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Showing NP-Card for Delta-Hexanolactone (NP0001181)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-17 15:44:23 UTC
NP-MRD IDNP0001181
Secondary Accession NumbersNone
Natural Product Identification
Common NameDelta-Hexanolactone
DescriptionD-Hexanolactone is the lactone of 5-hydroxy-Hexanoic acid. Lactones are internal esters that exist in equilibrium between their closed (lactone) and open (hydroxy acid) forms in an aqueous environment. The lactone/hydroxy acid ratio at equilibrium is pH-dependent, with the closed form being favored at lower pH values, and can be greatly influenced by structural features of the lactone such as the ring size, substituents on the ring and the presence of double bonds within the ring. Many drugs and endogenous compounds are lactones or hydroxy acids and an enzyme capable of catalyzing the interchange between the open and closed forms in vivo could have pronounced effects upon their biological activity and/or distribution. D-Hexanolactone is the substrate of paraoxonases (PON) in humans. Human PON1 hydrolyzes over 30 different lactones (cyclic esters) and catalyzes the reverse reaction (lactonization) of a broad range of hydroxy acids. Hydroxy acid lactonization or lactone hydrolysis is catalyzed until equilibrium between the open and closed forms is reached. (PMID 15772423 , 12963475 , 12963475 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001181 (Delta-Hexanolactone)

5-Hydroxyhexanoic acid lactone.mol
  Mrv1652305271900082D          

  8  8  0  0  0  0            999 V2000
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  2  0  0  0  0
  1  8  1  0  0  0  0
  5  8  1  0  0  0  0
M  END
Download

3D MOL for NP0001181 (Delta-Hexanolactone)

HMDB0000453
     RDKit          3D
delta-Hexanolactone
 18 18  0  0  0  0  0  0  0  0999 V2000
    2.0802    0.4916   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9178   -0.3702   -0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1909   -1.0340    0.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8464   -0.0785    1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856    0.0931   -0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1612    0.8640   -1.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7682    1.8291   -1.6128 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172    0.4642   -1.3978 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7015   -0.1857    0.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6115    0.8381   -0.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444    1.3128    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3783   -1.1262   -1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8678   -1.2758    1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3228   -1.9391    0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118   -0.4261    1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049    0.9007    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073   -0.9160   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016    0.5577    0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
M  END
Download

3D SDF for NP0001181 (Delta-Hexanolactone)

5-Hydroxyhexanoic acid lactone.mol
  Mrv1652305271900082D          

  8  8  0  0  0  0            999 V2000
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  2  0  0  0  0
  1  8  1  0  0  0  0
  5  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001181

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O2/c1-5-3-2-4-6(7)8-5/h5H,2-4H2,1H3

> <INCHI_KEY>
RZTOWFMDBDPERY-UHFFFAOYSA-N

> <FORMULA>
C6H10O2

> <MOLECULAR_WEIGHT>
114.1424

> <EXACT_MASS>
114.068079564

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.122193225175327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-methyloxan-2-one

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
1.010694995333333

> <ALOGPS_LOGS>
-0.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0409063905943965

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
29.327900000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexanolactone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001181 (Delta-Hexanolactone)

HMDB0000453
     RDKit          3D
delta-Hexanolactone
 18 18  0  0  0  0  0  0  0  0999 V2000
    2.0802    0.4916   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9178   -0.3702   -0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1909   -1.0340    0.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8464   -0.0785    1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856    0.0931   -0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1612    0.8640   -1.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7682    1.8291   -1.6128 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172    0.4642   -1.3978 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7015   -0.1857    0.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6115    0.8381   -0.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444    1.3128    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3783   -1.1262   -1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8678   -1.2758    1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3228   -1.9391    0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118   -0.4261    1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049    0.9007    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073   -0.9160   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016    0.5577    0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
M  END
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PDB for NP0001181 (Delta-Hexanolactone)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5-Hydroxyhexanoic acid lactone.mol                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    7    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5                                                            
CONECT    7    1                                                            
CONECT    8    1    5                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for NP0001181 (Delta-Hexanolactone)

COMPND    HMDB0000453
HETATM    1  C1  UNL     1       2.080   0.492  -0.099  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.918  -0.370  -0.605  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.191  -1.034   0.516  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.846  -0.078   1.068  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.886   0.093  -0.047  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.161   0.864  -1.088  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.768   1.829  -1.613  1.00  0.00           O  
HETATM    8  O2  UNL     1       0.117   0.464  -1.398  1.00  0.00           O  
HETATM    9  H1  UNL     1       2.702  -0.186   0.537  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.612   0.838  -0.998  1.00  0.00           H  
HETATM   11  H3  UNL     1       1.644   1.313   0.507  1.00  0.00           H  
HETATM   12  H4  UNL     1       1.378  -1.126  -1.266  1.00  0.00           H  
HETATM   13  H5  UNL     1       0.868  -1.276   1.365  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.323  -1.939   0.124  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.312  -0.426   1.995  1.00  0.00           H  
HETATM   16  H8  UNL     1      -0.305   0.901   1.203  1.00  0.00           H  
HETATM   17  H9  UNL     1      -2.107  -0.916  -0.502  1.00  0.00           H  
HETATM   18  H10 UNL     1      -2.802   0.558   0.300  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    8   12
CONECT    3    4   13   14
CONECT    4    5   15   16
CONECT    5    6   17   18
CONECT    6    7    7    8
END
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SMILES for NP0001181 (Delta-Hexanolactone)

CC1CCCC(=O)O1
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INCHI for NP0001181 (Delta-Hexanolactone)

InChI=1S/C6H10O2/c1-5-3-2-4-6(7)8-5/h5H,2-4H2,1H3
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View in JSmolView NMR Assignments
Synonyms
ValueSource
Δ-hexanolactoneGenerator
Epsilon-CaprolactoneHMDB
(RS)-delta-HexalactoneHMDB
5-HexanolideHMDB
5-Hydroxy-hexanoateHMDB
5-Hydroxy-hexanoic acidHMDB
5-Hydroxy-hexanoic acid lactoneHMDB
5-HydroxyhexanoateHMDB
5-Hydroxyhexanoic acidHMDB
5-Hydroxyhexanoic acid lactoneHMDB
6-Methyl-D-valerolactoneHMDB
6-MethylvalerolactoneHMDB
delta-CaprolactoneHMDB
delta-HexalactoneHMDB
delta-HexanolideHMDB
delta-Methyl-delta-valerolactoneHMDB
HexanolactoneHMDB
Tetrahydro-6-methyl-2H-pyran-2-oneHMDB
Chemical FormulaC6H10O2
Average Mass114.1424 Da
Monoisotopic Mass114.06808 Da
IUPAC Name6-methyloxan-2-one
Traditional Namehexanolactone
CAS Registry Number823-22-3
SMILES
CC1CCCC(=O)O1
InChI Identifier
InChI=1S/C6H10O2/c1-5-3-2-4-6(7)8-5/h5H,2-4H2,1H3
InChI KeyRZTOWFMDBDPERY-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 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 NMR13C NMR Spectrum (1D, 50 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 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 NMR13C NMR Spectrum (1D, 176 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 NMR13C NMR Spectrum (1D, 226 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
Cocos nuciferaKNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
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
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point31.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point110.00 to 112.00 °C. @ 15.00 mm HgThe Good Scents Company Information System
Water Solubility32190 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.431 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility24.1 g/LALOGPS
logP0.93ALOGPS
logP1.01ChemAxon
logS-0.68ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity29.33 m³·mol⁻¹ChemAxon
Polarizability12.12 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000453
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008077
KNApSAcK IDC00054812
Chemspider ID12649
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5442
PubChem Compound13204
PDB IDNot Available
ChEBI ID589927
Good Scents IDrw1026381
References
General References
  1. Wang X, Zhang Q, Jia Z: A new tricyclic-alpha,beta-unsaturate ketone and a new delta-hexano lactone glycoside from Adenocaulon himalaicum. Nat Prod Res. 2007 Feb;21(2):161-6. doi: 10.1080/14786410601130000. [PubMed:17365704 ]