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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-01-04 22:31:31 UTC

Update Date

2022-09-22 18:34:33 UTC

HMDB ID

HMDB0240741

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Hydroxy-2-oxoindole

Description

3-Hydroxy-2-oxoindole is an oxidized indole derivative. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. 3-hydroxy-2-oxoindole is a naturally occurring indole metabolite found in human urine (PMID: 11722560 ). It is a reduced form of the more abundant naturally occurring indole metabolite known as isatin (which is derived from the gut microbial metabolism of tryptophan). 3-hydroxy-2-oxoindole is generated via the activity of the enzyme known as isatin reductase, which is found in the liver and kidney (PMID: 11722560 ). It exhibits modest monoamine oxidase A and B inhibitory activity.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,3-Dihydro-3-hydroxy-2H-indol-2-one	ChEBI
3-Hydroxy-2-indolinone	ChEBI
3-Hydroxy-indolin-2-one	ChEBI
3-Hydroxyoxindole	ChEBI
Dioxindole	ChEBI
3-Hydroxy-2-oxoindole	MeSH

Chemical Formula

C₈H₇NO₂

Average Molecular Weight

149.149

Monoisotopic Molecular Weight

149.047678469

IUPAC Name

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

Traditional Name

3-hydroxyoxindole

CAS Registry Number

Not Available

SMILES

OC1C(=O)NC2=CC=CC=C12

InChI Identifier

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

InChI Key

SGZFJWQQBHYNNF-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
Benzenoid
Carboxamide group
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxindole (CHEBI:28536 )
hydroxyindoles (CHEBI:28536 )
an indole derivative (CPD-6362 )

Ontology

Not Available

Exogenous (HMDB: HMDB0240741)

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	0.34	ALOGPS
logP	0.36	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	11.59	ChemAxon
pKa (Strongest Basic)	-4	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	40.92 m³·mol⁻¹	ChemAxon
Polarizability	14.52 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-2H]-	160.772	30932474
DeepCCS	[M+Na]+	136.091	30932474
AllCCS	[M+H]+	131.5	32859911
AllCCS	[M+H-H2O]+	126.8	32859911
AllCCS	[M+NH4]+	136.0	32859911
AllCCS	[M+Na]+	137.2	32859911
AllCCS	[M-H]-	128.1	32859911
AllCCS	[M+Na-2H]-	128.9	32859911
AllCCS	[M+HCOO]-	129.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.4616 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.7 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1165.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	316.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	84.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	51.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	246.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	394.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	188.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	666.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	96.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	888.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	210.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	451.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	294.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	167.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-2-oxoindole	OC1C(=O)NC2=CC=CC=C12	2873.7	Standard polar	33892256
3-Hydroxy-2-oxoindole	OC1C(=O)NC2=CC=CC=C12	1590.0	Standard non polar	33892256
3-Hydroxy-2-oxoindole	OC1C(=O)NC2=CC=CC=C12	1669.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-2-oxoindole,1TMS,isomer #1	C[Si](C)(C)OC1C(=O)NC2=CC=CC=C21	1684.6	Semi standard non polar	33892256
3-Hydroxy-2-oxoindole,1TMS,isomer #2	C[Si](C)(C)N1C(=O)C(O)C2=CC=CC=C21	1567.3	Semi standard non polar	33892256
3-Hydroxy-2-oxoindole,2TMS,isomer #1	C[Si](C)(C)OC1C(=O)N([Si](C)(C)C)C2=CC=CC=C21	1626.7	Semi standard non polar	33892256
3-Hydroxy-2-oxoindole,2TMS,isomer #1	C[Si](C)(C)OC1C(=O)N([Si](C)(C)C)C2=CC=CC=C21	1693.0	Standard non polar	33892256
3-Hydroxy-2-oxoindole,2TMS,isomer #1	C[Si](C)(C)OC1C(=O)N([Si](C)(C)C)C2=CC=CC=C21	1823.3	Standard polar	33892256
3-Hydroxy-2-oxoindole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(=O)NC2=CC=CC=C21	1922.1	Semi standard non polar	33892256
3-Hydroxy-2-oxoindole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)C(O)C2=CC=CC=C21	1828.1	Semi standard non polar	33892256
3-Hydroxy-2-oxoindole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2095.8	Semi standard non polar	33892256
3-Hydroxy-2-oxoindole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2145.7	Standard non polar	33892256
3-Hydroxy-2-oxoindole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2107.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-2-oxoindole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - 3-Hydroxy-2-oxoindole 10V, Positive-QTOF	splash10-001i-0900000000-d299140f3c00196767e2	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-oxoindole 20V, Positive-QTOF	splash10-0f89-0900000000-228af5c4254a2dd88c1a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-oxoindole 40V, Positive-QTOF	splash10-0uxu-9600000000-fc4f192f11ac024ed51f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-oxoindole 10V, Negative-QTOF	splash10-014i-2900000000-cedc25ee85fac8ae7ed4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-oxoindole 20V, Negative-QTOF	splash10-0006-9300000000-9661172b1abd313a1532	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-2-oxoindole 40V, Negative-QTOF	splash10-0006-9300000000-dc6289c288519f29a769	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

Not Available

Chemspider ID

5872

KEGG Compound ID

C11130

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6097

PDB ID

Not Available

ChEBI ID

28536

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

Usami N, Kitahara K, Ishikura S, Nagano M, Sakai S, Hara A: Characterization of a major form of human isatin reductase and the reduced metabolite. Eur J Biochem. 2001 Nov;268(22):5755-63. doi: 10.1046/j.0014-2956.2001.02510.x. [PubMed:11722560 ]

Showing metabocard for 3-Hydroxy-2-oxoindole (HMDB0240741)

MOL for HMDB0240741 (3-Hydroxy-2-oxoindole)

3D MOL for HMDB0240741 (3-Hydroxy-2-oxoindole)

3D SDF for HMDB0240741 (3-Hydroxy-2-oxoindole)

3D-SDF for HMDB0240741 (3-Hydroxy-2-oxoindole)

PDB for HMDB0240741 (3-Hydroxy-2-oxoindole)

3D PDB for HMDB0240741 (3-Hydroxy-2-oxoindole)

SMILES for HMDB0240741 (3-Hydroxy-2-oxoindole)

INCHI for HMDB0240741 (3-Hydroxy-2-oxoindole)

Structure for HMDB0240741 (3-Hydroxy-2-oxoindole)

3D Structure for HMDB0240741 (3-Hydroxy-2-oxoindole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra