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Showing metabocard for Polylimonene (HMDB0032473)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:59 UTC
Update Date2022-03-07 02:53:22 UTC
HMDB IDHMDB0032473
Secondary Accession Numbers
  • HMDB32473
Metabolite Identification
Common NamePolylimonene
DescriptionPolylimonene, also known as (+/-)-limonene or cajeputene, 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. Based on a literature review a significant number of articles have been published on Polylimonene.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032473 (Polylimonene)

limonene
  Mrv1572001071617222D          

 10 10  0  0  0  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  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
    0.7145   -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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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
  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
M  END
Download

3D MOL for HMDB0032473 (Polylimonene)

HMDB0032473
     RDKit          3D
Polylimonene
 26 26  0  0  0  0  0  0  0  0999 V2000
   -2.5191    0.8112   -1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0982   -0.0022   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0280   -1.0666    0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7402    0.1044    0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0465    1.3511   -0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3893    1.3365    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201    0.2312    0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5293    0.2569    0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284   -0.9438   -0.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1037   -1.1224    0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9423    1.6101   -1.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5522    0.6762   -1.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7596   -2.0652   -0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0744   -0.8639    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822   -1.1424    1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927    0.2587    1.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5284    2.2598    0.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0240    1.3991   -1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8164    2.2113    0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6285    0.1048    1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9829    1.2150    0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1004   -0.5618    0.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0564   -1.8257   -0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149   -0.7590   -1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5190   -1.8477   -0.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2366   -1.6256    1.1774 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10  4  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
M  END
Download

3D SDF for HMDB0032473 (Polylimonene)

limonene
  Mrv1572001071617222D          

 10 10  0  0  0  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  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
    0.7145   -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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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
  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
M  END
> <DATABASE_ID>
HMDB0032473

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CCC(C)=CC1

> <INCHI_IDENTIFIER>
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3

> <INCHI_KEY>
XMGQYMWWDOXHJM-UHFFFAOYSA-N

> <FORMULA>
C10H16

> <MOLECULAR_WEIGHT>
136.238

> <EXACT_MASS>
136.125200515

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.54813346687505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
3.2198126516666665

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
46.4803

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
limonene, (+)-

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0032473 (Polylimonene)

HMDB0032473
     RDKit          3D
Polylimonene
 26 26  0  0  0  0  0  0  0  0999 V2000
   -2.5191    0.8112   -1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0982   -0.0022   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0280   -1.0666    0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7402    0.1044    0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0465    1.3511   -0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3893    1.3365    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201    0.2312    0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5293    0.2569    0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284   -0.9438   -0.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1037   -1.1224    0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9423    1.6101   -1.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5522    0.6762   -1.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7596   -2.0652   -0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0744   -0.8639    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822   -1.1424    1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927    0.2587    1.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5284    2.2598    0.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0240    1.3991   -1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8164    2.2113    0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6285    0.1048    1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9829    1.2150    0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1004   -0.5618    0.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0564   -1.8257   -0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149   -0.7590   -1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5190   -1.8477   -0.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2366   -1.6256    1.1774 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10  4  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
M  END
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PDB for HMDB0032473 (Polylimonene)

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: limonene                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         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
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                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0032473 (Polylimonene)

COMPND    HMDB0032473
HETATM    1  C1  UNL     1      -2.519   0.811  -1.155  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.098  -0.002  -0.214  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.028  -1.067   0.299  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.740   0.104   0.340  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.047   1.351  -0.148  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.389   1.337   0.281  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.120   0.231   0.147  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.529   0.257   0.583  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.428  -0.944  -0.450  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.104  -1.122   0.187  1.00  0.00           C  
HETATM   11  H1  UNL     1      -1.942   1.610  -1.598  1.00  0.00           H  
HETATM   12  H2  UNL     1      -3.552   0.676  -1.534  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.760  -2.065  -0.109  1.00  0.00           H  
HETATM   14  H4  UNL     1      -4.074  -0.864   0.004  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.982  -1.142   1.403  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.893   0.259   1.455  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.528   2.260   0.232  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.024   1.399  -1.253  1.00  0.00           H  
HETATM   19  H9  UNL     1       1.816   2.211   0.690  1.00  0.00           H  
HETATM   20  H10 UNL     1       3.628   0.105   1.696  1.00  0.00           H  
HETATM   21  H11 UNL     1       3.983   1.215   0.277  1.00  0.00           H  
HETATM   22  H12 UNL     1       4.100  -0.562   0.082  1.00  0.00           H  
HETATM   23  H13 UNL     1       2.056  -1.826  -0.227  1.00  0.00           H  
HETATM   24  H14 UNL     1       1.315  -0.759  -1.533  1.00  0.00           H  
HETATM   25  H15 UNL     1      -0.519  -1.848  -0.411  1.00  0.00           H  
HETATM   26  H16 UNL     1       0.237  -1.626   1.177  1.00  0.00           H  
CONECT    1    2    2   11   12
CONECT    2    3    4
CONECT    3   13   14   15
CONECT    4    5   10   16
CONECT    5    6   17   18
CONECT    6    7    7   19
CONECT    7    8    9
CONECT    8   20   21   22
CONECT    9   10   23   24
CONECT   10   25   26
END
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SMILES for HMDB0032473 (Polylimonene)

CC(=C)C1CCC(C)=CC1
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INCHI for HMDB0032473 (Polylimonene)

InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H16
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
IUPAC Name1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
Traditional Namelimonene, (+)-
CAS Registry Number9003-73-0
SMILES
CC(=C)C1CCC(C)=CC1
InChI Identifier
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3
InChI KeyXMGQYMWWDOXHJM-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
  • Branched unsaturated hydrocarbon
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Source
ProcessNot Available
Role
Biological roleIndustrial application
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 Locations
  • Extracellular
  • Membrane
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 IDFDB014115
KNApSAcK IDC00003043
Chemspider ID20939
KEGG Compound IDC06078
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22311
PDB IDNot Available
ChEBI ID15384
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
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