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Showing metabocard for p-Cymene (HMDB0005805)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-01-22 23:51:51 UTC
Update Date2022-03-07 02:49:29 UTC
HMDB IDHMDB0005805
Secondary Accession Numbers
  • HMDB05805
Metabolite Identification
Common Namep-Cymene
DescriptionCymene, or p-cymene also known as p-cymol or isopropyltoluene, is a naturally occurring aromatic organic compound. It is classified as a hydrocarbon related to a monoterpene. Its structure consists of a benzene ring para-substituted with a methyl group and an isopropyl group. It is insoluble in water, but miscible with ethanol and ether. Cymene is a constituent of a number of essential oils, most commonly the oil of cumin and thyme. There are two less common geometric isomers. o-Cymene, in which the alkyl groups are ortho-substituted, and m-cymene, in which they are meta-substituted. p-Cymene is the only natural isomer. Cymene is a common ligand for ruthenium.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0005805 (p-Cymene)

  Mrv1652309272007412D          

 10 10  0  0  0  0            999 V2000
   -0.1783    0.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8928    1.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6073    0.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6073   -0.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929   -0.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1783   -0.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5360    1.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5360    1.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2505    0.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3218   -0.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  4 10  1  0  0  0  0
M  END
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3D MOL for HMDB0005805 (p-Cymene)

HMDB0005805
     RDKit          3D
p-Cymene
 24 24  0  0  0  0  0  0  0  0999 V2000
    3.8030    0.0570   -0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3370   -0.0225   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7652   -0.9492    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3802   -1.0392    0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550   -0.1834    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8983   -0.2796    0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5761   -0.6456   -0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5462    1.0212    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1090    0.7470   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940    0.8393   -0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1302    1.1091   -0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2840   -0.6251    0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0546   -0.3175   -1.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4269   -1.6254    1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0523   -1.8077    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1877   -1.0845    1.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1474   -0.0671   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6435   -0.3615   -0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5580   -1.7383   -1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168    1.6147    1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066    1.5940   -0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603    0.7539    1.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757    1.4460   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9353    1.5644   -1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
M  END
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3D SDF for HMDB0005805 (p-Cymene)

  Mrv1652309272007412D          

 10 10  0  0  0  0            999 V2000
   -0.1783    0.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8928    1.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6073    0.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6073   -0.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929   -0.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1783   -0.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5360    1.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5360    1.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2505    0.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3218   -0.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  4 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005805

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=CC=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3

> <INCHI_KEY>
HFPZCAJZSCWRBC-UHFFFAOYSA-N

> <FORMULA>
C10H14

> <MOLECULAR_WEIGHT>
134.222

> <EXACT_MASS>
134.109550451

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.000334634237777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-4-(propan-2-yl)benzene

> <ALOGPS_LOGP>
4.17

> <JCHEM_LOGP>
3.731676356

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
45.29

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cymene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0005805 (p-Cymene)

HMDB0005805
     RDKit          3D
p-Cymene
 24 24  0  0  0  0  0  0  0  0999 V2000
    3.8030    0.0570   -0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3370   -0.0225   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7652   -0.9492    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3802   -1.0392    0.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550   -0.1834    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8983   -0.2796    0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5761   -0.6456   -0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5462    1.0212    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1090    0.7470   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940    0.8393   -0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1302    1.1091   -0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2840   -0.6251    0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0546   -0.3175   -1.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4269   -1.6254    1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0523   -1.8077    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1877   -1.0845    1.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1474   -0.0671   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6435   -0.3615   -0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5580   -1.7383   -1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168    1.6147    1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066    1.5940   -0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603    0.7539    1.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757    1.4460   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9353    1.5644   -1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
M  END
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PDB for HMDB0005805 (p-Cymene)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -0.333   1.312   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.667   2.082   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.000   1.312   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.000  -0.228   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.667  -0.998   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.333  -0.228   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.001   2.082   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.001   3.622   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.334   1.312   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.334  -0.998   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0005805 (p-Cymene)

COMPND    HMDB0005805
HETATM    1  C1  UNL     1       3.803   0.057  -0.237  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.337  -0.022  -0.066  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.765  -0.949   0.764  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.380  -1.039   0.939  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.455  -0.183   0.268  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.898  -0.280   0.452  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.576  -0.646  -0.876  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.546   1.021   0.872  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.109   0.747  -0.564  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.494   0.839  -0.740  1.00  0.00           C  
HETATM   11  H1  UNL     1       4.130   1.109  -0.079  1.00  0.00           H  
HETATM   12  H2  UNL     1       4.284  -0.625   0.504  1.00  0.00           H  
HETATM   13  H3  UNL     1       4.055  -0.317  -1.235  1.00  0.00           H  
HETATM   14  H4  UNL     1       2.427  -1.625   1.294  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.052  -1.808   1.617  1.00  0.00           H  
HETATM   16  H6  UNL     1      -2.188  -1.084   1.158  1.00  0.00           H  
HETATM   17  H7  UNL     1      -2.147  -0.067  -1.706  1.00  0.00           H  
HETATM   18  H8  UNL     1      -3.644  -0.362  -0.783  1.00  0.00           H  
HETATM   19  H9  UNL     1      -2.558  -1.738  -1.047  1.00  0.00           H  
HETATM   20  H10 UNL     1      -1.917   1.615   1.549  1.00  0.00           H  
HETATM   21  H11 UNL     1      -2.907   1.594  -0.015  1.00  0.00           H  
HETATM   22  H12 UNL     1      -3.460   0.754   1.447  1.00  0.00           H  
HETATM   23  H13 UNL     1      -0.476   1.446  -1.119  1.00  0.00           H  
HETATM   24  H14 UNL     1       1.935   1.564  -1.389  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3   10
CONECT    3    4   14
CONECT    4    5    5   15
CONECT    5    6    9
CONECT    6    7    8   16
CONECT    7   17   18   19
CONECT    8   20   21   22
CONECT    9   10   10   23
CONECT   10   24
END
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SMILES for HMDB0005805 (p-Cymene)

CC(C)C1=CC=C(C)C=C1
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INCHI for HMDB0005805 (p-Cymene)

InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H14
Average Molecular Weight134.222
Monoisotopic Molecular Weight134.109550451
IUPAC Name1-methyl-4-(propan-2-yl)benzene
Traditional Namecymene
CAS Registry Number99-87-6
SMILES
CC(C)C1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3
InChI KeyHFPZCAJZSCWRBC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • P-cymene
  • Phenylpropane
  • Cumene
  • Toluene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-68.9 °CNot Available
Boiling Point176.00 to 178.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.023 mg/mL at 25 °CNot Available
LogP4.10HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017358
KNApSAcK IDC00003040
Chemspider ID7183
KEGG Compound IDC06575
BioCyc IDCPD-1001
BiGG IDNot Available
Wikipedia LinkP-cymene
METLIN IDNot Available
PubChem Compound7463
PDB IDNot Available
ChEBI ID28768
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1032712
References
Synthesis ReferenceFevre, Catherine G. Le; Fevre, Raymond J. W. Le; Robertson, Kathleen W. Dipole moments of p-cymene, 2- and 3-halogeno-pcymenes, carvacrol and thymol, p-ethyltoluene, p-tert-butyltoluene, 1,3-dimethyl-5-tert-butylbenzene, tert-butyl-benzene and its p-nitro
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thompson JD, Chalchat JC, Michet A, Linhart YB, Ehlers B: Qualitative and quantitative variation in monoterpene co-occurrence and composition in the essential oil of Thymus vulgaris chemotypes. J Chem Ecol. 2003 Apr;29(4):859-80. [PubMed:12775148 ]
  2. Nishio T, Patel A, Wang Y, Lau PC: Biotransformations catalyzed by cloned p-cymene monooxygenase from Pseudomonas putida F1. Appl Microbiol Biotechnol. 2001 Apr;55(3):321-5. [PubMed:11341314 ]