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Showing NP-Card for (s)-(-)-Perillyl alcohol (NP0002793)

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Record Information
Version1.0
Created at2020-11-23 19:40:35 UTC
Updated at2021-08-19 23:59:23 UTC
NP-MRD IDNP0002793
Secondary Accession NumbersNone
Natural Product Identification
Common Name(s)-(-)-Perillyl alcohol
Provided ByBMRBBMRB logo
Description(S)-(-)-perillyl alcohol, also known as p-mentha-1,8-dien-7-ol, 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. Thus, (S)-(-)-perillyl alcohol is considered to be an isoprenoid. (s)-(-)-Perillyl alcohol is found in Bunium persicum, Canella winterana, Citrus aurantium, Citrus iyo, Citrus sinensis, Laser trilobum, Perilla frutescens, Salvia dorisiana and Teucrium pestalozzae. It was first documented in 2008 (PMID: 17984079). Based on a literature review a small amount of articles have been published on (S)-(-)-perillyl alcohol (PMID: 24125633) (PMID: 24623736) (PMID: 28233648) (PMID: 34362338) (PMID: 34298603) (PMID: 34254911).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002793 ((s)-(-)-Perillyl alcohol)

Perillyl aldehyde metabolite 1
  Mrv1572001071617222D          

 11 11  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
    0.0000   -0.8250    0.0000 C   0  0  1  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    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
  3  7  1  6  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  5  4  1  0  0  0  0
  5  1  2  0  0  0  0
  2 11  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
  9 10  1  0  0  0  0
  1 11  1  0  0  0  0
M  END
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3D MOL for NP0002793 ((s)-(-)-Perillyl alcohol)

NP0002793
     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
   -2.3411   -0.7479   -1.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1578   -0.2893   -0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2689    0.4406    0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8755   -0.4787    0.2945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3101    0.8007    0.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736    1.3160    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8137    0.4466   -0.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320    0.8357   -0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1273    0.4827   -0.1685 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154   -0.9839    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1391   -1.2160   -0.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3084   -0.5822   -2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6015   -1.2951   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2312    1.5357    0.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2531   -0.0033   -0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1410    0.2963    1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0895   -1.1878    1.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0484    0.6116    1.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0889    1.5894    0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9872    2.3798   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212    1.9234   -1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1271    0.3527   -1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2352   -0.4988   -0.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -1.6742   -0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3564   -0.9847    1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -0.7939   -1.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919   -2.2754   -0.5504 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  1  0
  7 10  1  0
 10 11  1  0
 11  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  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
M  END
Download

3D SDF for NP0002793 ((s)-(-)-Perillyl alcohol)

Perillyl aldehyde metabolite 1
  Mrv1572001071617222D          

 11 11  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
    0.0000   -0.8250    0.0000 C   0  0  1  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    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
  3  7  1  6  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  5  4  1  0  0  0  0
  5  1  2  0  0  0  0
  2 11  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
  9 10  1  0  0  0  0
  1 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0002793

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H]1CCC(CO)=CC1

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3/t10-/m1/s1

> <INCHI_KEY>
NDTYTMIUWGWIMO-SNVBAGLBSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.24945808747195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(4S)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
1.9390414949999997

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.85657008950134

> <JCHEM_PKA_STRONGEST_BASIC>
-1.986736242852114

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
48.254999999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-perillyl alcohol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002793 ((s)-(-)-Perillyl alcohol)

NP0002793
     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
   -2.3411   -0.7479   -1.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1578   -0.2893   -0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2689    0.4406    0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8755   -0.4787    0.2945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3101    0.8007    0.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736    1.3160    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8137    0.4466   -0.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320    0.8357   -0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1273    0.4827   -0.1685 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5154   -0.9839    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1391   -1.2160   -0.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3084   -0.5822   -2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6015   -1.2951   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2312    1.5357    0.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2531   -0.0033   -0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1410    0.2963    1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0895   -1.1878    1.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0484    0.6116    1.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0889    1.5894    0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9872    2.3798   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212    1.9234   -1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1271    0.3527   -1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2352   -0.4988   -0.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -1.6742   -0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3564   -0.9847    1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -0.7939   -1.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919   -2.2754   -0.5504 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  1  0
  7 10  1  0
 10 11  1  0
 11  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  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
M  END
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PDB for NP0002793 ((s)-(-)-Perillyl alcohol)

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Perillyl aldehyde metabolite 1                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         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       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   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  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
CONECT    1    9    5   11                                                  
CONECT    2   11    3                                                       
CONECT    3    7    4    2                                                  
CONECT    4    5    3                                                       
CONECT    5    4    1                                                       
CONECT    6    7                                                            
CONECT    7    3    6    8                                                  
CONECT    8    7                                                            
CONECT    9    1   10                                                       
CONECT   10    9                                                            
CONECT   11    2    1                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0002793 ((s)-(-)-Perillyl alcohol)

COMPND    NP0002793
HETATM    1  C1  UNL     1      -2.341  -0.748  -1.652  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.158  -0.289  -0.426  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.269   0.441   0.247  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.876  -0.479   0.294  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.310   0.801   0.816  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.874   1.316   0.089  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.814   0.447  -0.262  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.032   0.836  -0.984  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.127   0.483  -0.168  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.515  -0.984   0.134  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.139  -1.216  -0.533  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.308  -0.582  -2.152  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.602  -1.295  -2.231  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.231   1.536   0.055  1.00  0.00           H  
HETATM   15  H4  UNL     1      -4.253  -0.003  -0.007  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.141   0.296   1.346  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.089  -1.188   1.168  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.048   0.612   1.872  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.089   1.589   0.951  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.987   2.380  -0.161  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.021   1.923  -1.143  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.127   0.353  -1.981  1.00  0.00           H  
HETATM   23  H12 UNL     1       4.235  -0.499  -0.162  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.267  -1.674  -0.243  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.356  -0.985   1.216  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.215  -0.794  -1.574  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.092  -2.275  -0.550  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   11   17
CONECT    5    6   18   19
CONECT    6    7    7   20
CONECT    7    8   10
CONECT    8    9   21   22
CONECT    9   23
CONECT   10   11   24   25
CONECT   11   26   27
END
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SMILES for NP0002793 ((s)-(-)-Perillyl alcohol)

CC(=C)[C@H]1CCC(CO)=CC1
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INCHI for NP0002793 ((s)-(-)-Perillyl alcohol)

InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3/t10-/m1/s1
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View in JSmol
Synonyms
ValueSource
(-)-PerillylalcoholChEBI
(4S)-Perillyl alcoholChEBI
4-Isopropenylcyclohex-1-en-1-ylmethanolChEBI
p-Mentha-1,8-dien-7-olChEBI
Perillyl alcoholChEBI
(S)-Perillyl alcoholKegg
[(4S)-4-(Prop-1-en-2-yl)cyclohex-1-en-1-yl]methanolKegg
4-Isopropenyl-cyclohex-1-ene-1-methanolMeSH
Cyclohex-1-ene-1-methanol, 4(1-methylethenyl)MeSH
Perilla alcoholMeSH
Perilla alcohol, (R)-isomerMeSH
Perilla alcohol, (S)-isomerMeSH
Dihydrocuminyl alcoholMeSH
(-)-p-Mentha-1,8-dien-7-olMeSH
Chemical FormulaC10H16O
Average Mass152.2370 Da
Monoisotopic Mass152.12012 Da
IUPAC Name[(4S)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol
Traditional Name(-)-perillyl alcohol
CAS Registry NumberNot Available
SMILES
CC(=C)[C@H]1CCC(CO)=CC1
InChI Identifier
InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3/t10-/m1/s1
InChI KeyNDTYTMIUWGWIMO-SNVBAGLBSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Bunium persicumLOTUS Database
Canella winteranaLOTUS Database
Citrus aurantiumLOTUS Database
Citrus iyoLOTUS Database
Citrus sinensisLOTUS Database
Curcuma manggaKNApSAcK Database
Laser trilobumLOTUS Database
Mentha spicataKNApSAcK Database
Perilla frutescensLOTUS Database
Salvia dorisianaLOTUS Database
Teucrium pestalozzaeLOTUS Database
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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point119.00 to 121.00 °C. @ 11.00 mm HgThe Good Scents Company Information System
Water Solubility471 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.170The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP2.5ALOGPS
logP1.94ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)16.86ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.26 m³·mol⁻¹ChemAxon
Polarizability18.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00053669
Chemspider ID327861
KEGG Compound IDC02452
BioCyc IDCPD-261
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID10782
Good Scents IDrw1031131
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. d'Alessio PA, Bisson JF, Bene MC: Anti-stress effects of d-limonene and its metabolite perillyl alcohol. Rejuvenation Res. 2014 Apr;17(2):145-9. doi: 10.1089/rej.2013.1515. Epub 2014 Apr 8. [PubMed:24125633 ]
  3. Chen TC, Cho HY, Wang W, Barath M, Sharma N, Hofman FM, Schonthal AH: A novel temozolomide-perillyl alcohol conjugate exhibits superior activity against breast cancer cells in vitro and intracranial triple-negative tumor growth in vivo. Mol Cancer Ther. 2014 May;13(5):1181-93. doi: 10.1158/1535-7163.MCT-13-0882. Epub 2014 Mar 12. [PubMed:24623736 ]
  4. Tomaz-Morais JF, Braga RM, de Sousa FB, de Sousa DP, deM Pordeus LC, de Almeida RN, de Castro RD: Orofacial antinociceptive activity of (S)-(-)-perillyl alcohol in mice: a randomized, controlled and triple-blind study. Int J Oral Maxillofac Surg. 2017 May;46(5):662-667. doi: 10.1016/j.ijom.2017.01.024. Epub 2017 Feb 21. [PubMed:28233648 ]
  5. Chebet JJ, Ehiri JE, McClelland DJ, Taren D, Hakim IA: Effect of d-limonene and its derivatives on breast cancer in human trials: a scoping review and narrative synthesis. BMC Cancer. 2021 Aug 6;21(1):902. doi: 10.1186/s12885-021-08639-1. [PubMed:34362338 ]
  6. Schonthal AH, Swenson S, Minea RO, Kim HN, Cho H, Mohseni N, Kim YM, Chen TC: Potentially Curative Therapeutic Activity of NEO212, a Perillyl Alcohol-Temozolomide Conjugate, in Preclinical Cytarabine-Resistant Models of Acute Myeloid Leukemia. Cancers (Basel). 2021 Jul 6;13(14). pii: cancers13143385. doi: 10.3390/cancers13143385. [PubMed:34298603 ]
  7. Kutyla M, Maciejczyk A, Trytek M, Jakubowicz-Gil J: Biocatalytic synthesis of terpene esters and their biological activity in human glioma cells. Curr Pharm Biotechnol. 2021 Jul 11. pii: CPB-EPUB-116619. doi: 10.2174/1389201022666210712094925. [PubMed:34254911 ]