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Showing metabocard for Perillic acid (HMDB0004586)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 21:42:07 UTC
Update Date2023-02-21 17:17:03 UTC
HMDB IDHMDB0004586
Secondary Accession Numbers
  • HMDB0006539
  • HMDB04586
  • HMDB06539
Metabolite Identification
Common NamePerillic acid
DescriptionPerillic acid, also known as perillate, 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. Perillic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004586 (Perillic acid)

Perillyl aldehyde metabolite 3
  Mrv1652309042000302D          

 12 12  0  0  0  0            999 V2000
    0.0000    0.8250    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   -0.4125    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   -0.4125    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   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
  6  5  1  0  0  0  0
  6  1  2  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  1  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
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3D MOL for HMDB0004586 (Perillic acid)

HMDB0004586
     RDKit          3D
Perillic acid
 26 26  0  0  0  0  0  0  0  0999 V2000
   -2.4548   -1.6810    0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0912   -0.4582   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1317    0.5925   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777   -0.0191   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2689   -1.1818   -0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -0.7189   -0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310    0.2950    0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3880    0.8173    0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6975    1.7718    1.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3316    0.2758   -0.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0522    0.8956    1.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3142    1.0557    0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5020   -1.9341    0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7635   -2.5104    0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5093    0.8880    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7966    1.4433   -0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9881    0.0866   -0.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6286    0.4337   -1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0342   -1.7978   -1.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1960   -1.8144    0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3829   -1.1480   -1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8381   -0.5820   -0.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0491    0.3198    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4131    1.9098    1.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454    0.9824    1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373    2.0785    0.2905 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
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12  4  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
 10 22  1  0
 11 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
M  END
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3D SDF for HMDB0004586 (Perillic acid)

Perillyl aldehyde metabolite 3
  Mrv1652309042000302D          

 12 12  0  0  0  0            999 V2000
    0.0000    0.8250    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   -0.4125    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   -0.4125    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   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
  6  5  1  0  0  0  0
  6  1  2  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  1  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004586

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)

> <INCHI_KEY>
CDSMSBUVCWHORP-UHFFFAOYSA-N

> <FORMULA>
C10H14O2

> <MOLECULAR_WEIGHT>
166.22

> <EXACT_MASS>
166.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.133603920265852

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.411505250666667

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.991443593247131

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
48.197500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
perillic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0004586 (Perillic acid)

HMDB0004586
     RDKit          3D
Perillic acid
 26 26  0  0  0  0  0  0  0  0999 V2000
   -2.4548   -1.6810    0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0912   -0.4582   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1317    0.5925   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777   -0.0191   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2689   -1.1818   -0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -0.7189   -0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310    0.2950    0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3880    0.8173    0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6975    1.7718    1.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3316    0.2758   -0.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0522    0.8956    1.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3142    1.0557    0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5020   -1.9341    0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7635   -2.5104    0.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5093    0.8880    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7966    1.4433   -0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9881    0.0866   -0.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6286    0.4337   -1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0342   -1.7978   -1.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1960   -1.8144    0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3829   -1.1480   -1.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8381   -0.5820   -0.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0491    0.3198    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4131    1.9098    1.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454    0.9824    1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373    2.0785    0.2905 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
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12  4  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
 10 22  1  0
 11 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
M  END
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PDB for HMDB0004586 (Perillic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Perillyl aldehyde metabolite 3                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -1.540   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      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   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       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   10    6    2                                                  
CONECT    2    3    1                                                       
CONECT    3    2    4                                                       
CONECT    4    8    5    3                                                  
CONECT    5    6    4                                                       
CONECT    6    5    1                                                       
CONECT    7    8                                                            
CONECT    8    4    7    9                                                  
CONECT    9    8                                                            
CONECT   10    1   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0004586 (Perillic acid)

COMPND    HMDB0004586
HETATM    1  C1  UNL     1      -2.455  -1.681   0.166  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.091  -0.458  -0.120  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.132   0.592  -0.300  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.678  -0.019  -0.285  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.269  -1.182  -0.274  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.658  -0.719  -0.398  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.031   0.295   0.373  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.388   0.817   0.315  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.698   1.772   1.057  1.00  0.00           O  
HETATM   10  O2  UNL     1       4.332   0.276  -0.544  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.052   0.896   1.298  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.314   1.056   0.705  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.502  -1.934   0.273  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.764  -2.510   0.315  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.509   0.888   0.713  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.797   1.443  -0.899  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.988   0.087  -0.833  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.629   0.434  -1.298  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.034  -1.798  -1.182  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.196  -1.814   0.623  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.383  -1.148  -1.070  1.00  0.00           H  
HETATM   22  H10 UNL     1       4.838  -0.582  -0.282  1.00  0.00           H  
HETATM   23  H11 UNL     1       1.049   0.320   2.259  1.00  0.00           H  
HETATM   24  H12 UNL     1       1.413   1.910   1.567  1.00  0.00           H  
HETATM   25  H13 UNL     1      -1.045   0.982   1.543  1.00  0.00           H  
HETATM   26  H14 UNL     1      -0.437   2.078   0.291  1.00  0.00           H  
CONECT    1    2    2   13   14
CONECT    2    3    4
CONECT    3   15   16   17
CONECT    4    5   12   18
CONECT    5    6   19   20
CONECT    6    7    7   21
CONECT    7    8   11
CONECT    8    9    9   10
CONECT   10   22
CONECT   11   12   23   24
CONECT   12   25   26
END
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SMILES for HMDB0004586 (Perillic acid)

CC(=C)C1CCC(=CC1)C(O)=O
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INCHI for HMDB0004586 (Perillic acid)

InChI=1S/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acidChEBI
4-Isopropenylcyclohex-1-enecarboxylic acidChEBI
4-(1-Methylethenyl)-1-cyclohexene-1-carboxylateGenerator
4-Isopropenylcyclohex-1-enecarboxylateGenerator
PerillateGenerator
4-(2-Propenyl)-1-cyclohexane-1-carboxylic acidHMDB
4-Isopropenylcyclohex-1-ene carboxylic acidHMDB
Chemical FormulaC10H14O2
Average Molecular Weight166.22
Monoisotopic Molecular Weight166.099379691
IUPAC Name4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid
Traditional Nameperillic acid
CAS Registry Number7694-45-3
SMILES
CC(=C)C1CCC(=CC1)C(O)=O
InChI Identifier
InChI=1S/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)
InChI KeyCDSMSBUVCWHORP-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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point60 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.428Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available124.925http://allccs.zhulab.cn/database/detail?ID=AllCCS00001265
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia		 details
BloodDetected and Quantified6.02 (0.24-68.63) uMAdult (>18 years old)Female
Breast cancer		 details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Zhang Z, Chen H, Chan KK, Budd T, Ganapathi R: Gas chromatographic-mass spectrometric analysis of perillyl alcohol and metabolites in plasma. J Chromatogr B Biomed Sci Appl. 1999 May 14;728(1):85-95. [PubMed:10379660 ]
Schizophrenia
  1. Koike S, Bundo M, Iwamoto K, Suga M, Kuwabara H, Ohashi Y, Shinoda K, Takano Y, Iwashiro N, Satomura Y, Nagai T, Natsubori T, Tada M, Yamasue H, Kasai K: A snapshot of plasma metabolites in first-episode schizophrenia: a capillary electrophoresis time-of-flight mass spectrometry study. Transl Psychiatry. 2014 Apr 8;4:e379. doi: 10.1038/tp.2014.19. [PubMed:24713860 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013215
KNApSAcK IDC00010870
Chemspider ID1218
KEGG Compound IDC11924
BioCyc IDNot Available
BiGG ID2266070
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1256
PDB IDNot Available
ChEBI ID36999
Food Biomarker OntologyNot Available
VMH IDPERACD
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSemmler, F. W.; Zaar, B. Constituents of Ethereal Oils. Constitution of Perillaldehyde, C10H14O. Berichte der Deutschen Chemischen Gesellschaft (1911), 44 52-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ripple GH, Gould MN, Arzoomanian RZ, Alberti D, Feierabend C, Simon K, Binger K, Tutsch KD, Pomplun M, Wahamaki A, Marnocha R, Wilding G, Bailey HH: Phase I clinical and pharmacokinetic study of perillyl alcohol administered four times a day. Clin Cancer Res. 2000 Feb;6(2):390-6. [PubMed:10690515 ]
  2. Hudes GR, Szarka CE, Adams A, Ranganathan S, McCauley RA, Weiner LM, Langer CJ, Litwin S, Yeslow G, Halberr T, Qian M, Gallo JM: Phase I pharmacokinetic trial of perillyl alcohol (NSC 641066) in patients with refractory solid malignancies. Clin Cancer Res. 2000 Aug;6(8):3071-80. [PubMed:10955786 ]

Enzymes

Enzyme Details
1. 4-trimethylaminobutyraldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Enzyme Details
2. Alpha-aminoadipic semialdehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Enzyme Details
3. Aldehyde dehydrogenase family 1 member A3
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Enzyme Details
4. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Perillyl aldehyde + Water + NAD → Perillic acid + NADH + Hydrogen Iondetails
Enzyme Details
5. Fatty aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
Perillyl aldehyde + Water + NAD → Perillic acid + NADH + Hydrogen Iondetails
Enzyme Details
6. Aldehyde dehydrogenase X, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
Perillyl aldehyde + Water + NAD → Perillic acid + NADH + Hydrogen Iondetails