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Showing NP-Card for Perillic acid (NP0000428)

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Record Information
Version1.0
Created at2006-08-13 21:42:07 UTC
Updated at2021-08-19 23:58:06 UTC
NP-MRD IDNP0000428
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000428 (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
Download

3D MOL for NP0000428 (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
Download

3D SDF for NP0000428 (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>
NP0000428

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000428 (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
Download

PDB for NP0000428 (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 NP0000428 (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 NP0000428 (Perillic acid)

CC(=C)C1CCC(=CC1)C(O)=O
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INCHI for NP0000428 (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 NMR Assignments
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 Mass166.2200 Da
Monoisotopic Mass166.09938 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Homo sapiensLOTUS Database
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Perilla frutescensLOTUS Database
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia dorisianaKNApSAcK Database
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Spodoptera lituraLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point60 °CNot Available
Boiling Point284.90 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility136.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.428Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.63 g/LALOGPS
logP2.47ALOGPS
logP2.41ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.2 m³·mol⁻¹ChemAxon
Polarizability18.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004586
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1449821
References
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 ]
  3. Nehra G, Andrews S, Rettig J, Gould MN, Haag JD, Howard SP, Thorne RG: Intranasal administration of the chemotherapeutic perillyl alcohol results in selective delivery to the cerebrospinal fluid in rats. Sci Rep. 2021 Mar 18;11(1):6351. doi: 10.1038/s41598-021-85293-4. [PubMed:33737566 ]
  4. Cho HY, Swenson S, Thein TZ, Wang W, Wijeratne NR, Marin-Ramos NI, Katz JE, Hofman FM, Schonthal AH, Chen TC: Pharmacokinetic properties of the temozolomide perillyl alcohol conjugate (NEO212) in mice. Neurooncol Adv. 2020 Nov 20;2(1):vdaa160. doi: 10.1093/noajnl/vdaa160. eCollection 2020 Jan-Dec. [PubMed:33392507 ]
  5. Ravera M, Gabano E, Zanellato I, Rangone B, Perin E, Ferrari B, Bottone MG, Osella D: Cis,cis,trans-[Pt(IV)Cl2(NH3)2(perillato)2], a dual-action prodrug with excellent cytotoxic and antimetastatic activity. Dalton Trans. 2021 Mar 7;50(9):3161-3177. doi: 10.1039/d0dt04051g. Epub 2021 Feb 17. [PubMed:33595015 ]