Showing NP-Card for Perillic acid (NP0000428)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Show more...Show more...
Record Information
Version2.0
Created at2006-08-13 21:42:07 UTC
Updated at2024-09-17 15:41:53 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
Thumb
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
Download

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
Download

SMILES for NP0000428 (Perillic acid)

CC(=C)C1CCC(=CC1)C(O)=O
Download

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)
Download
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
Chemical Shift Submissions
Not Available
Species
Species of Origin
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 ]