MiMeDB: Showing metabocard for Perillic acid (MMDBc0048217)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:54:00 UTC

Update Date

2024-04-30 20:36:00 UTC

Metabolite ID

MMDBc0048217

Metabolite Identification

Common Name

Perillic acid

Description

Perillic 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

MOL SDF PDB SMILES InChI


  Mrv1652304292223542D          

 25 25  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.7605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    3.1895    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525    0.8730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8823    1.5143    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8236   -0.0480    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533   -0.6893    0.0000 H   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
   -0.7752    1.1072    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752    0.5428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  CHG  1  18  -1
M  END
> <DATABASE_ID>
MMDBc0048217

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C([H])=C(C([H])([H])[H])C1([H])C([H])([H])C([H])=C(C([O-])=O)C([H])([H])C1([H])[H]

> <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)/p-1

> <INCHI_KEY>
CDSMSBUVCWHORP-UHFFFAOYSA-M

> <FORMULA>
C10H13O2

> <MOLECULAR_WEIGHT>
165.213

> <EXACT_MASS>
165.092103239

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
18.139617105908464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.411505250666667

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.991443593247135

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
59.0346

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
perillate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  H   UNK     0       0.000   6.160   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0      -1.334   3.850   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       3.437   3.286   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0       4.001   5.390   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0       1.897   5.954   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       4.205   1.630   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       3.514   2.827   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       4.001  -0.770   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O-1
HETATM   19  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      -1.537  -0.090   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.846  -1.287   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      -1.447   2.067   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.447   1.013   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    4   10   11   23                                             
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20    9   24   25                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

Synonyms

Value	Source
4-(1-Methylethenyl)-1-cyclohexene-1-carboxylate	ChEBI
4-Isopropenylcyclohex-1-enecarboxylate	ChEBI
Perillyl carboxylate	ChEBI
4-(1-Methylethenyl)-1-cyclohexene-1-carboxylic acid	Generator
4-Isopropenylcyclohex-1-enecarboxylic acid	Generator
Perillyl carboxylic acid	Generator
Perillic acid	Generator

Molecular Formula

C₁₀H₁₃O₂

Average Mass

165.213

Monoisotopic Mass

165.092103239

IUPAC Name

4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylate

Traditional Name

perillate

CAS Registry Number

7694-45-3

SMILES

[H]C([H])=C(C([H])([H])[H])C1([H])C([H])([H])C([H])=C(C([O-])=O)C([H])([H])C1([H])[H]

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)/p-1

InChI Key

CDSMSBUVCWHORP-UHFFFAOYSA-M

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane 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
Organic anion
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

monocarboxylic acid anion (CHEBI:62641 )
a carboxylate (CPD-12443 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.5 g/L	ALOGPS
logP	2.82	ALOGPS
logP	2.41	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	59.03 m³·mol⁻¹	ChemAxon
Polarizability	18.14 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Mitochondria

Biospecimen Locations

Blood
Feces
Kidney
Liver

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0002043	Perillyl aldehyde	Perillic acid	aldehyde dehydrogenase 1 family, member A1		VMH	30371894
MMDBr0002044	Perillyl aldehyde	Perillic acid	aldehyde dehydrogenase 1 family, member B1		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human Blood	Detected and Quantified	6.02	0.24	68.63	uM	Adult (>18 years old)	Female	Breast cancer	HMDB	10379660
Human Kidney	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24713860

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7822082

KEGG Compound ID

Not Available

BioCyc ID

CPD-12443

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9543109

PDB ID

Not Available

ChEBI ID

62641

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
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 ]

Showing metabocard for Perillic acid (MMDBc0048217)

MOL for #<Metabolite:0x00007fdb4959c348>

3D MOL for #<Metabolite:0x00007fdb4959c348>

3D SDF for #<Metabolite:0x00007fdb4959c348>

3D-SDF for #<Metabolite:0x00007fdb4959c348>

PDB for #<Metabolite:0x00007fdb4959c348>

3D PDB for #<Metabolite:0x00007fdb4959c348>

SMILES for #<Metabolite:0x00007fdb4959c348>

INCHI for #<Metabolite:0x00007fdb4959c348>

Structure for #<Metabolite:0x00007fdb4959c348>

3D Structure for #<Metabolite:0x00007fdb4959c348>