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Showing NP-Card for (+)-isopiperitenone (NP0208222)

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Record Information
Version2.0
Created at2022-09-05 05:08:26 UTC
Updated at2022-09-05 05:08:26 UTC
NP-MRD IDNP0208222
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-isopiperitenone
Description(+)-Isopiperitenone belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. (+)-isopiperitenone is found in Tyrophagus similis and Zanthoxylum schinifolium. (+)-isopiperitenone was first documented in 2015 (PMID: 26220851). Based on a literature review a small amount of articles have been published on (+)-isopiperitenone (PMID: 34895548) (PMID: 29979593) (PMID: 27587903) (PMID: 27411040).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0208222 ((+)-isopiperitenone)


  Mrv1652309052207082D          

 11 11  0  0  1  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  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   -0.0000    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for NP0208222 ((+)-isopiperitenone)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.0129    1.6619    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571    0.4269   -0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -0.5597    0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220    0.0348   -0.8718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1512   -1.2067   -0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3504   -1.2583   -0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9861   -0.0210    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2122   -0.1288    0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437    1.1756   -0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2200    1.1641   -0.9531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0072    2.1430   -1.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331    2.3824    0.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9132    1.9360    0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9847   -1.3045   -0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562   -1.0978    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0070   -0.0499    0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0485   -0.2317   -1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4760   -1.2857    0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5529   -2.0865   -0.8078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7366   -2.1301    0.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5696   -1.3216   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8122   -1.0254    0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8388    0.7963    0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9247   -0.0928    2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8700    2.0795    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10  4  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  1 12  1  0
  1 13  1  0
  4 17  1  6
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
M  END
Download

3D SDF for NP0208222 ((+)-isopiperitenone)


  Mrv1652309052207082D          

 11 11  0  0  1  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  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   -0.0000    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0208222

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CCC(C)=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6,9H,1,4-5H2,2-3H3/t9-/m0/s1

> <INCHI_KEY>
SEZLYIWMVRUIKT-VIFPVBQESA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.221

> <EXACT_MASS>
150.104465071

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.630454572382

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-one

> <JCHEM_LOGP>
2.6563072546666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.706653704488513

> <JCHEM_PKA_STRONGEST_BASIC>
-4.653652941676497

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
47.124300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
isopiperitenone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0208222 ((+)-isopiperitenone)

Download
PDB for NP0208222 ((+)-isopiperitenone)
HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0208222 ((+)-isopiperitenone)
Download
SMILES for NP0208222 ((+)-isopiperitenone)
CC(=C)[C@@H]1CCC(C)=CC1=O
Download
INCHI for NP0208222 ((+)-isopiperitenone)
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6,9H,1,4-5H2,2-3H3/t9-/m0/s1
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View in JSmol
Synonyms
ValueSource
IsopiperitenoneChEBI
Chemical FormulaC10H14O
Average Mass150.2210 Da
Monoisotopic Mass150.10447 Da
IUPAC Name(6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional Nameisopiperitenone
CAS Registry NumberNot Available
SMILES
CC(=C)[C@@H]1CCC(C)=CC1=O
InChI Identifier
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6,9H,1,4-5H2,2-3H3/t9-/m0/s1
InChI KeySEZLYIWMVRUIKT-VIFPVBQESA-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
Tyrophagus similisLOTUS Database
Zanthoxylum schinifoliumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentMenthane monoterpenoids  
Alternative Parents
Substituents
  • P-menthane monoterpenoid
    • 

  • Monocyclic monoterpenoid
    • 

  • Cyclohexenone
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
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
logP2.66ChemAxon
pKa (Strongest Acidic)17.71ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.12 m³·mol⁻¹ChemAxon
Polarizability17.63 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00050980  
Chemspider ID388762  
KEGG Compound IDC02289  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439696  
PDB IDNot Available
ChEBI ID6041  
Good Scents IDrw1031161  
References
General References
  1. Srividya N, Lange I, Richter JK, Wust M, Lange BM: Selectivity of enzymes involved in the formation of opposite enantiomeric series of p-menthane monoterpenoids in peppermint and Japanese catnip. Plant Sci. 2022 Jan;314:111119. doi: 10.1016/j.plantsci.2021.111119. Epub 2021  Nov 18. [PubMed:34895548  ] 
  2. Cheallaigh AN, Mansell DJ, Toogood HS, Tait S, Lygidakis A, Scrutton NS, Gardiner JM: Chemoenzymatic Synthesis of the Intermediates in the Peppermint Monoterpenoid Biosynthetic Pathway. J Nat Prod. 2018 Jul 27;81(7):1546-1552. doi: 10.1021/acs.jnatprod.7b01026. Epub  2018 Jul 6. [PubMed:29979593  ] 
  3. Lygidakis A, Karuppiah V, Hoeven R, Ni Cheallaigh A, Leys D, Gardiner JM, Toogood HS, Scrutton NS: Pinpointing a Mechanistic Switch Between Ketoreduction and "Ene" Reduction in Short-Chain Dehydrogenases/Reductases. Angew Chem Weinheim Bergstr Ger. 2016 Aug 8;128(33):9748-9752. doi:  10.1002/ange.201603785. Epub 2016 Jul 13. [PubMed:27587903  ] 
  4. Lygidakis A, Karuppiah V, Hoeven R, Ni Cheallaigh A, Leys D, Gardiner JM, Toogood HS, Scrutton NS: Pinpointing a Mechanistic Switch Between Ketoreduction and "Ene" Reduction in Short-Chain Dehydrogenases/Reductases. Angew Chem Int Ed Engl. 2016 Aug 8;55(33):9596-600. doi: 10.1002/anie.201603785.  Epub 2016 Jul 13. [PubMed:27411040  ] 
  5. Qadri M, Deshidi R, Shah BA, Bindu K, Vishwakarma RA, Riyaz-Ul-Hassan S: An endophyte of Picrorhiza kurroa Royle ex. Benth, producing menthol, phenylethyl alcohol and 3-hydroxypropionic acid, and other volatile organic compounds. World J Microbiol Biotechnol. 2015 Oct;31(10):1647-54. doi:  10.1007/s11274-015-1910-6. Epub 2015 Jul 29. [PubMed:26220851  ] 
  6. LOTUS database [Link]