MiMeDB: Showing metabocard for 2-mMethyl-phenol (MMDBc0001073)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 18:42:39 UTC

Update Date

2024-09-27 23:15:44 UTC

Metabolite ID

MMDBc0001073

Metabolite Identification

Common Name

2-mMethyl-phenol

Description

2-Methyl-phenol, also known as o-Cresol, is a minor urinary metabolite of toluene. 2-methyl-phenol 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 ). 2-Methyl-phenol is used commercially as a disinfectant. Exposure may occur by inhalation, by cutaneous adsorption or by oral ingestion. 2-Methyl-phenol denature and precipitate cellular proteins and thus may rapidly cause poisoning. 2-Methyl-phenol is metabolized by conjugation and oxidation. Ingestion of 2-methyl-phenol 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 ). 2-Methyl-phenol is a microbial metabolite that can be found in Pseudomonas. Besides, 2-methyl-phenol 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, 2-methyl-phenol 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

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

Synonyms

Value	Source
1-Hydroxy-2-methylbenzene	ChEBI
2-Cresol	ChEBI
2-Hydroxy-1-methylbenzene	ChEBI
2-Hydroxytoluene	ChEBI
O-Cresylic acid	ChEBI
O-Kresol	ChEBI
O-Methylphenol	ChEBI
Ortho-cresol	ChEBI
Orthocresol	ChEBI
O-Cresylate	Generator
1-Methyl-2-hydroxybenzene	HMDB
2-Methylphenol	HMDB, MeSH
O-Hydroxytoluene	HMDB
O-Methylphenylol	HMDB
O-Oxytoluene	HMDB
O-Toluol	HMDB
2-Cresol, potassium salt	MeSH, HMDB
2-Cresol, ammonium salt	MeSH, HMDB
2-Cresol, sodium salt	MeSH, HMDB

Molecular Formula

C₇H₈O

Average Mass

108.1378

Monoisotopic Mass

108.057514878

IUPAC Name

2-methylphenol

Traditional Name

o-cresol

CAS Registry Number

Not Available

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

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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

cresol (CHEBI:28054 )
a methylphenol (CPD-109 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	27.5 g/L	ALOGPS
logP	1.89	ALOGPS
logP	2.18	ChemAxon
logS	-0.59	ALOGPS
pKa (Strongest Acidic)	10.37	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	11.83 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)	splash10-0a6r-9600000000-5a01d451557a1b35332a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pbi-9200000000-be9e6e56af8374e66beb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-7900000000-c8eb63e9fe9da99fda0f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ko-5900000000-cef3087dea0c431cce4b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-9600000000-5a01d451557a1b35332a	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pbi-9200000000-be9e6e56af8374e66beb	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-7900000000-c8eb63e9fe9da99fda0f	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ko-5900000000-cef3087dea0c431cce4b	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6900000000-7ba7c816e0edce6b772f	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-06di-7900000000-db9d20fae81c588496fe	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-5900000000-c7d0037b6de77737b7e4	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-151af99851311002a3fa	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03y3-9000000000-260e2bcf6f7dca1a3c9c	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0a6r-9600000000-ac87a40c538d227b6915	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0pbi-9200000000-be9e6e56af8374e66beb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4i-7900000000-1a7cfac9452c2b14f977	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-5d6424b7db2e7e40d6d7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2900000000-e468ad1b8f28b32d7276	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-9000000000-2629c90f57b18d57c59d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-8feea1e7288d5bc80ea5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-22006f43be347c915292	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-9300000000-d3ec19098100f79d4ebd	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0i03-9100000000-267c04454ade05650a34	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-2900000000-c580eec1345db0ab9045	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002f-9000000000-923877cbbb5c2a1edb9c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016u-9000000000-09eba92f6442b1a88ad5	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9800000000-c390212681445a7e2727	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, 90 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
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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	15040915

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	1
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Metabolic reconstruction; Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Food			FooDB	31437929
Plant		Sinapis alba	FooDB	31437929
Plant	Plant	Prunus cerasus	FooDB	31437929
Plant	Plant	Artemisia dracunculus	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Leaves	Mentha x piperita	FooDB	31437929
Plant	Fruit	Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Shoot	Asparagus officinalis	FooDB	31437929
Plant	Leaves	Camellia sinensis	FooDB	31437929
Plant	Seed	Coffea arabica	FooDB	31437929
Plant	Fruit	Capsicum annuum	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	17.5	9.24	32.6	uM	Adult (>18 years old)	Both	Cresol poisoning	HMDB	15040915
Human Feces	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	21494609
Human Urine	Detected but not Quantified					NULL	NULL	Normal	HMDB	21543078
Human Feces	Detected but not Quantified					Children (1-13 years old)	Not Specified	Treated celiac disease	HMDB	21970810
Human Feces	Detected but not Quantified					Children (1-13 years old)	Not Specified	Normal	HMDB	21970810
Human Blood	Detected and Quantified	17.5	9.24	32.6	uM	Adult (>18 years old)	Both	Cresol poisoning	HMDB	15040915
Human Urine	Detected but not Quantified					NULL	NULL	Normal	HMDB	21543078
Human Feces	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	21494609
Human Feces	Detected but not Quantified					Children (1-13 years old)	Not Specified	Normal	HMDB	21970810

External Links

HMDB ID

HMDB0002055

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

O-Cresol

METLIN ID

Not Available

PubChem Compound

335

PDB ID

Not Available

ChEBI ID

28054

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/j.forsciint.2003.10.023. [PubMed:15040915 ]
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. doi: 10.1016/j.jchromb.2004.12.029. [PubMed:15687000 ]

Showing metabocard for 2-mMethyl-phenol (MMDBc0001073)

MOL for #<Metabolite:0x00007f46a88f4f80>

3D MOL for #<Metabolite:0x00007f46a88f4f80>

3D SDF for #<Metabolite:0x00007f46a88f4f80>

3D-SDF for #<Metabolite:0x00007f46a88f4f80>

PDB for #<Metabolite:0x00007f46a88f4f80>

3D PDB for #<Metabolite:0x00007f46a88f4f80>

SMILES for #<Metabolite:0x00007f46a88f4f80>

INCHI for #<Metabolite:0x00007f46a88f4f80>

Structure for #<Metabolite:0x00007f46a88f4f80>

3D Structure for #<Metabolite:0x00007f46a88f4f80>