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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:49:20 UTC

Update Date

2021-09-26 22:56:07 UTC

HMDB ID

HMDB0246809

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-Hydroxyoxindole

Description

5-Hydroxyoxindole belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole. Based on a literature review a significant number of articles have been published on 5-Hydroxyoxindole. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-hydroxyoxindole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-Hydroxyoxindole is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₈H₇NO₂

Average Molecular Weight

149.149

Monoisotopic Molecular Weight

149.047678469

IUPAC Name

5-hydroxy-2,3-dihydro-1H-indol-2-one

Traditional Name

5-hydroxy-1,3-dihydroindol-2-one

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(NC(=O)C2)C=C1

InChI Identifier

InChI=1S/C8H7NO2/c10-6-1-2-7-5(3-6)4-8(11)9-7/h1-3,10H,4H2,(H,9,11)

InChI Key

ZGTUSQAQXWSMDW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolines

Direct Parent

Indolines

Alternative Parents

Substituents

Dihydroindole
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.27	ALOGPS
logP	0.77	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	9.38	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.57 m³·mol⁻¹	ChemAxon
Polarizability	14.69 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	130.098	30932474
DeepCCS	[M-H]-	127.082	30932474
DeepCCS	[M-2H]-	164.078	30932474
DeepCCS	[M+Na]+	139.498	30932474
AllCCS	[M+H]+	133.4	32859911
AllCCS	[M+H-H2O]+	128.9	32859911
AllCCS	[M+NH4]+	137.6	32859911
AllCCS	[M+Na]+	138.8	32859911
AllCCS	[M-H]-	129.4	32859911
AllCCS	[M+Na-2H]-	130.4	32859911
AllCCS	[M+HCOO]-	131.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxyoxindole	OC1=CC2=C(NC(=O)C2)C=C1	2973.5	Standard polar	33892256
5-Hydroxyoxindole	OC1=CC2=C(NC(=O)C2)C=C1	1692.8	Standard non polar	33892256
5-Hydroxyoxindole	OC1=CC2=C(NC(=O)C2)C=C1	1859.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxyoxindole,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)CC(=O)N2[Si](C)(C)C	1811.8	Semi standard non polar	33892256
5-Hydroxyoxindole,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)CC(=O)N2[Si](C)(C)C	1807.0	Standard non polar	33892256
5-Hydroxyoxindole,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)CC(=O)N2[Si](C)(C)C	1945.2	Standard polar	33892256
5-Hydroxyoxindole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC(=O)N2[Si](C)(C)C(C)(C)C	2290.0	Semi standard non polar	33892256
5-Hydroxyoxindole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC(=O)N2[Si](C)(C)C(C)(C)C	2286.3	Standard non polar	33892256
5-Hydroxyoxindole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC(=O)N2[Si](C)(C)C(C)(C)C	2185.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxyoxindole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aba-0900000000-c28d9dfbef47f6c66ad1	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxyoxindole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxyoxindole GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxyoxindole GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxyoxindole GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxyoxindole GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyoxindole 10V, Positive-QTOF	splash10-0udi-0900000000-e9c84d792f3855d1e622	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyoxindole 20V, Positive-QTOF	splash10-0udi-3900000000-942b5e59f16e6992889b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyoxindole 40V, Positive-QTOF	splash10-0059-9400000000-29504acf0bdbf23c49fa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyoxindole 10V, Negative-QTOF	splash10-0002-0900000000-d32a0a3b410ab4200586	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyoxindole 20V, Negative-QTOF	splash10-0002-0900000000-9b18d8e2f04cabba82e6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyoxindole 40V, Negative-QTOF	splash10-00kf-9300000000-287f402640eae63b2b21	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00048293

Chemspider ID

69404

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76955

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 5-Hydroxyoxindole (HMDB0246809)

MOL for HMDB0246809 (5-Hydroxyoxindole)

3D MOL for HMDB0246809 (5-Hydroxyoxindole)

3D SDF for HMDB0246809 (5-Hydroxyoxindole)

3D-SDF for HMDB0246809 (5-Hydroxyoxindole)

PDB for HMDB0246809 (5-Hydroxyoxindole)

3D PDB for HMDB0246809 (5-Hydroxyoxindole)

SMILES for HMDB0246809 (5-Hydroxyoxindole)

INCHI for HMDB0246809 (5-Hydroxyoxindole)

Structure for HMDB0246809 (5-Hydroxyoxindole)

3D Structure for HMDB0246809 (5-Hydroxyoxindole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra