NP-MRD: Showing NP-Card for nepetaparnone (NP0328654)

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Record Information

Version

2.0

Created at

2022-09-12 12:19:06 UTC

Updated at

2022-09-12 12:19:06 UTC

NP-MRD ID

NP0328654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nepetaparnone

Description

Nepetaparnone belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. nepetaparnone was first documented in 2008 (PMID: 18393463). Based on a literature review very few articles have been published on nepetaparnone (PMID: 25978278).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          2D

 48 52  0  0  0  0  0  0  0  0999 V2000
    3.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135   -2.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -3.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135   -2.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9635   -4.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    1.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2384    2.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873    2.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004    3.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4373    0.8999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0490   -0.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001   -0.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3130   -1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499    1.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6478    1.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1853    2.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0196    3.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0756    4.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1828   -1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3630    1.4554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6480   -2.2871    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9635   -4.0247    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0037   -4.7220    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8603   -4.8361    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838   -2.1155    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135   -5.3237    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2626   -3.2747    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7656   -4.9274    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920    2.3780    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391   -1.4622    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9110   -2.7265    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207   -2.5248    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3828   -0.2994    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396    1.2166    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598   -0.4075    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0023    3.7181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5949    1.9471    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0803    4.4647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8683    5.7355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2414    5.5138    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0901    3.6258    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  8  9  1  6
  8 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 13 14  1  1
 13 23  1  0
 23 24  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  2  0
 18 19  1  0
  8  6  1  0
 18 17  1  0
  8  3  1  0
 20 13  1  0
 13 12  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  6 32  1  1
  5 30  1  0
  5 31  1  0
  4 28  1  0
  4 29  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 12 36  1  1
 17 37  1  1
 23 45  1  1
 24 46  1  0
 24 47  1  0
 24 48  1  0
 22 43  1  0
 22 44  1  0
 21 41  1  0
 21 42  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END


  Mrv1652309122214192D          

 24 28  0  0  1  0            999 V2000
    5.0655    0.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7545    0.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4228   -0.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2629   -0.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6977   -1.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2430   -1.8522    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5242   -2.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4332   -1.6004    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7615   -1.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -1.3523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3381   -0.5453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8074    0.0114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1294   -0.6466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7736   -1.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5903   -0.9741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2005   -1.7518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7693   -2.2690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8096   -2.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4978   -3.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -1.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3107   -1.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8598   -1.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3076   -0.4286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0051    0.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  3  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 17 16  1  6  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 13 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0328654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCC2=C(C)[C@@H]3OC(=O)[C@@]12[C@@H]1OC(=O)[C@@]32[C@H](C)CCC2=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/c1-9-5-7-13-11(3)16-20-10(2)6-8-14(20)12(4)15(23-18(20)22)19(9,13)17(21)24-16/h9-10,15-16H,5-8H2,1-4H3/t9-,10+,15+,16-,19-,20+

> <INCHI_KEY>
KESCUBFFLAUUPO-VUESOCQISA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.408

> <EXACT_MASS>
328.167459253

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
30.42402128119339

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,7S,8S,9R,14R)-3,7,10,14-tetramethyl-16,18-dioxapentacyclo[7.5.2.2^{2,8}.0^{1,11}.0^{4,8}]octadeca-3,10-diene-15,17-dione

> <JCHEM_LOGP>
3.078527476666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.919276042596133

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
88.0844

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,7S,8S,9R,14R)-3,7,10,14-tetramethyl-16,18-dioxapentacyclo[7.5.2.2^{2,8}.0^{1,11}.0^{4,8}]octadeca-3,10-diene-15,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       9.456   1.455   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.875   0.029   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.123  -1.198   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.691  -0.809   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.502  -2.143   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.654  -3.458   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.179  -4.905   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.142  -2.987   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.888  -2.253   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.372  -2.524   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.098  -1.018   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.107   0.021   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.842  -1.207   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.044  -2.036   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.569  -1.818   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.841  -3.270   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.903  -4.236   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.111  -4.251   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.529  -5.677   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.868  -3.012   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.313  -3.446   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.472  -2.131   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.307  -0.800   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.743   0.633   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    3    9   17                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    2   13                                                  
CONECT   13   12   14   20   23                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   13   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₄

Average Mass

328.4080 Da

Monoisotopic Mass

328.16746 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC2=C(C)[C@@H]3OC(=O)[C@@]12[C@@H]1OC(=O)[C@@]32[C@H](C)CCC2=C1C

InChI Identifier

InChI=1S/C20H24O4/c1-9-5-7-13-11(3)16-20-10(2)6-8-14(20)12(4)15(23-18(20)22)19(9,13)17(21)24-16/h9-10,15-16H,5-8H2,1-4H3/t9-,10+,15+,16-,19-,20+

InChI Key

KESCUBFFLAUUPO-VUESOCQISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Dicarboxylic acid or derivatives
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039844

Chemspider ID

24693816

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24879156

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jayan S, Jones PB: Photochemical Synthesis of Nepetanudone. J Nat Prod. 2015 Jun 26;78(6):1434-6. doi: 10.1021/np500832h. Epub 2015 May 15. [PubMed:25978278 ]
Gkinis G, Ioannou E, Quesada A, Vagias C, Tzakou O, Roussis V: Parnapimarol and nepetaparnone from Nepeta parnassica. J Nat Prod. 2008 May;71(5):926-8. doi: 10.1021/np800043b. Epub 2008 Apr 5. [PubMed:18393463 ]
LOTUS database [Link]

Showing NP-Card for nepetaparnone (NP0328654)

MOL for NP0328654 (nepetaparnone)

3D MOL for NP0328654 (nepetaparnone)

3D SDF for NP0328654 (nepetaparnone)

3D-SDF for NP0328654 (nepetaparnone)

PDB for NP0328654 (nepetaparnone)

3D PDB for NP0328654 (nepetaparnone)

SMILES for NP0328654 (nepetaparnone)

INCHI for NP0328654 (nepetaparnone)

Structure for NP0328654 (nepetaparnone)

3D Structure for NP0328654 (nepetaparnone)