Jump To Section:

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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:36 UTC

Update Date

2023-02-21 17:22:38 UTC

HMDB ID

HMDB0032755

Secondary Accession Numbers

HMDB32755

Metabolite Identification

Common Name

Methyl 1-methoxy-1H-indole-3-carboxylate

Description

Methyl 1-methoxy-1H-indole-3-carboxylate, also known as phytoalexins, 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. Methyl 1-methoxy-1H-indole-3-carboxylate has been detected, but not quantified in, herbs and spices. This could make methyl 1-methoxy-1H-indole-3-carboxylate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Methyl 1-methoxy-1H-indole-3-carboxylate.

Structure

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

  Mrv0541 05061306402D          

 15 16  0  0  0  0            999 V2000
    1.1809   -1.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    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
    0.6538    1.5229    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
    1.1387    0.8555    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
    0.8838    0.0709    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
    0.0768   -0.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  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
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14  1  1  0  0  0  0
 14 11  1  0  0  0  0
 15  2  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032755

> <DATABASE_NAME>
hmdb

> <SMILES>
CON1C=C(C(=O)OC)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO3/c1-14-11(13)9-7-12(15-2)10-6-4-3-5-8(9)10/h3-7H,1-2H3

> <INCHI_KEY>
JAAYVMHPQAMBJS-UHFFFAOYSA-N

> <FORMULA>
C11H11NO3

> <MOLECULAR_WEIGHT>
205.2099

> <EXACT_MASS>
205.073893223

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
21.175688141338554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 1-methoxy-1H-indole-3-carboxylate

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
1.7811404510000002

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.644491653142235

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
56.827400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1-methoxyindole-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.204  -2.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.143   5.873   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       1.220   2.843   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       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.650   0.132   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       0.143  -0.188   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.680  -1.012   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   15                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4   10                                                       
CONECT    7    9   12                                                       
CONECT    8    5    9   10                                                  
CONECT    9    7    8   11                                                  
CONECT   10    6    8   12                                                  
CONECT   11    9   13   14                                                  
CONECT   12    7   10   15                                                  
CONECT   13   11                                                            
CONECT   14    1   11                                                       
CONECT   15    2   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0032755
HETATM    1  C1  UNL     1       4.668  -0.707  -0.227  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.267  -0.945  -0.091  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.349   0.071  -0.010  1.00  0.00           C  
HETATM    4  O2  UNL     1       2.781   1.252  -0.060  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.903  -0.167   0.131  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.247  -1.375   0.202  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.085  -1.198   0.329  1.00  0.00           N  
HETATM    8  O3  UNL     1      -2.075  -2.165   0.431  1.00  0.00           O  
HETATM    9  C5  UNL     1      -2.984  -2.318  -0.646  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.277   0.128   0.338  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.436   0.870   0.444  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.377   2.247   0.428  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.162   2.893   0.307  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.014   2.162   0.199  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.080   0.791   0.218  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.017  -1.447  -0.988  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.195  -0.825   0.734  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.871   0.305  -0.621  1.00  0.00           H  
HETATM   19  H4  UNL     1       0.695  -2.359   0.166  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.131  -3.408  -0.799  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.930  -1.815  -0.343  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.578  -1.915  -1.598  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.413   0.377   0.541  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.290   2.850   0.512  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.124   3.981   0.296  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.935   2.716   0.107  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   15
CONECT    6    7   19
CONECT    7    8   10
CONECT    8    9
CONECT    9   20   21   22
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 1-methoxy-1H-indole-3-carboxylic acid	Generator
Phytoalexins	HMDB

Chemical Formula

C₁₁H₁₁NO₃

Average Molecular Weight

205.2099

Monoisotopic Molecular Weight

205.073893223

IUPAC Name

methyl 1-methoxy-1H-indole-3-carboxylate

Traditional Name

methyl 1-methoxyindole-3-carboxylate

CAS Registry Number

18377-50-9

SMILES

CON1C=C(C(=O)OC)C2=CC=CC=C12

InChI Identifier

InChI=1S/C11H11NO3/c1-14-11(13)9-7-12(15-2)10-6-4-3-5-8(9)10/h3-7H,1-2H3

InChI Key

JAAYVMHPQAMBJS-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-3-carboxylic acid or derivatives
Substituted pyrrole
Benzenoid
Pyrrole
Methyl ester
Vinylogous amide
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032755)
Cytoplasm (HMDB: HMDB0032755)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032755)

Source

Exogenous

Exogenous (HMDB: HMDB0032755)

Food

Food (HMDB: HMDB0032755)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0032755)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032755)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	40 - 41 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	853.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.85 g/L	ALOGPS
logP	2.27	ALOGPS
logP	1.78	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.83 m³·mol⁻¹	ChemAxon
Polarizability	21.18 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]+	147.672	31661259
DarkChem	[M-H]-	145.274	31661259
DeepCCS	[M-2H]-	170.527	30932474
DeepCCS	[M+Na]+	145.707	30932474
AllCCS	[M+H]+	144.0	32859911
AllCCS	[M+H-H2O]+	139.8	32859911
AllCCS	[M+NH4]+	147.9	32859911
AllCCS	[M+Na]+	149.0	32859911
AllCCS	[M-H]-	145.3	32859911
AllCCS	[M+Na-2H]-	145.4	32859911
AllCCS	[M+HCOO]-	145.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl 1-methoxy-1H-indole-3-carboxylate	CON1C=C(C(=O)OC)C2=CC=CC=C12	2767.8	Standard polar	33892256
Methyl 1-methoxy-1H-indole-3-carboxylate	CON1C=C(C(=O)OC)C2=CC=CC=C12	1714.8	Standard non polar	33892256
Methyl 1-methoxy-1H-indole-3-carboxylate	CON1C=C(C(=O)OC)C2=CC=CC=C12	1848.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0095-1900000000-8cfd3846154530d5b9a7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate 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 - Methyl 1-methoxy-1H-indole-3-carboxylate 10V, Positive-QTOF	splash10-0a4i-0090000000-61fc39151a32b107e2ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate 20V, Positive-QTOF	splash10-0a4i-0490000000-5bca0ac14fb28c9be013	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate 40V, Positive-QTOF	splash10-0096-0900000000-38f9d5ebc26ae03fb775	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate 10V, Negative-QTOF	splash10-0udi-0290000000-98bf18bd9baeea49f4e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate 20V, Negative-QTOF	splash10-00di-0920000000-2fdf9aca0b0cfa66ea43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate 40V, Negative-QTOF	splash10-00bc-6900000000-d65fdf8f5289eed3261f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate 10V, Positive-QTOF	splash10-05fr-0980000000-127b72000982a957381a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate 20V, Positive-QTOF	splash10-05fu-0930000000-d1d8aa36d2510b3c34ff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate 40V, Positive-QTOF	splash10-0f6y-1900000000-8f6333600471498206e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate 10V, Negative-QTOF	splash10-0udi-0090000000-fb252b861176302082ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate 20V, Negative-QTOF	splash10-00kb-0910000000-20e18aa9951d1d720386	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 1-methoxy-1H-indole-3-carboxylate 40V, Negative-QTOF	splash10-014i-0900000000-65319e1adbe481146b40	2021-09-22	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]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB010722

KNApSAcK ID

Not Available

Chemspider ID

8640951

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10465540

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1831341

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Methyl 1-methoxy-1H-indole-3-carboxylate (HMDB0032755)

MOL for HMDB0032755 (Methyl 1-methoxy-1H-indole-3-carboxylate)

3D MOL for HMDB0032755 (Methyl 1-methoxy-1H-indole-3-carboxylate)

3D SDF for HMDB0032755 (Methyl 1-methoxy-1H-indole-3-carboxylate)

3D-SDF for HMDB0032755 (Methyl 1-methoxy-1H-indole-3-carboxylate)

PDB for HMDB0032755 (Methyl 1-methoxy-1H-indole-3-carboxylate)

3D PDB for HMDB0032755 (Methyl 1-methoxy-1H-indole-3-carboxylate)

SMILES for HMDB0032755 (Methyl 1-methoxy-1H-indole-3-carboxylate)

INCHI for HMDB0032755 (Methyl 1-methoxy-1H-indole-3-carboxylate)

Structure for HMDB0032755 (Methyl 1-methoxy-1H-indole-3-carboxylate)

3D Structure for HMDB0032755 (Methyl 1-methoxy-1H-indole-3-carboxylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra