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Showing NP-Card for o-Cresol (NP0000361)

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Record Information
Version1.0
Created at2006-05-22 14:17:34 UTC
Updated at2021-10-07 20:40:36 UTC
NP-MRD IDNP0000361
Secondary Accession NumbersNone
Natural Product Identification
Common Nameo-Cresol
DescriptionO-Cresol is a minor urinary metabolite of toluene, O-cresol is a cresol that is phenol substituted by a methyl group at position 2. It is a minor urinary metabolite of toluene. It has a role as a human xenobiotic metabolite. It is widely used chemical with neurotoxicological properties (PMID: 15687000 ). O-Cresol is used commercially as a disinfectant. Exposure may occur by inhalation, by cutaneous adsorption or by oral ingestion. O-Cresol denature and precipitate cellular proteins and thus may rapidly cause poisoning. O-Cresol is metabolized by conjugation and oxidation. Ingestion of o-Cresol cause intense burning of mouth and throat, followed by marked abdominal pain and distress. The minimum lethal dose of cresol by mouth is about 2 g (PMID 15040915 ). O-Cresol is a microbial metabolite that can be found in Pseudomonas. Besides, o-Cresol is one of the chemical compounds found in castoreum. This compound is gathered from the beaver's castor glands and found in the white cedar consumed by the beavers. Together with many other compounds, o-cresol is traditionally extracted from coal tar, the volatile materials obtained in the production of coke from coal. A similar source material is petroleum residues. These residue contains a few percent by weight of phenol and isomeric cresols. In addition to the materials derived from these natural sources, about two thirds of the Western world's supply is produced by methylation of phenol using methanol.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000361 (o-Cresol)


  Mrv1652304272018562D          

  8  8  0  0  0  0            999 V2000
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for NP0000361 (o-Cresol)

HMDB0002055
     RDKit          3D
o-Cresol
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.1467   -0.3095   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6829   -0.2667   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115   -1.3845   -0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -1.3348   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822   -0.1203    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    1.0238    0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506    0.9324    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8542    2.0661    0.2537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6565    0.2585    0.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4857   -1.3772   -0.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4269    0.1634   -1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287   -2.3728   -0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -2.2091   -0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -0.0208    0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7598    2.0028    0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3966    2.9486    0.4169 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  2  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  6 15  1  0
  8 16  1  0
M  END
Download

3D SDF for NP0000361 (o-Cresol)


  Mrv1652304272018562D          

  8  8  0  0  0  0            999 V2000
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000361

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3

> <INCHI_KEY>
QWVGKYWNOKOFNN-UHFFFAOYSA-N

> <FORMULA>
C7H8O

> <MOLECULAR_WEIGHT>
108.1378

> <EXACT_MASS>
108.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.831786386924053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylphenol

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
2.1831018836666667

> <ALOGPS_LOGS>
-0.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.37449852812061

> <JCHEM_PKA_STRONGEST_BASIC>
-5.462420484988653

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
33.0801

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.75e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
o-cresol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000361 (o-Cresol)

HMDB0002055
     RDKit          3D
o-Cresol
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.1467   -0.3095   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6829   -0.2667   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115   -1.3845   -0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -1.3348   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822   -0.1203    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    1.0238    0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506    0.9324    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8542    2.0661    0.2537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6565    0.2585    0.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4857   -1.3772   -0.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4269    0.1634   -1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287   -2.3728   -0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -2.2091   -0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -0.0208    0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7598    2.0028    0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3966    2.9486    0.4169 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  2  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  6 15  1  0
  8 16  1  0
M  END
Download

PDB for NP0000361 (o-Cresol)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    1    4    7                                                  
CONECT    7    5    6    8                                                  
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
Download

3D PDB for NP0000361 (o-Cresol)

COMPND    HMDB0002055
HETATM    1  C1  UNL     1      -2.147  -0.309  -0.190  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.683  -0.267  -0.078  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.111  -1.384  -0.186  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.478  -1.335  -0.081  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.082  -0.120   0.142  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.320   1.024   0.256  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.051   0.932   0.144  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.854   2.066   0.254  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.657   0.258   0.605  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.486  -1.377  -0.246  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.427   0.163  -1.175  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.329  -2.373  -0.364  1.00  0.00           H  
HETATM   13  H5  UNL     1       2.103  -2.209  -0.165  1.00  0.00           H  
HETATM   14  H6  UNL     1       3.175  -0.021   0.235  1.00  0.00           H  
HETATM   15  H7  UNL     1       1.760   2.003   0.432  1.00  0.00           H  
HETATM   16  H8  UNL     1      -0.397   2.949   0.417  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    7
CONECT    3    4   12
CONECT    4    5    5   13
CONECT    5    6   14
CONECT    6    7    7   15
CONECT    7    8
CONECT    8   16
END
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SMILES for NP0000361 (o-Cresol)

CC1=CC=CC=C1O
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INCHI for NP0000361 (o-Cresol)

InChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3
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View in JSmol
Synonyms
ValueSource
1-Hydroxy-2-methylbenzeneChEBI
2-CresolChEBI
2-Hydroxy-1-methylbenzeneChEBI
2-HydroxytolueneChEBI
O-Cresylic acidChEBI
O-KresolChEBI
O-MethylphenolChEBI
Ortho-cresolChEBI
OrthocresolChEBI
O-CresylateGenerator
1-Methyl-2-hydroxybenzeneHMDB
2-MethylphenolHMDB
O-HydroxytolueneHMDB
O-MethylphenylolHMDB
O-OxytolueneHMDB
O-ToluolHMDB
2-Cresol, potassium saltHMDB
2-Cresol, ammonium saltHMDB
2-Cresol, sodium saltHMDB
Chemical FormulaC7H8O
Average Mass108.1378 Da
Monoisotopic Mass108.05751 Da
IUPAC Name2-methylphenol
Traditional Nameo-cresol
CAS Registry Number95-48-7
SMILES
CC1=CC=CC=C1O
InChI Identifier
InChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3
InChI KeyQWVGKYWNOKOFNN-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia capillarisLOTUS Database
Artemisia dracunculusFooDB
Artemisia macrocephalaLOTUS Database
Asparagus officinalisFooDB
Aspergillus candidusLOTUS Database
Azadirachta indicaLOTUS Database
Blepharocalyx salicifoliusLOTUS Database
Brassica hirtaKNApSAcK Database
Capsicum annuumFooDB
Cedronella canariensisLOTUS Database
Coffea arabicaLOTUS Database
Coffea arabica L.FooDB
Curio articulatusLOTUS Database
Daphne odoraLOTUS Database
Erigeron philadelphicusLOTUS Database
Glycyrrhiza glabraLOTUS Database
Melia azadirachKNApSAcK Database
Melia azedarachPlant
Mentha x piperitaFooDB
Osmorhiza aristataLOTUS Database
Paeonia lactifloraLOTUS Database
Paeonia suffruticosaLOTUS Database
Pinus sibiricaKNApSAcK Database
Polygala senegaLOTUS Database
Prunus cerasusFooDB
Salvia trijugaLOTUS Database
Scutellaria baicalensisLOTUS Database
Sinapis albaFooDB
Solanum lycopersicum var. lycopersicumFooDB
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassCresols
Direct ParentOrtho cresols
Alternative Parents
Substituents
  • O-cresol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point29.8 °CNot Available
Boiling Point191.00 to 192.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility25.9 mg/mL at 25 °CNot Available
LogP1.95Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility27.5 g/LALOGPS
logP1.89ALOGPS
logP2.18ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)10.37ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.08 m³·mol⁻¹ChemAxon
Polarizability11.83 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002055
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008785
KNApSAcK IDC00030878
Chemspider ID13835772
KEGG Compound IDC01542
BioCyc IDCPD-109
BiGG IDNot Available
Wikipedia LinkO-Cresol
METLIN IDNot Available
PubChem Compound335
PDB IDNot Available
ChEBI ID28054
Good Scents IDrw1007721
References
General References
  1. Boatto G, Nieddu M, Carta A, Pau A, Lorenzoni S, Manconi P, Serra D: Determination of phenol and o-cresol by GC/MS in a fatal poisoning case. Forensic Sci Int. 2004 Jan 28;139(2-3):191-4. [PubMed:15040915 ]
  2. Fustinoni S, Mercadante R, Campo L, Scibetta L, Valla C, Foa V: Determination of urinary ortho- and meta-cresol in humans by headspace SPME gas chromatography/mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Mar 25;817(2):309-17. [PubMed:15687000 ]
  3. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  4. Kolesov DV, Ivanova VO, Sokolinskaya EL, Kost LA, Balaban PM, Lukyanov KA, Nikitin ES, Bogdanov AM: Impacts of OrX and cAMP-insensitive Orco to the insect olfactory heteromer activity. Mol Biol Rep. 2021 May;48(5):4549-4561. doi: 10.1007/s11033-021-06480-0. Epub 2021 Jun 11. [PubMed:34129187 ]
  5. Qu X, Chen C, Lin J, Qiang W, Zhang L, Sun D: Engineered defect-rich TiO2/g-C3N4 heterojunction: A visible light-driven photocatalyst for efficient degradation of phenolic wastewater. Chemosphere. 2021 Jul 26;286(Pt 1):131696. doi: 10.1016/j.chemosphere.2021.131696. [PubMed:34346347 ]
  6. Zhu X, Luo Z, Zhu X: Novel insights into the enrichment of phenols from walnut shell pyrolysis loop: Torrefaction coupled fractional condensation. Waste Manag. 2021 Jul 15;131:462-470. doi: 10.1016/j.wasman.2021.07.007. Epub 2021 Jul 14. [PubMed:34271394 ]
  7. Qian YL, Zhang D, An Y, Zhou Q, Qian MC: Characterization of Aroma-Active Compounds in Northern Highbush Blueberries "Bluecrop" (Vaccinium corymbosum "Bluecrop") and "Elliott" (Vaccinium corymbosum "Elliott") by Gas Chromatography-Olfactometry Dilution Analysis and Odor Activity Value. J Agric Food Chem. 2021 May 26;69(20):5691-5701. doi: 10.1021/acs.jafc.1c01044. Epub 2021 May 11. [PubMed:33973767 ]
  8. Chen L, Sun W, Wei H, Yang X, Sun C, Yu L: Developing Fe/zeolite catalysts for efficient catalytic wet peroxidation of three isomeric cresols. Environ Sci Pollut Res Int. 2021 Aug;28(31):42622-42636. doi: 10.1007/s11356-021-13336-4. Epub 2021 Apr 5. [PubMed:33818723 ]
  9. Api AM, Belsito D, Biserta S, Botelho D, Bruze M, Burton GA Jr, Buschmann J, Cancellieri MA, Dagli ML, Date M, Dekant W, Deodhar C, Fryer AD, Gadhia S, Jones L, Joshi K, Kumar M, Lapczynski A, Lavelle M, Lee I, Liebler DC, Moustakas H, Na M, Penning TM, Ritacco G, Romine J, Sadekar N, Schultz TW, Selechnik D, Siddiqi F, Sipes IG, Sullivan G, Thakkar Y, Tokura Y: RIFM fragrance ingredient safety assessment, o-cresol, CAS Registry Number 95-48-7. Food Chem Toxicol. 2021 Mar;149 Suppl 1:112112. doi: 10.1016/j.fct.2021.112112. Epub 2021 Mar 13. [PubMed:33727179 ]