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Showing NP-Card for (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one (NP0048261)

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Record Information
Version2.0
Created at2022-03-17 20:53:40 UTC
Updated at2022-03-17 20:53:40 UTC
NP-MRD IDNP0048261
Secondary Accession NumbersNone
Natural Product Identification
Common Name(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one
Description(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, also known as cis-jasmone or (Z)-jasmone, belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. Thus, (Z)-3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one is considered to be an octadecanoid lipid molecule (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one is a celery, floral, and herbal tasting compound. Outside of the human body, (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one is found, on average, in the highest concentration within a few different foods, such as spearmints, tea, and orange mints (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one has also been detected, but not quantified in, several different foods, such as herbs and spices, figs, citrus, sweet oranges, and peppermints. (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one is found in Achillea millefolium, Achillea ptarmica, Agastache rugosa, Ageratum conyzoides, Artemisia annua, Artemisia herba-alba, Artemisia judaica, Artemisia salsoloides, Basella alba, Citrus sinensis, Clinopodium serpyllifolium, Echinophora tenuifolia, Elsholtzia fruticosa, Flourensia cernua, Hypericum perforatum, Lonicera japonica, Monarda fistulosa, Nelumbo lutea, Paeonia lactiflora, Pectis elongata, Pulicaria arabica, Salvia cinnabarina, Salvia syriaca, Tagetes lucida and Vachellia rigidula. This could make (Z)-3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048261 ((Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one)


  Mrv0541 02241215502D          

 12 12  0  0  0  0            999 V2000
   -2.0920   -4.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594   -5.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5045   -5.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6795   -5.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4245   -5.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -3.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1945   -6.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6399   -4.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4684   -4.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162   -3.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9293   -4.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7578   -5.2173    0.0000 C   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
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
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3D MOL for NP0048261 ((Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one)

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3D SDF for NP0048261 ((Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one)

  Mrv0541 02241215502D          

 12 12  0  0  0  0            999 V2000
   -2.0920   -4.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594   -5.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5045   -5.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6795   -5.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4245   -5.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -3.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1945   -6.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6399   -4.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4684   -4.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162   -3.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9293   -4.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7578   -5.2173    0.0000 C   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
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048261

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/CC1=C(C)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4-

> <INCHI_KEY>
XMLSXPIVAXONDL-PLNGDYQASA-N

> <FORMULA>
C11H16O

> <MOLECULAR_WEIGHT>
164.2441

> <EXACT_MASS>
164.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.792559279979017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
3.0967138536666665

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.78438047953379

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
52.8994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
jasmone

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048261 ((Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one)
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PDB for NP0048261 ((Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-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      -3.905  -8.755   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.151  -9.660   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.675 -11.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.135 -11.125   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.659  -9.660   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.905  -7.215   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.230 -12.371   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.194  -9.184   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.874  -7.678   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.590  -7.202   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.735  -8.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.415  -9.739   0.000  0.00  0.00           C+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    1    8                                                  
CONECT    6    1                                                            
CONECT    7    4                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0048261 ((Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one)
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SMILES for NP0048261 ((Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one)
CC\C=C/CC1=C(C)CCC1=O
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INCHI for NP0048261 ((Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one)
InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4-
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Synonyms
ValueSource
cis-JasmoneKegg
(Z)-JasmoneHMDB
2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)- (8ci)HMDB
2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2-pentenyl- (9ci)HMDB
3-Methyl-2-[(2Z)-2-pentenyl]-2-cyclopenten-1-oneHMDB
cis-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-oneHMDB
JasmoneHMDB
(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-oneMeSH
Chemical FormulaC11H16O
Average Mass164.2441 Da
Monoisotopic Mass164.12012 Da
IUPAC Name3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
Traditional Namejasmone
CAS Registry Number488-10-8
SMILES
CC\C=C/CC1=C(C)CCC1=O
InChI Identifier
InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4-
InChI KeyXMLSXPIVAXONDL-PLNGDYQASA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea millefoliumLOTUS Database
Achillea ptarmicaLOTUS Database
Agastache rugosaLOTUS Database
Ageratum conyzoidesLOTUS Database
Artemisia annuaLOTUS Database
Artemisia herba-albaLOTUS Database
Artemisia judaicaLOTUS Database
Artemisia salsoloidesLOTUS Database
Basella albaLOTUS Database
Citrus reticulataFooDB
Citrus sinensisLOTUS Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clinopodium serpyllifoliumLOTUS Database
Echinophora tenuifoliaLOTUS Database
Elsholtzia fruticosaLOTUS Database
Ficus caricaFooDB
Flourensia cernuaLOTUS Database
Hypericum perforatumLOTUS Database
Lonicera japonicaLOTUS Database
Mentha aquaticaFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Monarda fistulosaLOTUS Database
Nelumbo luteaLOTUS Database
Paeonia lactifloraLOTUS Database
Pectis elongataLOTUS Database
Pulicaria arabicaLOTUS Database
Salvia cinnabarinaLOTUS Database
Salvia syriacaLOTUS Database
Tagetes lucidaLOTUS Database
Vachellia rigidulaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentCyclic ketones  
Alternative Parents
Substituents
  • Cyclic ketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP3.32ALOGPS
logP3.1ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.9 m³·mol⁻¹ChemAxon
Polarizability19.79 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035601  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014294  
KNApSAcK IDC00001313 C00029353  
Chemspider ID1266012  
KEGG Compound IDC08490  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1549018  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available