LOGP>
-1.1111185783333335

> <ALOGPS_LOGS>
0.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.029365193006132

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.331015322940821

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1863277181032297

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
32.2331

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.04e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
solerole

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0002173 (Solerol)

HMDB0002173
     RDKit          3D
Solerol
 20 20  0  0  0  0  0  0  0  0999 V2000
   -1.5522   -2.5407   -0.3939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7534   -1.6824    0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3911   -0.6087    0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1973    0.6832    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400    0.6527   -0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395    1.8697   -1.5552 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2923    0.5033   -0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4259    1.3580    0.8730 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6607   -0.9144    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5933   -1.8038   -0.2405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8489   -0.5027    1.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634   -0.8306    1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    1.4971    0.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1115    0.8563   -0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1591   -0.1449   -1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9839    2.1178   -1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0568    0.8577   -0.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2244    0.9303    1.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501   -1.0197    1.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5501   -1.2783   -0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10  2  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
M  END
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PDB for HMDB0002173 (Solerol)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      19.425 -14.490   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      19.082 -12.988   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.286 -12.028   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.286 -10.488   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.082  -9.528   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      19.425  -8.026   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      17.580  -9.871   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      16.912 -11.258   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.580 -12.645   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.620 -13.849   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    2    8   10                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0002173 (Solerol)

COMPND    HMDB0002173
HETATM    1  O1  UNL     1      -1.552  -2.541  -0.394  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.753  -1.682   0.042  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.391  -0.609   0.836  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.197   0.683   0.084  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.040   0.653  -0.871  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.039   1.870  -1.555  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.292   0.503  -0.214  1.00  0.00           C  
HETATM    8  O3  UNL     1       1.426   1.358   0.873  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.661  -0.914   0.115  1.00  0.00           C  
HETATM   10  O4  UNL     1       0.593  -1.804  -0.240  1.00  0.00           O  
HETATM   11  H1  UNL     1      -0.849  -0.503   1.803  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.463  -0.831   1.007  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.113   1.497   0.797  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.111   0.856  -0.526  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.159  -0.145  -1.621  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.984   2.118  -1.682  1.00  0.00           H  
HETATM   17  H7  UNL     1       2.057   0.858  -0.969  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.224   0.930   1.723  1.00  0.00           H  
HETATM   19  H9  UNL     1       1.850  -1.020   1.215  1.00  0.00           H  
HETATM   20  H10 UNL     1       2.550  -1.278  -0.421  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4   11   12
CONECT    4    5   13   14
CONECT    5    6    7   15
CONECT    6   16
CONECT    7    8    9   17
CONECT    8   18
CONECT    9   10   19   20
END
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SMILES for HMDB0002173 (Solerol)

OC1CCC(=O)OCC1O
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INCHI for HMDB0002173 (Solerol)

InChI=1S/C6H10O4/c7-4-1-2-6(9)10-3-5(4)8/h4-5,7-8H,1-3H2
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View in JSmolView NMR AssignmentsView Stereo Labels
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
Biological locationSource
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
Predicted Chromatographic Properties
Spectra
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 ]