MiMeDB: Showing metabocard for m-Cresol (MMDBc0033668)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:58:11 UTC

Update Date

2024-04-30 20:14:51 UTC

Metabolite ID

MMDBc0033668

Metabolite Identification

Common Name

m-Cresol

Description

m-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
1-Hydroxy-3-methylbenzene	ChEBI
3-Cresol	ChEBI
3-Hydroxytoluene	ChEBI
3-Methylphenol	ChEBI
m-Kresol	ChEBI
m-Methylphenol	ChEBI
Meta-cresol	ChEBI
Metacresol	ChEBI
3-Cresol, calcium salt(1:2)	MeSH
3-Cresol, sodium salt	MeSH
3-Phenylphenol	ChEBI, HMDB
m-Cresylic acid	HMDB
m-Hydroxytoluene	HMDB
m-Oxytoluene	HMDB
m-Toluol	HMDB
m-Cresol	KEGG

Molecular Formula

C₇H₈O

Average Mass

108.1378

Monoisotopic Mass

108.057514878

IUPAC Name

3-methylphenol

Traditional Name

M-cresol

CAS Registry Number

108-39-4

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

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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

cresol (CHEBI:17231 )
a methylphenol (CPD-112 )

Functional Ontology

Not Available

Physical Properties

State

Liquid

Predicted Properties

Property	Value	Source
Water Solubility	25.1 g/L	ALOGPS
logP	1.93	ALOGPS
logP	2.18	ChemAxon
logS	-0.63	ALOGPS
pKa (Strongest Acidic)	10.13	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.08 m³·mol⁻¹	ChemAxon
Polarizability	11.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-f2082b2d78602454887c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9700000000-987a7fd82a03c828f2f6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-5900000000-80356192ec6d2f2cce17	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014l-3900000000-5be628cfaed43892ecb6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-f2082b2d78602454887c	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9700000000-987a7fd82a03c828f2f6	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-5900000000-80356192ec6d2f2cce17	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014l-3900000000-5be628cfaed43892ecb6	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6900000000-b8ad5789d64b1436f653	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01b9-7900000000-bea1778da40d4c1353e5	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-4900000000-ff165ee98ef540125c4f	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kf-9000000000-606fcb6bc90a29dd8728	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-dcdf60701ebd4f253aff	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0a4i-6900000000-8a57217dc9acf65664ce	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0a4i-9700000000-987a7fd82a03c828f2f6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4i-5900000000-80356192ec6d2f2cce17	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-50eeee8ccda679df8336	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-8d97f02d4ffa2f7ea5d7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9100000000-5118914f1ab03a16ca6e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-a61d3231658626b2b393	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-373e69629866322cc176	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9700000000-c3be74dad978cee7d152	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-4900000000-058b7146c5399581303c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-1ab6752f7f0666600263	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-3900000000-1564c33b741bc83530e8	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-054o-9200000000-627147be2fad4471903e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014u-9000000000-4f6fdf895856dea20b9e	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9800000000-f9433af649d30cc0e317	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces
Saliva
Urine

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0014292	6-methylsalicylate	m-Cresol	6-methylsalicylic acid decarboxylase acuB	Decarboxylation	RHEA	34755880
MMDBr0014293	6-methylsalicylate	m-Cresol	6-methylsalicylic acid decarboxylase acuB	Decarboxylation	RHEA	34755880
MMDBr0017182	m-Cresol	3-hydroxybenzyl alcohol	Cytochrome P450 monooxygenase acuC	Oxygenation	RHEA	34755880
MMDBr0017183	m-Cresol	3-hydroxybenzyl alcohol	Cytochrome P450 monooxygenase acuC	Oxygenation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Cresol poisoning ibs		Association	Human Blood	HMDB	11955837

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	7	Human feces; Human saliva; Human supragingival plaque	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Plant	Leaves	Camellia sinensis	FooDB	31437929
Plant	Fruit	Solanum melongena	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Shoot	Asparagus officinalis	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Seed	Coffea arabica	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	2219	2126	2496	uM	Adult (>18 years old)	Both	Cresol poisoning	HMDB	11955837
Human Blood	Detected and Quantified	8849	8877	9062	uM	Adult (>18 years old)	Both	Cresol poisoning	HMDB	11955837
Human Urine	Detected and Quantified	0.13			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Feces	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	21494609
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	HMDB	23454028
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	23454028
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24029555
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	Zerihun T. Dame, Farid Aziat, Rupasri Mandal, Ram Krishnamurthy, Souhaila Bouatra, Shima Borzouie, An Chi Guo, Tanvir Sajed, Lu Deng, Hong Lin, Philip Liu, Edison Dong, David S. Wishart "The human saliva metabolome" Metabolomics (2015) DOI 10.1007/s11306-015-0840-5
Human Blood	Detected and Quantified	2219.0	2126.0	2496.0	uM	Adult (>18 years old)	Both	Cresol poisoning	HMDB	11955837
Human Blood	Detected and Quantified	8849.0	8877.0	9062.0	uM	Adult (>18 years old)	Both	Cresol poisoning	HMDB	11955837
Human Urine	Detected and Quantified	0.13			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Feces	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	21494609
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	23454028
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24029555

External Links

HMDB ID

HMDB0002048

DrugBank ID

DB01776

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

M-cresol

METLIN ID

Not Available

PubChem Compound

342

PDB ID

Not Available

ChEBI ID

17231

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
Plantin P, Sassolas B, Guillet MH, Tater D, Guillet G: [Cutaneous allergic accidents caused by insulin. Current aspects apropos of 2 cases]. Ann Dermatol Venereol. 1988;115(8):813-7. [PubMed:2974269 ]
McSherry TJ: Incompatibility between chlorpromazine and metacresol. Am J Hosp Pharm. 1987 Jul;44(7):1574. [PubMed:3631086 ]
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 ]
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 ]
Das Gupta V: Quantitation of meperidine hydrochloride in pharmaceutical dosage forms by high-performance liquid chromatography. J Pharm Sci. 1983 Jun;72(6):695-7. doi: 10.1002/jps.2600720625. [PubMed:6875832 ]
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 ]
Jorgensen JT: Improvement of patient convenience in treatment with growth hormone. J Pediatr Endocrinol. 1994 Apr-Jun;7(2):175-80. doi: 10.1515/jpem.1994.7.2.175. [PubMed:8061763 ]
Gloge A, Langer B, Poppe L, Retey J: The behavior of substrate analogues and secondary deuterium isotope effects in the phenylalanine ammonia-lyase reaction. Arch Biochem Biophys. 1998 Nov 1;359(1):1-7. doi: 10.1006/abbi.1998.0860. [PubMed:9799553 ]
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 ]
Hussain K, Campagnolo ER: Suspected cresol poisoning in cattle presented for slaughter. Vet Hum Toxicol. 2002 Feb;44(1):11-4. [PubMed:11824764 ]
Clerx V, Van Den Keybus C, Kochuyt A, Goossens A: Drug intolerance reaction to insulin therapy caused by metacresol. Contact Dermatitis. 2003 Mar;48(3):162-3. doi: 10.1034/j.1600-0536.2003.00034.x. [PubMed:12755733 ]
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. doi: 10.1093/ajhp/60.9.916. [PubMed:12756943 ]
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. doi: 10.1177/095632020501600205. [PubMed:15889535 ]
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. doi: 10.1016/j.transproceed.2005.05.020. [PubMed:16182826 ]
Leonet J, Malaise J, Goffin E, Lefebvre C, Tennstedt D, Vandeleene B, Buysschaert M, Squifflet JP: Solitary pancreas transplantation for life-threatening allergy to human insulin. Transpl Int. 2006 Jun;19(6):474-7. doi: 10.1111/j.1432-2277.2006.00282.x. [PubMed:16771868 ]
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 ]

Showing metabocard for m-Cresol (MMDBc0033668)

MOL for #<Metabolite:0x00007fa4e3097240>

3D MOL for #<Metabolite:0x00007fa4e3097240>

3D SDF for #<Metabolite:0x00007fa4e3097240>

3D-SDF for #<Metabolite:0x00007fa4e3097240>

PDB for #<Metabolite:0x00007fa4e3097240>

3D PDB for #<Metabolite:0x00007fa4e3097240>

SMILES for #<Metabolite:0x00007fa4e3097240>

INCHI for #<Metabolite:0x00007fa4e3097240>

Structure for #<Metabolite:0x00007fa4e3097240>

3D Structure for #<Metabolite:0x00007fa4e3097240>