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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 03:52:45 UTC

Update Date

2021-09-24 03:52:45 UTC

HMDB ID

HMDB0303691

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methyl oxindole-3-acetate

Description

methyl 2-(2-hydroxy-3H-indol-3-yl)acetate belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Based on a literature review very few articles have been published on methyl 2-(2-hydroxy-3H-indol-3-yl)acetate.

Structure

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

  Mrv0541 10181203232D          

 15 16  0  0  0  0            999 V2000
   -1.7270   -3.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9020   -3.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4895   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9020   -2.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7270   -2.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2790   -1.8132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0327   -2.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9465   -2.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1395   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472   -1.7363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5596   -3.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3881   -4.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012   -4.8802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6034   -4.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4319   -5.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303691

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)CC1C(O)=NC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO3/c1-15-10(13)6-8-7-4-2-3-5-9(7)12-11(8)14/h2-5,8H,6H2,1H3,(H,12,14)

> <INCHI_KEY>
OEGSDTIXVSKASM-UHFFFAOYSA-N

> <FORMULA>
C11H11NO3

> <MOLECULAR_WEIGHT>
205.2099

> <EXACT_MASS>
205.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.95652690738749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-(2-hydroxy-3H-indol-3-yl)acetate

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.612714091666667

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.212760323587414

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.122869795465155

> <JCHEM_PKA_STRONGEST_BASIC>
0.835177903648137

> <JCHEM_POLAR_SURFACE_AREA>
58.89

> <JCHEM_REFRACTIVITY>
55.95

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-(2-hydroxy-3H-indol-3-yl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-OCT-12         0                                  
HETATM    1  C   UNK     0      -3.224  -7.197   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.684  -7.197   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.914  -5.863   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.684  -4.529   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.224  -4.529   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -4.254  -3.385   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -5.661  -4.011   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.500  -5.543   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.994  -5.863   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.995  -3.241   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -6.645  -6.573   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.324  -8.079   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -7.469  -9.110   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -4.860  -8.555   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.540 -10.062   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9   11                                                  
CONECT    9    1    8    5                                                  
CONECT   10    7                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0303691
HETATM    1  C1  UNL     1       3.891  -0.752  -1.758  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.085  -0.699  -0.612  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.966   0.180  -0.554  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.777   0.866  -1.569  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.211   0.147   0.683  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.055   0.934   0.770  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.531   0.727   2.172  1.00  0.00           C  
HETATM    8  O3  UNL     1       0.188   1.124   3.290  1.00  0.00           O  
HETATM    9  N1  UNL     1      -1.652   0.155   2.190  1.00  0.00           N  
HETATM   10  C6  UNL     1      -2.101  -0.108   0.865  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.262  -0.703   0.383  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.532  -0.862  -0.959  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.598  -0.405  -1.864  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.441   0.189  -1.375  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.164   0.351  -0.025  1.00  0.00           C  
HETATM   16  H1  UNL     1       3.945   0.227  -2.291  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.571  -1.490  -2.514  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.910  -1.084  -1.430  1.00  0.00           H  
HETATM   19  H4  UNL     1       0.961  -0.906   0.981  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.937   0.462   1.497  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.088   2.015   0.552  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.737   1.976   3.316  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.971  -1.049   1.129  1.00  0.00           H  
HETATM   24  H9  UNL     1      -4.450  -1.330  -1.282  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.773  -0.510  -2.918  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.736   0.545  -2.117  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   19   20
CONECT    6    7   15   21
CONECT    7    8    9    9
CONECT    8   22
CONECT    9   10
CONECT   10   11   11   15
CONECT   11   12   23
CONECT   12   13   13   24
CONECT   13   14   25
CONECT   14   15   15   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl 2-(2-hydroxy-3H-indol-3-yl)acetic acid	Generator
Methyl oxindole-3-acetic acid	Generator

Chemical Formula

C₁₁H₁₁NO₃

Average Molecular Weight

205.2099

Monoisotopic Molecular Weight

205.073893223

IUPAC Name

methyl 2-(2-hydroxy-3H-indol-3-yl)acetate

Traditional Name

methyl 2-(2-hydroxy-3H-indol-3-yl)acetate

CAS Registry Number

Not Available

SMILES

COC(=O)CC1C(O)=NC2=C1C=CC=C2

InChI Identifier

InChI=1S/C11H11NO3/c1-15-10(13)6-8-7-4-2-3-5-9(7)12-11(8)14/h2-5,8H,6H2,1H3,(H,12,14)

InChI Key

OEGSDTIXVSKASM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
Indole
Dihydroindole
Benzenoid
Methyl ester
Carboxamide group
Carboxylic acid ester
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0303691)

Food

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

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	1.58	ALOGPS
logP	1.61	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.12	ChemAxon
pKa (Strongest Basic)	0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	55.95 m³·mol⁻¹	ChemAxon
Polarizability	20.96 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
AllCCS	[M+H]+	144.671	32859911
AllCCS	[M+H-H2O]+	140.518	32859911
AllCCS	[M+Na]+	149.651	32859911
AllCCS	[M+NH4]+	148.537	32859911
AllCCS	[M-H]-	146.378	32859911
AllCCS	[M+Na-2H]-	146.513	32859911
AllCCS	[M+HCOO]-	146.755	32859911
DeepCCS	[M+H]+	143.723	30932474
DeepCCS	[M-H]-	141.344	30932474
DeepCCS	[M-2H]-	175.838	30932474
DeepCCS	[M+Na]+	150.646	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl oxindole-3-acetate 10V, Positive-QTOF	splash10-0ab9-0950000000-6e7499a8b240eedbc6a9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl oxindole-3-acetate 20V, Positive-QTOF	splash10-0ac4-3920000000-8e6fac20faa078ec0402	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl oxindole-3-acetate 40V, Positive-QTOF	splash10-052g-4900000000-5858c2cec9925731a1e6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl oxindole-3-acetate 10V, Negative-QTOF	splash10-0udi-0590000000-51197a8172be48064cfc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl oxindole-3-acetate 20V, Negative-QTOF	splash10-0uk9-3950000000-07982b061aac0c7f2c39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl oxindole-3-acetate 40V, Negative-QTOF	splash10-0006-7900000000-4309e5ff523ebc735ff7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl oxindole-3-acetate 10V, Positive-QTOF	splash10-052b-0930000000-990520e0a772c44a418c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl oxindole-3-acetate 20V, Positive-QTOF	splash10-001i-0900000000-608c06658db35cac128a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl oxindole-3-acetate 40V, Positive-QTOF	splash10-0gb9-3900000000-0137f81fd4962829c229	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl oxindole-3-acetate 10V, Negative-QTOF	splash10-0udi-0690000000-7ca2e75b5e832383fd85	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl oxindole-3-acetate 20V, Negative-QTOF	splash10-00dl-0900000000-f4eeb8b22231da2cbad8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl oxindole-3-acetate 40V, Negative-QTOF	splash10-0f8c-3900000000-beafc79a2b88281c0c4b	2021-10-21	Wishart 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

FDB018476

KNApSAcK ID

Not Available

Chemspider ID

9462184

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for Methyl oxindole-3-acetate (HMDB0303691)

MOL for HMDB0303691 (Methyl oxindole-3-acetate)

3D MOL for HMDB0303691 (Methyl oxindole-3-acetate)

3D SDF for HMDB0303691 (Methyl oxindole-3-acetate)

3D-SDF for HMDB0303691 (Methyl oxindole-3-acetate)

PDB for HMDB0303691 (Methyl oxindole-3-acetate)

3D PDB for HMDB0303691 (Methyl oxindole-3-acetate)

SMILES for HMDB0303691 (Methyl oxindole-3-acetate)

INCHI for HMDB0303691 (Methyl oxindole-3-acetate)

Structure for HMDB0303691 (Methyl oxindole-3-acetate)

3D Structure for HMDB0303691 (Methyl oxindole-3-acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra