MiMeDB: Showing metabocard for Indoxyl (MMDBc0048025)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-19 21:49:59 UTC

Update Date

2024-04-30 20:35:12 UTC

Metabolite ID

MMDBc0048025

Metabolite Identification

Common Name

Indoxyl

Description

Indoxyl, also known as 1H-indol-3-ol, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. Indoxyl is isomeric with oxindol and is obtained as an oily liquid. Indoxyl exists in all living organisms, ranging from bacteria to humans. Indoxyl is obtained from indican, which is a glycoside. Obermayer's reagent is a dilute solution FeCl3 in hydrochloric acid. The hydrolysis of indican yields β-D-glucose and indoxyl. Indigo dye is a product of the reaction of indoxyl by a mild oxidizing agent such as atmospheric oxygen. In chemistry, indoxyl is a nitrogenous substance with the chemical formula: C8H7NO. Indoxyl can be found in urine and is titrated with Obermayer's reagent.

Structure

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

Synonyms

Value	Source
1H-indol-3-Ol	ChEBI

Molecular Formula

C₈H₇NO

Average Mass

133.1473

Monoisotopic Mass

133.052763851

IUPAC Name

1H-indol-3-ol

Traditional Name

indoxyl

CAS Registry Number

Not Available

SMILES

OC1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C8H7NO/c10-8-5-9-7-4-2-1-3-6(7)8/h1-5,9-10H

InChI Key

PCKPVGOLPKLUHR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

Alternative Parents

Substituents

Hydroxyindole
Indole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyindoles (CHEBI:17840 )
a small molecule (INDOXYL )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.67 g/L	ALOGPS
logP	1.29	ALOGPS
logP	1.77	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	36.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	39.13 m³·mol⁻¹	ChemAxon
Polarizability	13.78 Å³	ChemAxon
Number of Rings	2	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 - GC-MS (2 TMS)	splash10-004i-3980000000-520b4525adaeb185fb13	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-3980000000-520b4525adaeb185fb13	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kai-1900000000-1c5e163741d871a2c138	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fl3-6910000000-0c8f4cb37b60dcecf8ea	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
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0900000000-e2d4dbd9b806b29ce214	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-056r-9500000000-263e6cbbc9fbea4d1fe2	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-601cd8ae4909db7a541a	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-0276e7599b0c044e16ca	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-003r-8900000000-1a948ecd165e51423035	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-6900000000-e7a7e7fb048f732eb685	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-4900000000-e34a5c59b0cce2170e4f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-271db1608159a875a61c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-e357308e88e379d8eb0b	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-ce70e056e1f4cfdf3761	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-9beba85555a54c1f672e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kui-7900000000-c36b8119a51196a1f474	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-0d126f50596b5c4ae9ec	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-d5b63c4616a3ca6983c2	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-2900000000-f4d199baa93fba2d315c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-ac524f6f858437766e2f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1900000000-1064492c92995ca99566	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9300000000-62b87115059cfc657adc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-a956a3a0009c6965897a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-7b07769eadb95204ac58	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0900000000-fea25d8ed304aa380484	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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
Metabolism and Physiological Effects of Indoxyl Sulfate

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012717	Indole	Indoxyl	Cyp2e1	oxidation	PubMed	11808865
MMDBr0012719	Indoxyl	Indoxyl sulfate	Sulfotransferase family, cytosolic, 1a, phenol-preferring, member 1	Indoxyl Sulfate Formation from Indoxyl	RHEA; KEGG; VMH	11808865
MMDBr0012720	Indoxyl	Indoxyl glucuronide	Not Available	conjugation; phase-II biotransformation; glucuronide-conjugation		Manually annotated by MiMeDB team
MMDBr0006139	Water	Hydrogen Ion	Cytochrome p450, family 2, subfamily e, polypeptide 1	Indoxyl Formation from Indole	VMH	30371894
MMDBr0016636	Hydrogen Ion	Water	Indole-3-acetate monooxygenase	Oxygenation	RHEA	34755880
MMDBr0016637	Hydrogen Ion	Water	Indole-3-acetate monooxygenase	Oxygenation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Oxidative stress	induces	Cell culture	HL-60 human macrophage cell	PubMed	32879256
Phagocytic activity	impairs	Cell culture	HL-60 human macrophage cell	PubMed	32879256

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	2	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
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0004094

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Indoxyl

METLIN ID

7014

PubChem Compound

50591

PDB ID

Not Available

ChEBI ID

17840

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Delisle GJ, Ley A: Rapid detection of Escherichia coli in urine samples by a new chromogenic beta-glucuronidase assay. J Clin Microbiol. 1989 Apr;27(4):778-9. doi: 10.1128/jcm.27.4.778-779.1989. [PubMed:2656750 ]
Achtergael W, Michielsen D, Gorus FK, Gerlo E: Indoxyl sulphate and the purple urine bag syndrome: a case report. Acta Clin Belg. 2006 Jan-Feb;61(1):38-41. doi: 10.1179/acb.2006.008. [PubMed:16673616 ]

Showing metabocard for Indoxyl (MMDBc0048025)

MOL for #<Metabolite:0x00007fa4e1b31e78>

3D MOL for #<Metabolite:0x00007fa4e1b31e78>

3D SDF for #<Metabolite:0x00007fa4e1b31e78>

3D-SDF for #<Metabolite:0x00007fa4e1b31e78>

PDB for #<Metabolite:0x00007fa4e1b31e78>

3D PDB for #<Metabolite:0x00007fa4e1b31e78>

SMILES for #<Metabolite:0x00007fa4e1b31e78>

INCHI for #<Metabolite:0x00007fa4e1b31e78>

Structure for #<Metabolite:0x00007fa4e1b31e78>

3D Structure for #<Metabolite:0x00007fa4e1b31e78>