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Showing NP-Card for Pentamethylbenzene (NP0045168)

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Record Information
Version2.0
Created at2022-03-10 18:59:08 UTC
Updated at2022-03-10 22:22:02 UTC
NP-MRD IDNP0045168
Secondary Accession NumbersNone
Natural Product Identification
Common NamePentamethylbenzene
DescriptionPentamethylbenzene or 1,2,3,4,5-pentamethylbenzene, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Pentamethylbenzene is an aromatic hydrocarbon with the formula C6H(CH3)5. Structurally, pentamethylbenzene is a benzene in which five of the hydrogens are replaced by methyl groups. Pentamethylbenzene is a colorless solid under normal temperature and pressure conditions. It has a sweet odour. It is electron rich and is readily oxidized, easily undergoing electrophilic substitutions. Pentamethylbenzene has been observed as an intermediate in the formation of hexamethylbenzene from phenol (https://Doi.Org/10.1021/Jo01037a517) and alkylation of durene or pentamethylbenzene has been reported as a suitable starting material for the synthesis of hexamethylbenzene (DOI: 10.15227/Orgsyn.010.0032). Pentamethylbenzene has been reported as a volatile compound detected in cannabis samples obtained through police seizures (PMID: 26657499 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045168 (Pentamethylbenzene)


  Mrv1652303202018592D          

 11 11  0  0  0  0            999 V2000
    0.7145    2.0625    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    0.8250    0.0000 C   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 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   -1.2375    0.0000 C   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
   -0.7145   -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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0045168 (Pentamethylbenzene)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
   -2.4317   -1.8381   -0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1412   -1.0898   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0714   -1.7473   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653   -1.0382   -0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5709   -1.7326   -0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1857    0.3320    0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4443    1.1188    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0273    1.0178    0.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0767    2.5065    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2040    0.2928   -0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5097    0.9886   -0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -2.8969   -0.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0681   -1.4820   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969   -1.7740    0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0873   -2.8152   -0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9523   -1.9351   -1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3300   -1.2457    0.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4180   -2.7556    0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    1.5502    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151    0.5681   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982    1.9880   -0.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2630    2.9694   -0.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8712    2.8388    0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9057    2.7578    0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6246    1.6612    0.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903    1.5310   -0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3251    0.2295    0.0929 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  1  0
  4  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  5 16  1  0
  5 17  1  0
  5 18  1  0
  7 19  1  0
  7 20  1  0
  7 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
M  END
Download

3D SDF for NP0045168 (Pentamethylbenzene)


  Mrv1652303202018592D          

 11 11  0  0  0  0            999 V2000
    0.7145    2.0625    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    0.8250    0.0000 C   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 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   -1.2375    0.0000 C   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
   -0.7145   -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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045168

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(C)=C(C)C(C)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C11H16/c1-7-6-8(2)10(4)11(5)9(7)3/h6H,1-5H3

> <INCHI_KEY>
BEZDDPMMPIDMGJ-UHFFFAOYSA-N

> <FORMULA>
C11H16

> <MOLECULAR_WEIGHT>
148.249

> <EXACT_MASS>
148.125200515

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.0886286106265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,3,4,5-pentamethylbenzene

> <ALOGPS_LOGP>
4.42

> <JCHEM_LOGP>
4.540352762666666

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
51.264

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentamethylbenzene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0045168 (Pentamethylbenzene)

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PDB for NP0045168 (Pentamethylbenzene)
HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -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  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0045168 (Pentamethylbenzene)
Download
SMILES for NP0045168 (Pentamethylbenzene)
CC1=CC(C)=C(C)C(C)=C1C
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INCHI for NP0045168 (Pentamethylbenzene)
InChI=1S/C11H16/c1-7-6-8(2)10(4)11(5)9(7)3/h6H,1-5H3
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View in JSmol
Synonyms
ValueSource
PentamethylbenzolChEBI
Chemical FormulaC11H16
Average Mass148.2490 Da
Monoisotopic Mass148.12520 Da
IUPAC Name1,2,3,4,5-pentamethylbenzene
Traditional Namepentamethylbenzene
CAS Registry Number700-12-9
SMILES
CC1=CC(C)=C(C)C(C)=C1C
InChI Identifier
InChI=1S/C11H16/c1-7-6-8(2)10(4)11(5)9(7)3/h6H,1-5H3
InChI KeyBEZDDPMMPIDMGJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 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, 1000 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 NMR1H NMR Spectrum (1D, 200 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 NMR13C NMR Spectrum (1D, 101 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, 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 NMR13C NMR Spectrum (1D, 151 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, 176 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, 201 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, 226 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
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cannabis sativaNULL
      Not Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives  
Alternative Parents
Substituents
  • Monocyclic benzene moiety
    • 

  • Aromatic hydrocarbon
    • 

  • Unsaturated hydrocarbon
    • 

  • Hydrocarbon
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.42ALOGPS
logP4.54ChemAxon
logS-3.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51.26 m³·mol⁻¹ChemAxon
Polarizability19.09 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPentamethylbenzene  
METLIN IDNot Available
PubChem Compound12784  
PDB IDNot Available
ChEBI ID38998  
Good Scents IDNot Available
References
General References
  1. Aschmann SM, Arey J, Atkinson R: Rate constants for the reactions of OH radicals with 1,2,4,5-tetramethylbenzene, pentamethylbenzene, 2,4,5-trimethylbenzaldehyde, 2,4,5-trimethylphenol, and 3-methyl-3-hexene-2,5-dione and products of OH + 1,2,4,5-tetramethylbenzene. J Phys Chem A. 2013 Mar 28;117(12):2556-68. doi: 10.1021/jp400323n. Epub 2013 Mar 18. [PubMed:23495920  ] 
  2. Okano K: [Synthetic studies on natural products with aromatic nitrogen heterocycles based on development of the methods for the formation of aryl carbon-nitrogen bond]. Yakugaku Zasshi. 2013;133(10):1065-78. doi: 10.1248/yakushi.13-00189. [PubMed:24088350  ] 
  3. Jung J, Ohkubo K, Prokop-Prigge KA, Neu HM, Goldberg DP, Fukuzumi S: Photochemical oxidation of a manganese(III) complex with oxygen and toluene derivatives to form a manganese(V)-oxo complex. Inorg Chem. 2013 Dec 2;52(23):13594-604. doi: 10.1021/ic402121j. Epub 2013 Nov 12. [PubMed:24219426  ]