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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 13:49:24 UTC

Update Date

2023-02-21 17:16:57 UTC

HMDB ID

HMDB0004186

Secondary Accession Numbers

HMDB04186

Metabolite Identification

Common Name

3-Methyldioxyindole

Description

3-Methyldioxyindole 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. 3-Methyldioxyindole has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-methyldioxyindole a potential biomarker for the consumption of these foods. 3-Methyldioxyindole is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 3-Methyldioxyindole.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      42.031 -44.449   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      43.223 -46.591   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      40.784 -47.831   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      40.310 -43.886   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      40.784 -45.352   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      41.683 -46.591   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      39.327 -47.361   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      39.327 -45.821   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.993 -48.131   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.993 -45.051   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.659 -47.361   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.659 -45.821   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    6    7                                                       
CONECT    4    5                                                            
CONECT    5    1    4    6    8                                             
CONECT    6    2    3    5                                                  
CONECT    7    3    8    9                                                  
CONECT    8    5    7   10                                                  
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,3-Dihydro-3-hydroxy-3-methyl-2H-indol-2-one	ChEBI
3-Hydroxy-3-methyloxindole	Kegg
3-Hydroxy-3-methyl-2-indolinone	HMDB
3-Hydroxy-3-methyl-oxindole	HMDB
3-Methyldioxyindole	ChEBI

Chemical Formula

C₉H₉NO₂

Average Molecular Weight

163.1733

Monoisotopic Molecular Weight

163.063328537

IUPAC Name

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

Traditional Name

3-hydroxy-3-methyloxindole

CAS Registry Number

3040-34-4

SMILES

CC1(O)C(=O)NC2=CC=CC=C12

InChI Identifier

InChI=1S/C9H9NO2/c1-9(12)6-4-2-3-5-7(6)10-8(9)11/h2-5,12H,1H3,(H,10,11)

InChI Key

XCHBYBKNFIOSBB-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
Tertiary alcohol
Carboxamide group
Lactam
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:28254 )
hydroxyindoles (CHEBI:28254 )
methylindole (CHEBI:28254 )

Ontology

Not Available

Endogenous (HMDB: HMDB0004186)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	11 g/L	ALOGPS
logP	0.88	ALOGPS
logP	0.79	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	11.78	ChemAxon
pKa (Strongest Basic)	-4.1	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	45.64 m³·mol⁻¹	ChemAxon
Polarizability	16.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DarkChem	[M+H]+	135.247	31661259
DarkChem	[M-H]-	131.475	31661259
DeepCCS	[M-2H]-	170.202	30932474
DeepCCS	[M+Na]+	145.74	30932474
AllCCS	[M+H]+	133.5	32859911
AllCCS	[M+H-H2O]+	128.9	32859911
AllCCS	[M+NH4]+	137.8	32859911
AllCCS	[M+Na]+	139.0	32859911
AllCCS	[M-H]-	133.0	32859911
AllCCS	[M+Na-2H]-	133.7	32859911
AllCCS	[M+HCOO]-	134.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.0 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7049 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.28 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1287.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	298.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	94.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	53.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	265.3 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	465.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	100.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	717.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	197.0 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	958.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	234.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	255.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	401.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	230.7 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	122.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyldioxyindole	CC1(O)C(=O)NC2=CC=CC=C12	2833.9	Standard polar	33892256
3-Methyldioxyindole	CC1(O)C(=O)NC2=CC=CC=C12	1518.6	Standard non polar	33892256
3-Methyldioxyindole	CC1(O)C(=O)NC2=CC=CC=C12	1595.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyldioxyindole,1TMS,isomer #1	CC1(O[Si](C)(C)C)C(=O)NC2=CC=CC=C21	1640.5	Semi standard non polar	33892256
3-Methyldioxyindole,1TMS,isomer #2	CC1(O)C(=O)N([Si](C)(C)C)C2=CC=CC=C21	1561.3	Semi standard non polar	33892256
3-Methyldioxyindole,2TMS,isomer #1	CC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=CC=C21	1626.6	Semi standard non polar	33892256
3-Methyldioxyindole,2TMS,isomer #1	CC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=CC=C21	1679.0	Standard non polar	33892256
3-Methyldioxyindole,2TMS,isomer #1	CC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=CC=C21	1827.4	Standard polar	33892256
3-Methyldioxyindole,1TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)C(=O)NC2=CC=CC=C21	1888.2	Semi standard non polar	33892256
3-Methyldioxyindole,1TBDMS,isomer #2	CC1(O)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C21	1816.6	Semi standard non polar	33892256
3-Methyldioxyindole,2TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2123.4	Semi standard non polar	33892256
3-Methyldioxyindole,2TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2137.4	Standard non polar	33892256
3-Methyldioxyindole,2TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C21	2062.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyldioxyindole GC-MS (Non-derivatized) - 70eV, Positive	splash10-00y1-1900000000-d9eb36be4ce6900f7939	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyldioxyindole GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-2930000000-0812c5ed6e0081fdad01	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyldioxyindole 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-Methyldioxyindole 10V, Positive-QTOF	splash10-03di-0900000000-66dd3708cda64af1a7bc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyldioxyindole 20V, Positive-QTOF	splash10-03di-0900000000-3648ce4f197e97785ebc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyldioxyindole 40V, Positive-QTOF	splash10-02tc-9600000000-2f575fffc3e04a1ed6a9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyldioxyindole 10V, Negative-QTOF	splash10-03di-0900000000-c46a2d6959518a479466	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyldioxyindole 20V, Negative-QTOF	splash10-03di-2900000000-b607b16fa1f1262fe500	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyldioxyindole 40V, Negative-QTOF	splash10-00kf-9600000000-57882774394baf3844c9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyldioxyindole 10V, Negative-QTOF	splash10-03di-0900000000-e7a61b498c894247b9c2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyldioxyindole 20V, Negative-QTOF	splash10-01ox-0900000000-d4c96ef21e6c15e6a3da	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyldioxyindole 40V, Negative-QTOF	splash10-0006-9300000000-1eb005b5ee3a8efdff3c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyldioxyindole 10V, Positive-QTOF	splash10-03dj-0900000000-a30ecbbff837069bc50b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyldioxyindole 20V, Positive-QTOF	splash10-00kb-0900000000-2bc49d662acb4be7b267	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyldioxyindole 40V, Positive-QTOF	splash10-0uxu-9800000000-d6031ffbbaa8b0304c5c	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7024

PubChem Compound

151066

PDB ID

Not Available

ChEBI ID

28254

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Morita, Yuhei; Kameda, Katsuzo; Mizuno, Masayuki. Phytoperoxidase. XVI. Aerobic destruction of indole-3-acetic acid catalyzed by crystalline Japanese-radish peroxidase a and c. Agr. Biol. Chem. (1962), 26 442-6.

Material Safety Data Sheet (MSDS)

Not Available

General References

Albrecht CF, Chorn DJ, Wessels PL: Detection of 3-hydroxy-3-methyloxindole in human urine. Life Sci. 1989;45(12):1119-26. [PubMed:2796599 ]

Showing metabocard for 3-Methyldioxyindole (HMDB0004186)

MOL for HMDB0004186 (3-Methyldioxyindole)

3D MOL for HMDB0004186 (3-Methyldioxyindole)

3D SDF for HMDB0004186 (3-Methyldioxyindole)

3D-SDF for HMDB0004186 (3-Methyldioxyindole)

PDB for HMDB0004186 (3-Methyldioxyindole)

3D PDB for HMDB0004186 (3-Methyldioxyindole)

SMILES for HMDB0004186 (3-Methyldioxyindole)

INCHI for HMDB0004186 (3-Methyldioxyindole)

Structure for HMDB0004186 (3-Methyldioxyindole)

3D Structure for HMDB0004186 (3-Methyldioxyindole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra