Cannabis Compound Database: Showing Compound Card for Phenol (CDB000660)

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Record Information

Version

1.0

Created at

2020-03-19 00:49:35 UTC

Updated at

2020-12-07 19:07:37 UTC

CannabisDB ID

CDB000660

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Phenol

Description

Phenol, also known as hydroxybenzene or carbolic acid, belongs to the class of organic compounds known as hydroxy benzenoids. Phenol is a toxic, colourless crystalline solid with a sweet tarry odor that resembles a hospital smell. It is commonly used as an antiseptic and disinfectant. It is active against a wide range of microorganisms including some fungi and viruses but is only slowly effective against spores. It has been used to disinfect skin and to relieve itching. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins. Phenol can be found in areas with high levels of motor traffic, therefore, people living in crowded urban areas are frequently exposed to traffic-derived phenol vapor. The average (mean +/- SD) phenol concentration in urine among normal individuals living in urban areas is 7.4 +/- 2.2 mg/g of creatinine. Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe. In laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. In some bacteria phenol can be directly synthesized from tyrosine via the enzyme tyrosine phenol-lyase [EC:4.1.99.2]. It can be produced by Escherichia and Pseudomonas. Phenol has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Phenol also has been reported as a volatile compound detected in cannabis samples obtained through police seizures (PMID: 26657499 ). Phenol is also a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acide carbolique	ChEBI
Acide phenique	ChEBI
Benzenol	ChEBI
Carbolic acid	ChEBI
Carbolsaeure	ChEBI
Hydroxybenzene	ChEBI
Karbolsaeure	ChEBI
Oxybenzene	ChEBI
Phenic acid	ChEBI
Phenylic acid	ChEBI
Phenylic alcohol	ChEBI
PHOH	ChEBI
Liquefied phenol	Kegg
Phenol for disinfection	Kegg
Phenol, liquefied	Kegg
Paoscle	Kegg
Carbolate	Generator
Phenate	Generator
Phenylate	Generator
Anbesol	HMDB
Benzophenol	HMDB
Campho-phenique cold sore gel	HMDB
Campho-phenique gel	HMDB
Campho-phenique liquid	HMDB
Carbolic acid liquid	HMDB
Carbolic oil	HMDB
Carbolicum acidum	HMDB
Carbolsaure	HMDB
Cepastat lozenges	HMDB
Cuticura pain relieving ointment	HMDB
Fenol	HMDB
Fenolo	HMDB
Fenosmolin	HMDB
Fenosmoline	HMDB
Hydroxy-benzene	HMDB
IPH	HMDB
IZAL	HMDB
Liquid phenol	HMDB
Liquified phenol	HMDB
Monohydroxy benzene	HMDB
Monohydroxybenzene	HMDB
Monophenol	HMDB
Phenic	HMDB
Phenic alcohol	HMDB
Phenol alcohol	HMDB
Phenol homopolymer	HMDB
Phenol liquid	HMDB
Phenol molten	HMDB
Phenol polymer-bound	HMDB
Phenol solution	HMDB
Phenol synthetic	HMDB
Phenolated water	HMDB
Phenolated water for disinfection	HMDB
Phenole	HMDB
Phenosmolin	HMDB
Synthetic phenol	HMDB
Tea polyphenol	HMDB
Phenol, sodium salt	HMDB
Phenolate sodium	HMDB
Carbol	HMDB
Phenolate, sodium	HMDB
Sodium phenolate	HMDB

Chemical Formula

C₆H₆O

Average Molecular Weight

94.11

Monoisotopic Molecular Weight

94.0419

IUPAC Name

phenol

Traditional Name

phenol

CAS Registry Number

108-95-2

SMILES

OC1=CC=CC=C1

InChI Identifier

InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H

InChI Key

ISWSIDIOOBJBQZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-hydroxy-4-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:15882 )
a phenol (PHENOL )

Ontology

Hypotension

Psychiatric disorders:

Confusion

Ear and labyrinth disorders:

Tinnitus

General disorders and administration site conditions:

Pain

Nervous system disorders:

Headache

Gastrointestinal disorders:

Cardiac disorders:

Cardiovascular disease

Disposition

Source:

Environmental:

Tobacco smoke

Biological:

Microbe:

Escherichia:

Escherichia coli

Pseudomonas:

Pseudomonas putida

Ingestion

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Food and nutrition

Household products:

Antimicrobial agent:

Disinfectant

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	40.9 °C	Not Available
Boiling Point	181.7 °C	Wikipedia
Water Solubility	82.8 mg/mL at 25 °C	Not Available
logP	1.46	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.39	ALOGPS
logP	1.67	ChemAxon
logS	-0.31	ALOGPS
pKa (Strongest Acidic)	10.02	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	28.04 m³·mol⁻¹	ChemAxon
Polarizability	9.81 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

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00kf-9000000000-40b376f4e58c23369a01	2014-09-20	View Spectrum
GC-MS	Phenol, 1 TMS, GC-MS Spectrum	splash10-0udi-3900000000-97dfa3be718a9ee7ace4	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-00kf-9000000000-6fb456992902a13931f9	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-78c83ab6ff1d3dfdbec6	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-89b0c430b8924ee2afde	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-fc01d0ad6740cfd70e13	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-006w-9000000000-c8b41f2899ca8cc9d4bc	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-db80d8b605e20595c679	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-0udi-3900000000-97dfa3be718a9ee7ace4	Spectrum
Predicted GC-MS	Phenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-c35c89484e2499c62a49	Spectrum
Predicted GC-MS	Phenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0g4i-9300000000-afd565a878ea36c74def	Spectrum
Predicted GC-MS	Phenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0006-9000000000-e67da0571423f0e6b4b8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-9000000000-e0f57b1e970d0d46597e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9000000000-e67da0571423f0e6b4b8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-00kf-9000000000-7bfe3b897e928a8f3a2c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-0006-9000000000-78c83ab6ff1d3dfdbec6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0006-9000000000-89b0c430b8924ee2afde	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0006-9000000000-fc01d0ad6740cfd70e13	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-ca4fa5905cccbfeab33a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-e3e33defb000b450bb37	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9200000000-d63db79771e5931b258f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-448a4d79ff53d77a8b16	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-2c7201e803e029dd1aef	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-3fb3990dfbfbde2b8d57	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gba-9000000000-d3da8db6579f32d02c6c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-a74494cda18ab9fb8055	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-a74494cda18ab9fb8055	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-03a61ff7da92cb08edf8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-c65d4a4eaa8adde2ddb4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-9000000000-def7a8d52afb63a3cd67	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-f3c795ffc788635ddbf4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-08485aaf085c13d5129a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-08485aaf085c13d5129a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-52b0f93832ef13f17bd2	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Sulfate/Sulfite Metabolism
Sulfite oxidase deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Serum paraoxonase/lactonase 3	PON3	7q21.3	Q15166	details
Serum paraoxonase/arylesterase 1	PON1	7q21.3	P27169	details
Serum paraoxonase/arylesterase 2	PON2	7q21.3	Q15165	details
6-phosphogluconolactonase	PGLS	19p13.2	O95336	details
Glucose-6-phosphate 1-dehydrogenase	G6PD	Xq28	P11413	details
Sulfotransferase 1A1	SULT1A1	16p12.1	P50225	details
Sulfotransferase 1A2	SULT1A2	16p12.1	P50226	details
Sulfotransferase 1A3/1A4	SULT1A3	16p11.2	P50224	details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
6-phosphogluconate dehydrogenase, decarboxylating	PGD	1p36.22	P52209	details
Putative uncharacterized protein PGD	PGD	1p36.3-p36.13	A9Z1X1	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Serum paraoxonase/arylesterase 1	PON1	7q21.3	P27169	details
Solute carrier family 13 member 4	SLC13A4	7q33	Q9UKG4	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Serum paraoxonase/lactonase 3	PON3	7q21.3	Q15166	details
Serum paraoxonase/arylesterase 2	PON2	7q21.3	Q15165	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000228

DrugBank ID

DB03255

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000893

KNApSAcK ID

C00002664

Chemspider ID

Not Available

KEGG Compound ID

C15584

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenol

METLIN ID

Not Available

PubChem Compound

996

PDB ID

Not Available

ChEBI ID

15882

References

General References

Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Only showing the first 10 proteins. There are 15 proteins in total.

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Enzymes

Enzyme Details

1. Serum paraoxonase/lactonase 3

General function:: Involved in arylesterase activity
Specific function:: Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:: PON3
Uniprot ID:: Q15166
Molecular weight:: 39607.185

Enzyme Details

2. Serum paraoxonase/arylesterase 1

General function:: Involved in arylesterase activity
Specific function:: Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:: PON1
Uniprot ID:: P27169
Molecular weight:: 39730.99

Enzyme Details

3. Serum paraoxonase/arylesterase 2

General function:: Involved in arylesterase activity
Specific function:: Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:: PON2
Uniprot ID:: Q15165
Molecular weight:: 39380.535

Enzyme Details

4. 6-phosphogluconolactonase

General function:: Involved in 6-phosphogluconolactonase activity
Specific function:: Hydrolysis of 6-phosphogluconolactone to 6-phosphogluconate.
Gene Name:: PGLS
Uniprot ID:: O95336
Molecular weight:: 27546.495

Enzyme Details

5. Glucose-6-phosphate 1-dehydrogenase

General function:: Involved in glucose-6-phosphate dehydrogenase activity
Specific function:: Produces pentose sugars for nucleic acid synthesis and main producer of NADPH reducing power.
Gene Name:: G6PD
Uniprot ID:: P11413
Molecular weight:: 62467.88

Enzyme Details

6. Sulfotransferase 1A1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
Gene Name:: SULT1A1
Uniprot ID:: P50225
Molecular weight:: 34165.13

Enzyme Details

7. Sulfotransferase 1A2

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Is also responsible for the sulfonation and activation of minoxidil. Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
Gene Name:: SULT1A2
Uniprot ID:: P50226
Molecular weight:: 34310.43

Enzyme Details

8. Sulfotransferase 1A3/1A4

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P50224
Molecular weight:: 34195.96

Enzyme Details

9. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Enzyme Details

10. 6-phosphogluconate dehydrogenase, decarboxylating

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH (By similarity).
Gene Name:: PGD
Uniprot ID:: P52209
Molecular weight:: 53139.56

Transporters

Enzyme Details

1. Serum paraoxonase/arylesterase 1

General function:: Involved in arylesterase activity
Specific function:: Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:: PON1
Uniprot ID:: P27169
Molecular weight:: 39730.99

Enzyme Details

2. Solute carrier family 13 member 4

General function:: Involved in transporter activity
Specific function:: Sodium/sulfate cotransporter that mediates sulfate reabsorption in the high endothelial venules (HEV)
Gene Name:: SLC13A4
Uniprot ID:: Q9UKG4
Molecular weight:: 69357.9

Only showing the first 10 proteins. There are 15 proteins in total.

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Showing Compound Card for Phenol (CDB000660)

Structure for CDB000660 (Phenol)

Enzymes

Transporters