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Showing metabocard for Mevalonolactone (HMDB0006024)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 20:29:11 UTC
Update Date2023-02-21 17:17:12 UTC
HMDB IDHMDB0006024
Secondary Accession Numbers
  • HMDB0011647
  • HMDB06024
  • HMDB11647
Metabolite Identification
Common NameMevalonolactone
DescriptionMevalonolactone is a substance obtained by the dehydration of mevalonic acid and is rapidly converted back into mevalonic acid in water. Mevaolonic acid exists in equilibrium with mevalolactone, which is formed by internal condensation of mevalonic acid's terminal alcohol and carboxylic acid functional groups. Mevalonic acid is a key intermediate in the biosynthesis of terpenes and steroids. Mevalonolactone is known ot inhibit HMG-CoA reductase activity.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006024 (Mevalonolactone)

  Mrv1652305271900222D          

  9  9  0  0  1  0            999 V2000
   13.2746   -4.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8621   -3.9423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1475   -4.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4331   -3.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4331   -3.1173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1475   -2.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1475   -1.8798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8621   -3.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6871   -3.9423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
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3D MOL for HMDB0006024 (Mevalonolactone)

HMDB0006024
     RDKit          3D
Mevalonolactone
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.4929   -0.9505    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6317   -0.1394   -0.2758 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3750    0.2035   -1.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    1.0456    0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2097    1.5546   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1703    0.5125    0.1367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7411   -0.7717   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3970   -1.7234    0.4408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4955   -1.0509   -0.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2256   -1.5626    0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7590   -1.5457    1.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0052   -0.2228    1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461    0.7937   -1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0559    0.7238    1.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8720    1.8361    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486    1.8992   -1.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5260    2.3708    0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6766   -0.8782   -1.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2078   -2.0949   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  9 18  1  0
  9 19  1  0
M  END
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3D SDF for HMDB0006024 (Mevalonolactone)

  Mrv1652305271900222D          

  9  9  0  0  1  0            999 V2000
   13.2746   -4.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8621   -3.9423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1475   -4.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4331   -3.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4331   -3.1173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1475   -2.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1475   -1.8798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8621   -3.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6871   -3.9423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006024

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@]1(O)CCOC(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3/t6-/m0/s1

> <INCHI_KEY>
JYVXNLLUYHCIIH-LURJTMIESA-N

> <FORMULA>
C6H10O3

> <MOLECULAR_WEIGHT>
130.1418

> <EXACT_MASS>
130.062994186

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
12.752369788944371

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-hydroxy-4-methyloxan-2-one

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-0.4289084339999999

> <ALOGPS_LOGS>
0.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.714889435349804

> <JCHEM_PKA_STRONGEST_BASIC>
-2.923507360977996

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
31.0192

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.11e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-hydroxy-4-methyloxan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0006024 (Mevalonolactone)

HMDB0006024
     RDKit          3D
Mevalonolactone
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.4929   -0.9505    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6317   -0.1394   -0.2758 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3750    0.2035   -1.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    1.0456    0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2097    1.5546   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1703    0.5125    0.1367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7411   -0.7717   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3970   -1.7234    0.4408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4955   -1.0509   -0.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2256   -1.5626    0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7590   -1.5457    1.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0052   -0.2228    1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461    0.7937   -1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0559    0.7238    1.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8720    1.8361    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486    1.8992   -1.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5260    2.3708    0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6766   -0.8782   -1.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2078   -2.0949   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  9 18  1  0
  9 19  1  0
M  END
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PDB for HMDB0006024 (Mevalonolactone)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      24.779  -8.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.009  -7.359   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.675  -8.129   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.342  -7.359   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      21.342  -5.819   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      22.675  -5.049   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      22.675  -3.509   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      24.009  -5.819   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      25.549  -7.359   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8    9                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    2    6                                                       
CONECT    9    2                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0006024 (Mevalonolactone)

COMPND    HMDB0006024
HETATM    1  C1  UNL     1       1.493  -0.950   0.703  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.632  -0.139  -0.276  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.375   0.204  -1.399  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.121   1.046   0.477  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.210   1.555  -0.035  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.170   0.512   0.137  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.741  -0.772  -0.030  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.397  -1.723   0.441  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.495  -1.051  -0.769  1.00  0.00           C  
HETATM   10  H1  UNL     1       2.226  -1.563   0.181  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.759  -1.546   1.307  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.005  -0.223   1.351  1.00  0.00           H  
HETATM   13  H4  UNL     1       2.146   0.794  -1.174  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.056   0.724   1.531  1.00  0.00           H  
HETATM   15  H6  UNL     1       0.872   1.836   0.503  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.149   1.899  -1.081  1.00  0.00           H  
HETATM   17  H8  UNL     1      -1.526   2.371   0.643  1.00  0.00           H  
HETATM   18  H9  UNL     1      -0.677  -0.878  -1.853  1.00  0.00           H  
HETATM   19  H10 UNL     1      -0.208  -2.095  -0.656  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    4    9
CONECT    3   13
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   18   19
END
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SMILES for HMDB0006024 (Mevalonolactone)

C[C@]1(O)CCOC(=O)C1
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INCHI for HMDB0006024 (Mevalonolactone)

InChI=1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3/t6-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(+/-) tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-oneHMDB
(1)-tetrahydro-4-Hydroxy-4-methyl-2H-pyran-2-oneHMDB
Divalonic acidHMDB
DL-Mevalonic acid lactoneHMDB
DL-MevalonolactoneHMDB
Mevalonic acid lactoneHMDB, MeSH
tetrahydro-4-Hydroxy-4-methyl-2H-pyran-2-oneHMDB
Mevalonolactone, (+-)-isomerMeSH, HMDB
Mevalonolactone, (S)-isomerMeSH, HMDB
Mevalonolactone, 3-(14)C-labeledMeSH, HMDB
Mevalonolactone, (R)-isomerMeSH, HMDB
Chemical FormulaC6H10O3
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
IUPAC Name(4S)-4-hydroxy-4-methyloxan-2-one
Traditional Name(4S)-4-hydroxy-4-methyloxan-2-one
CAS Registry Number503-48-0
SMILES
C[C@]1(O)CCOC(=O)C1
InChI Identifier
InChI=1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3/t6-/m0/s1
InChI KeyJYVXNLLUYHCIIH-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassDelta valerolactones
Direct ParentDelta valerolactones
Alternative Parents
Substituents
  • Delta_valerolactone
  • Delta valerolactone
  • Oxane
  • Tertiary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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 PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.0 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023804
KNApSAcK IDNot Available
Chemspider ID4483406
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5325923
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDMVLAC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available