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Showing NP-Card for Mevalonolactone (NP0000255)

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Record Information
Version1.0
Created at2007-04-12 20:29:11 UTC
Updated at2020-11-24 22:14:04 UTC
NP-MRD IDNP0000255
Secondary Accession NumbersNone
Natural Product 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 NP0000255 (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
Download

3D MOL for NP0000255 (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
Download

3D SDF for NP0000255 (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>
NP0000255

> <DATABASE_NAME>
NP-MRD

> <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 NP0000255 (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
Download

PDB for NP0000255 (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 NP0000255 (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 NP0000255 (Mevalonolactone)

C[C@]1(O)CCOC(=O)C1
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INCHI for NP0000255 (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 Assignments
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
Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-oneHMDB
Mevalonolactone, (+-)-isomerHMDB
Mevalonolactone, (S)-isomerHMDB
Mevalonolactone, 3-(14)C-labeledHMDB
Mevalonolactone, (R)-isomerHMDB
Chemical FormulaC6H10O3
Average Mass130.1418 Da
Monoisotopic Mass130.06299 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Penicillium herqueiLOTUS Database
Phaeosphaeria herpotrichoidesLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
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 Solubility311 g/LALOGPS
logP-0.14ALOGPS
logP-0.43ChemAxon
logS0.38ALOGPS
pKa (Strongest Acidic)14.71ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.02 m³·mol⁻¹ChemAxon
Polarizability12.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006024
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
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