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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:49:12 UTC

Update Date

2022-09-22 18:34:41 UTC

HMDB ID

HMDB0341227

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1H-Indole-2-carboxylic acid, ethyl ester

Description

ethyl 1H-indole-2-carboxylate belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. ethyl 1H-indole-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004191602172D          

 14 15  0  0  0  0            999 V2000
   -1.8212    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
  9  8  1  0  0  0  0
 10  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14  2  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341227

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1=CC2=CC=CC=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO2/c1-2-14-11(13)10-7-8-5-3-4-6-9(8)12-10/h3-7,12H,2H2,1H3

> <INCHI_KEY>
QQXQAEWRSVZPJM-UHFFFAOYSA-N

> <FORMULA>
C11H11NO2

> <MOLECULAR_WEIGHT>
189.214

> <EXACT_MASS>
189.078978598

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
20.559439649311447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 1H-indole-2-carboxylate

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.352293851333333

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.2537840543891

> <JCHEM_PKA_STRONGEST_BASIC>
-7.109642641480017

> <JCHEM_POLAR_SURFACE_AREA>
42.09

> <JCHEM_REFRACTIVITY>
53.795899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 1H-indole-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0      -3.400   5.510   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      -1.090   1.509   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.090   4.177   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   14                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    9                                                       
CONECT    7    8   10                                                       
CONECT    8    5    7    9                                                  
CONECT    9    6    8   12                                                  
CONECT   10    7   11   12                                                  
CONECT   11   10   13   14                                                  
CONECT   12    9   10                                                       
CONECT   13   11                                                            
CONECT   14    2   11                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl 1H-indole-2-carboxylic acid	Generator

Chemical Formula

C₁₁H₁₁NO₂

Average Molecular Weight

189.214

Monoisotopic Molecular Weight

189.078978598

IUPAC Name

ethyl 1H-indole-2-carboxylate

Traditional Name

ethyl 1H-indole-2-carboxylate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C1=CC2=CC=CC=C2N1

InChI Identifier

InChI=1S/C11H11NO2/c1-2-14-11(13)10-7-8-5-3-4-6-9(8)12-10/h3-7,12H,2H2,1H3

InChI Key

QQXQAEWRSVZPJM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids and derivatives

Alternative Parents

Substituents

Indolecarboxylic acid derivative
Indole
Pyrrole-2-carboxylic acid or derivatives
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid ester
Monocarboxylic acid or derivatives
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

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	3.01	ALOGPS
logP	2.35	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	11.25	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.8 m³·mol⁻¹	ChemAxon
Polarizability	20.56 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 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 - 1H-Indole-2-carboxylic acid, ethyl ester 10V, Positive-QTOF	splash10-0006-0900000000-e827e46182f67024f24b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1H-Indole-2-carboxylic acid, ethyl ester 20V, Positive-QTOF	splash10-0006-1900000000-bf3168a0bd2030e67182	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1H-Indole-2-carboxylic acid, ethyl ester 40V, Positive-QTOF	splash10-014i-3900000000-72455314a639e2f61ddb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1H-Indole-2-carboxylic acid, ethyl ester 10V, Negative-QTOF	splash10-000l-1900000000-7e9ed2e193ba80fc592d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1H-Indole-2-carboxylic acid, ethyl ester 20V, Negative-QTOF	splash10-000f-2900000000-a56bfc40ecdc5086a467	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1H-Indole-2-carboxylic acid, ethyl ester 40V, Negative-QTOF	splash10-0297-5900000000-555bb537f1a5fff7e3a3	2016-08-03	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73125

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

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for 1H-Indole-2-carboxylic acid, ethyl ester (HMDB0341227)

MOL for HMDB0341227 (1H-Indole-2-carboxylic acid, ethyl ester)

3D MOL for HMDB0341227 (1H-Indole-2-carboxylic acid, ethyl ester)

3D SDF for HMDB0341227 (1H-Indole-2-carboxylic acid, ethyl ester)

3D-SDF for HMDB0341227 (1H-Indole-2-carboxylic acid, ethyl ester)

PDB for HMDB0341227 (1H-Indole-2-carboxylic acid, ethyl ester)

3D PDB for HMDB0341227 (1H-Indole-2-carboxylic acid, ethyl ester)

SMILES for HMDB0341227 (1H-Indole-2-carboxylic acid, ethyl ester)

INCHI for HMDB0341227 (1H-Indole-2-carboxylic acid, ethyl ester)

Structure for HMDB0341227 (1H-Indole-2-carboxylic acid, ethyl ester)

3D Structure for HMDB0341227 (1H-Indole-2-carboxylic acid, ethyl ester)

Predicted Kovats Retention Indices

MS/MS Spectra