MiMeDB: Showing metabocard for Resorcinol (MMDBc0054654)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:22:46 UTC

Update Date

2024-04-30 20:55:08 UTC

Metabolite ID

MMDBc0054654

Metabolite Identification

Common Name

Resorcinol

Description

Resorcinol, also known as 1,3-benzenediol, resorcin or m-hydroquinone, belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. Resorcinol exists in all living organisms, ranging from bacteria to humans. Resorcinol is a creamy, hawthorn, and musty tasting compound. Resorcinol has been detected, but not quantified, in several different foods, such as alcoholic beverages, cereals and cereal products, coffee and coffee products, eggplants, and java plums. This could make resorcinol a potential biomarker for the consumption of these foods. Resorcinol is a potentially toxic compound. In addition, exogenous ochronosis is associated with prolonged exposure to resorcinol . Data regarding the specific mechanisms of action of resorcinol does not appear to be readily accessible in the literature. Nevertheless, the role played by iodide ions in the irreversible inactivation of the enzymes is not yet fully elucidated . Resorcinol works by helping to remove hard, scaly, or roughened skin. In particular, it appears that resorcinol indicated for treating acne, dermatitis, or eczema in various skin care topical applications and peels revolves around the compound's ability to precipitate cutaneous proteins from the treated skin . In LPO and TPO, the resulting π-cation radical of the porphyrin can isomerize to a radical cation with the radical in an aromatic side chain of the enzyme . In vitro and in vivo studies have demonstrated that resorcinol can inhibit peroxidases in the thyroid and subsequently block the synthesis of thyroid hormones and cause goiter.

Structure

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

Synonyms

Value	Source
1,3-Dihydroxybenzene	ChEBI
1,3-Dihydroxybenzol	ChEBI
m-Hydroquinone	ChEBI
m-Hydroxyphenol	ChEBI
Resorcin	ChEBI
Resorzin	ChEBI
Resorcinol disodium salt	MeSH
Resorcinol, monocopper (2+) salt	MeSH
1,3-Benzenediol	ChEBI
1,3-Dihydroxy-benzene	HMDB
3-Hydroxyphenol	HMDB
FEMA 3589	HMDB
m-Benzenediol	HMDB
m-Dihydroxybenzene	HMDB
m-Dioxybenzene	HMDB
m-Hydroxy-phenol	HMDB
Resorcinol, 8ci	HMDB
Rezorsine	HMDB
Benzene-1,3-Diol	HMDB
Resorcinol	HMDB

Molecular Formula

C₆H₆O₂

Average Mass

110.1106

Monoisotopic Mass

110.036779436

IUPAC Name

benzene-1,3-diol

Traditional Name

resorcinol

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H

InChI Key

GHMLBKRAJCXXBS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Resorcinol
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

resorcinols (CHEBI:27810 )
benzenediol (CHEBI:27810 )
a benzenediol (CPD-623 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	82.3 g/L	ALOGPS
logP	0.7	ALOGPS
logP	1.37	ChemAxon
logS	-0.13	ALOGPS
pKa (Strongest Acidic)	9.26	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.02 m³·mol⁻¹	ChemAxon
Polarizability	10.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-08gi-9600000000-0e7d24e90c380c2fbaf5	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9500000000-02f0a9b7ce8b4af47473	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03e9-9300000000-fcd22d3e2208eda085dd	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f83-3960000000-6169d32b43f71f4abe1a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-08gi-9600000000-0e7d24e90c380c2fbaf5	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9500000000-02f0a9b7ce8b4af47473	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03e9-9300000000-fcd22d3e2208eda085dd	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f83-3960000000-6169d32b43f71f4abe1a	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-3900000000-523ce2d2022aff1e8307	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00ei-7940000000-20d1bf1b6588a896d381	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-64036e30d95c257972de	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-e75dbf262b9b2cf88b20	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aou-9300000000-6fec697f0a62d05e0740	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1900000000-390a7eb266152d83c925	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-6900000000-ad5c8e451745f725a898	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-8b485ce5f0cbe4811afb	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-920e234b400dba4e5f87	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-b7e895b1f7ab851eecff	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03xu-9300000000-91340faf902dd2ba7d1f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-fd10fd64675560620b8d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03xr-9600000000-b1d387d2d4ab01180df9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-596a7612f830d3e5368f	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-8900000000-3771649f063971fd96f3	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)		2014-09-23	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

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

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
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0016407	Hydrogen Ion	benzene-1,2,4-triol	NADPH-dependent resorcinol 4-hydroxylase	Hydroxylation	RHEA	34755880
MMDBr0016408	Hydrogen Ion	benzene-1,2,4-triol	NADPH-dependent resorcinol 4-hydroxylase	Hydroxylation	RHEA	34755880
MMDBr0016452	2,6-Dihydroxybenzoic acid	Carbon dioxide	Gamma-resorcylate decarboxylase	Decarboxylation	RHEA	34755880
MMDBr0016453	2,6-Dihydroxybenzoic acid	Carbon dioxide	Gamma-resorcylate decarboxylase	Decarboxylation	RHEA	34755880
MMDBr0016479	Hydrogen Ion	benzene-1,2,4-triol	Probable NADH-specific resorcinol 4-hydroxylase	Hydroxylation	RHEA	34755880
MMDBr0016480	Hydrogen Ion	benzene-1,2,4-triol	Probable NADH-specific resorcinol 4-hydroxylase	Hydroxylation	RHEA	34755880
MMDBr0016505	FADH2	benzene-1,2,4-triol	FADH(2)-dependent resorcinol hydroxylase, oxygenase component	Hydroxylation	RHEA	34755880
MMDBr0016506	FADH2	benzene-1,2,4-triol	FADH(2)-dependent resorcinol hydroxylase, oxygenase component	Hydroxylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	2
Bacteria	Proteobacteria	3	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0032037

DrugBank ID

DB11085

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Resorcinol

METLIN ID

Not Available

PubChem Compound

5054

PDB ID

RCO

ChEBI ID

27810

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Resorcinol (MMDBc0054654)

MOL for #<Metabolite:0x00007fd0c5e06788>

3D MOL for #<Metabolite:0x00007fd0c5e06788>

3D SDF for #<Metabolite:0x00007fd0c5e06788>

3D-SDF for #<Metabolite:0x00007fd0c5e06788>

PDB for #<Metabolite:0x00007fd0c5e06788>

3D PDB for #<Metabolite:0x00007fd0c5e06788>

SMILES for #<Metabolite:0x00007fd0c5e06788>

INCHI for #<Metabolite:0x00007fd0c5e06788>

Structure for #<Metabolite:0x00007fd0c5e06788>

3D Structure for #<Metabolite:0x00007fd0c5e06788>