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Showing metabocard for Isopiperitenone (HMDB0302241)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 16:14:58 UTC
Update Date2021-09-23 16:14:58 UTC
HMDB IDHMDB0302241
Secondary Accession NumbersNone
Metabolite Identification
Common NameIsopiperitenone
DescriptionIsopiperitenone, also known as 3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-one or 6-isopropenyl-3-methyl-2-cyclohexen-1-one, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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 slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Isopiperitenone can be found in dill and spearmint, which makes isopiperitenone a potential biomarker for the consumption of these food products.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0302241 (Isopiperitenone)

  Mrv0541 02241221362D          

 11 11  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 O   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
    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
    0.0000    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 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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0302241 (Isopiperitenone)

HMDB0302241
     RDKit          3D
Isopiperitenone
 25 25  0  0  0  0  0  0  0  0999 V2000
    3.2035   -0.9418    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1243   -0.1741    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2947    1.3156    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7503   -0.7273   -0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0033   -0.5479    1.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665   -0.4223    1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9827    0.0849   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4177    0.4976   -0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830    0.2129   -1.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -0.1780   -1.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7953   -0.0429   -2.3794 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -2.0090   -0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955   -0.5358    0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3490    1.5792    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249    1.8605   -0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632    1.6510    1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8768   -1.8354   -0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4190    0.3669    1.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2658   -1.3922    1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -1.4004    1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8516    0.2606    1.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9686    0.1944    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5221    1.6088   -0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9505   -0.0178   -1.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333    0.5925   -2.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  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
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  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
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3D SDF for HMDB0302241 (Isopiperitenone)

  Mrv0541 02241221362D          

 11 11  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 O   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
    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
    0.0000    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 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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302241

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CCC(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

> <INCHI_KEY>
SEZLYIWMVRUIKT-UHFFFAOYSA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.2176

> <EXACT_MASS>
150.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
17.65874606489726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.6563072546666664

> <ALOGPS_LOGS>
-2.08

> <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>
47.12429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
p-mentha-1,8-dien-3-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0302241 (Isopiperitenone)

HMDB0302241
     RDKit          3D
Isopiperitenone
 25 25  0  0  0  0  0  0  0  0999 V2000
    3.2035   -0.9418    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1243   -0.1741    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2947    1.3156    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7503   -0.7273   -0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0033   -0.5479    1.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665   -0.4223    1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9827    0.0849   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4177    0.4976   -0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830    0.2129   -1.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084   -0.1780   -1.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7953   -0.0429   -2.3794 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -2.0090   -0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955   -0.5358    0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3490    1.5792    0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249    1.8605   -0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632    1.6510    1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8768   -1.8354   -0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4190    0.3669    1.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2658   -1.3922    1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -1.4004    1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8516    0.2606    1.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9686    0.1944    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5221    1.6088   -0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9505   -0.0178   -1.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333    0.5925   -2.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  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
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  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
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PDB for HMDB0302241 (Isopiperitenone)

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  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   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      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0302241 (Isopiperitenone)

COMPND    HMDB0302241
HETATM    1  C1  UNL     1       3.204  -0.942   0.019  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.124  -0.174   0.006  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.295   1.316   0.157  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.750  -0.727  -0.153  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.003  -0.548   1.119  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.466  -0.422   1.010  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.983   0.085  -0.259  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.418   0.498  -0.321  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.283   0.213  -1.373  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.108  -0.178  -1.345  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.795  -0.043  -2.379  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.103  -2.009  -0.087  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.195  -0.536   0.135  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.349   1.579   0.048  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.725   1.860  -0.633  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.963   1.651   1.175  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.877  -1.835  -0.342  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.419   0.367   1.626  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.266  -1.392   1.789  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.994  -1.400   1.213  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.852   0.261   1.824  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.969   0.194   0.592  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.522   1.609  -0.393  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.951  -0.018  -1.167  1.00  0.00           H  
HETATM   25  H14 UNL     1      -1.733   0.593  -2.262  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   10   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    9    9
CONECT    8   22   23   24
CONECT    9   10   25
CONECT   10   11   11
END
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SMILES for HMDB0302241 (Isopiperitenone)

CC(=C)C1CCC(C)=CC1=O
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INCHI for HMDB0302241 (Isopiperitenone)

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6,9H,1,4-5H2,2-3H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
6-Isopropenyl-3-methyl-2-cyclohexen-1-oneChEBI
IsopiperitenonChEBI
Iso-piperitenoneMeSH
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional Namep-mentha-1,8-dien-3-one
CAS Registry NumberNot Available
SMILES
CC(=C)C1CCC(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
InChI KeySEZLYIWMVRUIKT-UHFFFAOYSA-N
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
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003858
KNApSAcK IDC00050980
Chemspider ID71368
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID50110
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1031161
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available