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Showing NP-Card for m-Cresol (NP0000709)

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Record Information
Version1.0
Created at2006-05-22 14:17:33 UTC
Updated at2021-10-07 20:40:36 UTC
NP-MRD IDNP0000709
Secondary Accession NumbersNone
Natural Product Identification
Common Namem-Cresol
DescriptionM-Cresol is an isomer of p-cresol and o-cresol. Cresols are organic compounds which are methylphenols. They are a widely occurring natural and manufactured group of aromatic organic compounds which are categorized as phenols (sometimes called phenolics). Depending on the temperature, cresols can be solid or liquid because they have melting points not far from room temperature. Like other types of phenols, they are slowly oxidized by long exposure to air and the impurities often give cresols a yellowish to brownish red tint. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "medicine" smell. Cresol solutions are used as household cleaners and disinfectants, perhaps most famously under the trade name Lysol. In the past, cresol solutions have been used as antiseptics in surgery, but they have been largely displaced in this role by less toxic compounds. Lysol was also advertised as a disinfecting vaginal douche in mid-twentieth century America. Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar, and in brown mixtures such as creosote and cresylic acids, which are wood preservatives. Small organisms in soil and water produce cresols when they break down materials in the environment. Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the skin at very high levels, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, mouth, and throat; abdominal pain and vomiting; heart damage; anemia; liver and kidney damage; facial paralysis; coma; and death. Breathing high levels of cresols for a short time results in irritation of the nose and throat. Aside from these effects, very little is known about the effects of breathing cresols, for example, at lower levels over longer times. Ingesting high levels results in kidney problems, mouth and throat burns, abdominal pain, vomiting, and effects on the blood and nervous system. Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, brain, and lungs. M-Cresol is a microbial metabolite that can be found in Lysinibacillus.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000709 (m-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
   -0.8250    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
   -0.8250    1.4290    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  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for NP0000709 (m-Cresol)

HMDB0002048
     RDKit          3D
m-Cresol
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.2933   -0.6372   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8981   -0.1169   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6203    1.2023    0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6742    1.6785    0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7538    0.8645    0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4802   -0.4528   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5595   -1.2860   -0.5379 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1858   -0.9302   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3495   -1.6853    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9567   -0.0466    0.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6818   -0.6762   -1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4569    1.8541    0.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9021    2.7258    0.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678    1.2411    0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648   -1.7646    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315   -1.9705   -0.5339 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  2  0
  8  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
  7 15  1  0
  8 16  1  0
M  END
Download

3D SDF for NP0000709 (m-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
   -0.8250    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
   -0.8250    1.4290    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  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=CC=C1

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

> <INCHI_KEY>
RLSSMJSEOOYNOY-UHFFFAOYSA-N

> <FORMULA>
C7H8O

> <MOLECULAR_WEIGHT>
108.1378

> <EXACT_MASS>
108.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.910825333510092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methylphenol

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
2.1831018836666667

> <ALOGPS_LOGS>
-0.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.134322591215804

> <JCHEM_PKA_STRONGEST_BASIC>
-5.477095511148552

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
33.0801

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
M-cresol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000709 (m-Cresol)

HMDB0002048
     RDKit          3D
m-Cresol
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.2933   -0.6372   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8981   -0.1169   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6203    1.2023    0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6742    1.6785    0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7538    0.8645    0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4802   -0.4528   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5595   -1.2860   -0.5379 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1858   -0.9302   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3495   -1.6853    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9567   -0.0466    0.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6818   -0.6762   -1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4569    1.8541    0.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9021    2.7258    0.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678    1.2411    0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648   -1.7646    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315   -1.9705   -0.5339 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  2  0
  8  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
  7 15  1  0
  8 16  1  0
M  END
Download

PDB for NP0000709 (m-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      -1.540   0.000   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      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.540   2.667   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    6    7                                                       
CONECT    6    1    3    5                                                  
CONECT    7    4    5    8                                                  
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
Download

3D PDB for NP0000709 (m-Cresol)

COMPND    HMDB0002048
HETATM    1  C1  UNL     1      -2.293  -0.637  -0.068  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.898  -0.117  -0.033  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.620   1.202   0.265  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.674   1.678   0.295  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.754   0.865   0.030  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.480  -0.453  -0.268  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.559  -1.286  -0.538  1.00  0.00           O  
HETATM    8  C7  UNL     1       0.186  -0.930  -0.299  1.00  0.00           C  
HETATM    9  H1  UNL     1      -2.349  -1.685   0.319  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.957  -0.047   0.620  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.682  -0.676  -1.099  1.00  0.00           H  
HETATM   12  H4  UNL     1      -1.457   1.854   0.475  1.00  0.00           H  
HETATM   13  H5  UNL     1       0.902   2.726   0.531  1.00  0.00           H  
HETATM   14  H6  UNL     1       2.768   1.241   0.054  1.00  0.00           H  
HETATM   15  H7  UNL     1       2.965  -1.765   0.249  1.00  0.00           H  
HETATM   16  H8  UNL     1      -0.032  -1.970  -0.534  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    8
CONECT    3    4   12
CONECT    4    5    5   13
CONECT    5    6   14
CONECT    6    7    8    8
CONECT    7   15
CONECT    8   16
END
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SMILES for NP0000709 (m-Cresol)

CC1=CC(O)=CC=C1
Download

INCHI for NP0000709 (m-Cresol)

InChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3
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View in JSmol
Synonyms
ValueSource
1-Hydroxy-3-methylbenzeneChEBI
3-CresolChEBI
3-HydroxytolueneChEBI
3-MethylphenolChEBI
m-KresolChEBI
m-MethylphenolChEBI
Meta-cresolChEBI
MetacresolChEBI
3-PhenylphenolHMDB
m-Cresylic acidHMDB
m-HydroxytolueneHMDB
m-OxytolueneHMDB
m-ToluolHMDB
3-Cresol, sodium saltHMDB
3-Cresol, calcium salt(1:2)HMDB
m-CresolKEGG
Chemical FormulaC7H8O
Average Mass108.1378 Da
Monoisotopic Mass108.05751 Da
IUPAC Name3-methylphenol
Traditional NameM-cresol
CAS Registry Number108-39-4
SMILES
CC1=CC=CC(O)=C1
InChI Identifier
InChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3
InChI KeyRLSSMJSEOOYNOY-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
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Artemisia capillarisLOTUS Database
Artemisia dolosaLOTUS Database
Asparagus officinalisFooDB
Azadirachta indicaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Cedronella canariensisLOTUS Database
CervidaeFooDB
Cervus canadensisFooDB
Coffea arabicaKNApSAcK Database
Coffea arabica L.FooDB
ColumbaFooDB
ColumbidaeFooDB
Daphne papyraceaLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Ginkgo bilobaLOTUS Database
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melia azadirachKNApSAcK Database
Melia azedarachPlant
Nicotiana bonariensisKNApSAcK Database
Nicotiana cavicolaKNApSAcK Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Paeonia lactifloraLOTUS Database
Paeonia suffruticosaLOTUS Database
Penicillium solitumLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Pimpinella anisumLOTUS Database
Pinus sibiricaKNApSAcK Database
Pueraria montanaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassCresols
Direct ParentMeta cresols
Alternative Parents
Substituents
  • M-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
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point11.8 °CNot Available
Boiling Point202.00 to 203.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility22.7 mg/mL at 25 °CNot Available
LogP1.96Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility25.1 g/LALOGPS
logP1.93ALOGPS
logP2.18ChemAxon
logS-0.63ALOGPS
pKa (Strongest Acidic)10.13ChemAxon
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
Polarizability11.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002048
DrugBank IDDB01776
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008788
KNApSAcK IDC00035128
Chemspider ID21105871
KEGG Compound IDC01467
BioCyc IDCPD-112
BiGG IDNot Available
Wikipedia LinkM-cresol
METLIN IDNot Available
PubChem Compound342
PDB IDNot Available
ChEBI ID17231
Good Scents IDrw1007701
References
General References
  1. Oxford JS, Lambkin R, Gibb I, Balasingam S, Chan C, Catchpole A: A throat lozenge containing amyl meta cresol and dichlorobenzyl alcohol has a direct virucidal effect on respiratory syncytial virus, influenza A and SARS-CoV. Antivir Chem Chemother. 2005;16(2):129-34. [PubMed:15889535 ]
  2. Koetsawang A, Koetsawang S: The use of a condensation product of metacresol sulfonic acid with methanal in the treatment of cervical erosion. J Med Assoc Thai. 1980 Nov;63(11):608-10. [PubMed:7205102 ]
  3. Malaise J, Leonet J, Goffin E, Lefebvre C, Tennstedt D, Vandeleene B, Buysschaert M, Squifflet JP: Pancreas transplantation for treatment of generalized allergy to human insulin in type 1 diabetes. Transplant Proc. 2005 Jul-Aug;37(6):2839. [PubMed:16182826 ]
  4. Perez de Salazar JL, Diaz Loya FJ, Garcia Mendoza M: [The trichomonacidal, fungicidal and bactericidal effects of metacresol sulfonic acid polymer with methanal in cervico-vaginitis]. Ginecol Obstet Mex. 1983 Feb;51(310):43-8. [PubMed:6681370 ]
  5. Hussain K, Campagnolo ER: Suspected cresol poisoning in cattle presented for slaughter. Vet Hum Toxicol. 2002 Feb;44(1):11-4. [PubMed:11824764 ]
  6. Wang G, Jing F, Su S: [An experimental study of metacresol burn]. Zhonghua Zheng Xing Shao Shang Wai Ke Za Zhi. 1999 Jul;15(4):305-8. [PubMed:11593614 ]
  7. Jorgensen JT: Improvement of patient convenience in treatment with growth hormone. J Pediatr Endocrinol. 1994 Apr-Jun;7(2):175-80. [PubMed:8061763 ]
  8. Rasmussen LH, Zachmann M, Nilsson P: Authentic recombinant human growth hormone. Results of a multicenter clinical trial in patients with growth hormone deficiency. Helv Paediatr Acta. 1989 Jun;43(5-6):443-8. [PubMed:2663792 ]
  9. Wheeler BJ, Taylor BJ: Successful management of allergy to the insulin excipient metacresol in a child with type 1 diabetes: a case report. J Med Case Rep. 2012 Aug 31;6:263. doi: 10.1186/1752-1947-6-263. [PubMed:22937994 ]
  10. Morfin de Madrigal A, Lopez Amado G: [500 cases of cervicitis treated with metacresol sulfonic acid]. Ginecol Obstet Mex. 1972 Jan;31(183):83-9. [PubMed:5007546 ]
  11. Phares KR, Weiser WE, Miller SP, Myers MA, Wade M: Stability and preservative effectiveness of treprostinil sodium after dilution in common intravenous diluents. Am J Health Syst Pharm. 2003 May 1;60(9):916-22. [PubMed:12756943 ]
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