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Showing NP-Card for 4,7-dimethyl-hexahydro-3h-cyclopenta[c]pyran-1-one (NP0214587)

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Record Information
Version2.0
Created at2022-09-05 13:55:54 UTC
Updated at2022-09-05 13:55:54 UTC
NP-MRD IDNP0214587
Secondary Accession NumbersNone
Natural Product Identification
Common Name4,7-dimethyl-hexahydro-3h-cyclopenta[c]pyran-1-one
DescriptionDihydronepetalactone belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Dihydronepetalactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dihydronepetalactone has been detected, but not quantified in, herbs and spices and tea. 4,7-dimethyl-hexahydro-3h-cyclopenta[c]pyran-1-one is found in Actinidia polygama, Nepeta nepetella and Nepeta tuberosa. This could make dihydronepetalactone a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0214587 (4,7-dimethyl-hexahydro-3h-cyclopenta[c]pyran-1-one)


  Mrv0541 02241219032D          

 12 13  0  0  0  0            999 V2000
   -1.3495    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643    0.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1186   -1.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 12  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for NP0214587 (4,7-dimethyl-hexahydro-3h-cyclopenta[c]pyran-1-one)

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
    2.7092   -0.7475    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7630   -0.0334   -0.2583 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1212    1.3988   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0865    2.2804   -0.6013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250    1.8690   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0790    2.4420   -1.3017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598    0.7370    0.3147 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3812   -0.3828    0.1074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2888   -1.2084   -0.9977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7565   -1.0034   -0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9327    0.2105   -0.0042 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7063   -0.1557    1.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294   -1.3886    0.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1457   -1.3913    1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2769   -0.0293    1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969   -0.4649   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9270    1.5771   -1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6161    1.7103    0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5930    1.1260    1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -1.0488    1.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518   -2.2430   -0.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1011   -0.7645   -1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1851   -0.8889   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2529   -1.9054   -0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4613    0.9803   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7388    0.2667    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103    0.3024    2.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443   -1.2448    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  7 11  1  0
  2  8  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 11 25  1  6
 10 23  1  0
 10 24  1  0
  9 21  1  0
  9 22  1  0
  8 20  1  1
  7 19  1  1
  3 17  1  0
  3 18  1  0
  2 16  1  6
  1 13  1  0
  1 14  1  0
  1 15  1  0
M  END
Download

3D SDF for NP0214587 (4,7-dimethyl-hexahydro-3h-cyclopenta[c]pyran-1-one)


  Mrv0541 02241219032D          

 12 13  0  0  0  0            999 V2000
   -1.3495    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643    0.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1186   -1.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643   -0.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 12  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214587

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2C1C(=O)OCC2C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h6-9H,3-5H2,1-2H3

> <INCHI_KEY>
LSRNBGXEEKNZHN-UHFFFAOYSA-N

> <FORMULA>
C10H16O2

> <MOLECULAR_WEIGHT>
168.2328

> <EXACT_MASS>
168.115029756

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.79613491245533

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,7-dimethyl-octahydrocyclopenta[c]pyran-1-one

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
2.0569600303333333

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.078410768233683

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
45.851200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,7-dimethyl-hexahydro-3H-cyclopenta[c]pyran-1-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0214587 (4,7-dimethyl-hexahydro-3h-cyclopenta[c]pyran-1-one)

Download
PDB for NP0214587 (4,7-dimethyl-hexahydro-3h-cyclopenta[c]pyran-1-one)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.519   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.613   1.245   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.148   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.184   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.184   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.088  -2.713   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.613  -1.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.148  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.184  -1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.184  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.519   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.519  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    1    6    8                                                  
CONECT    8    3    7    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9                                                            
CONECT   11    4   12                                                       
CONECT   12    9   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0214587 (4,7-dimethyl-hexahydro-3h-cyclopenta[c]pyran-1-one)
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SMILES for NP0214587 (4,7-dimethyl-hexahydro-3h-cyclopenta[c]pyran-1-one)
CC1CCC2C1C(=O)OCC2C
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INCHI for NP0214587 (4,7-dimethyl-hexahydro-3h-cyclopenta[c]pyran-1-one)
InChI=1S/C10H16O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h6-9H,3-5H2,1-2H3
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View in JSmol
Synonyms
ValueSource
DihydronepetalactoneMeSH
Chemical FormulaC10H16O2
Average Mass168.2328 Da
Monoisotopic Mass168.11503 Da
IUPAC Name4,7-dimethyl-octahydrocyclopenta[c]pyran-1-one
Traditional Name4,7-dimethyl-hexahydro-3H-cyclopenta[c]pyran-1-one
CAS Registry NumberNot Available
SMILES
CC1CCC2C1C(=O)OCC2C
InChI Identifier
InChI=1S/C10H16O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h6-9H,3-5H2,1-2H3
InChI KeyLSRNBGXEEKNZHN-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Actinidia polygamaLOTUS Database
Nepeta nepetellaLOTUS Database
Nepeta tuberosaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentTerpene lactones  
Alternative Parents
Substituents
  • Terpene lactone
    • 

  • Iridoid-skeleton
    • 

  • Bicyclic monoterpenoid
    • 

  • Monoterpenoid
    • 

  • Delta valerolactone
    • 

  • Delta_valerolactone
    • 

  • Oxane
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.02ALOGPS
logP2.06ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.85 m³·mol⁻¹ChemAxon
Polarizability18.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035829  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014594  
KNApSAcK IDNot Available
Chemspider ID453111  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound519465  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]