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Showing NP-Card for methyl 1-methoxyindole-3-carboxylate (NP0192385)

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Record Information
Version2.0
Created at2022-09-04 09:35:17 UTC
Updated at2022-09-04 09:35:17 UTC
NP-MRD IDNP0192385
Secondary Accession NumbersNone
Natural Product Identification
Common Namemethyl 1-methoxyindole-3-carboxylate
DescriptionMethyl 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Methyl 1-methoxy-1H-indole-3-carboxylate has been detected, but not quantified in, herbs and spices. methyl 1-methoxyindole-3-carboxylate is found in Leptosphaeria maculans. This could make methyl 1-methoxy-1H-indole-3-carboxylate a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0192385 (methyl 1-methoxyindole-3-carboxylate)


  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
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3D MOL for NP0192385 (methyl 1-methoxyindole-3-carboxylate)

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3D SDF for NP0192385 (methyl 1-methoxyindole-3-carboxylate)

  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>
NP0192385

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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3D-SDF for NP0192385 (methyl 1-methoxyindole-3-carboxylate)
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PDB for NP0192385 (methyl 1-methoxyindole-3-carboxylate)
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

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3D PDB for NP0192385 (methyl 1-methoxyindole-3-carboxylate)
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SMILES for NP0192385 (methyl 1-methoxyindole-3-carboxylate)
CON1C=C(C(=O)OC)C2=CC=CC=C12
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INCHI for NP0192385 (methyl 1-methoxyindole-3-carboxylate)
InChI=1S/C11H11NO3/c1-14-11(13)9-7-12(15-2)10-6-4-3-5-8(9)10/h3-7H,1-2H3
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View in JSmol
Synonyms
ValueSource
Methyl 1-methoxy-1H-indole-3-carboxylic acidGenerator
PhytoalexinsHMDB
Chemical FormulaC11H11NO3
Average Mass205.2099 Da
Monoisotopic Mass205.07389 Da
IUPAC Namemethyl 1-methoxy-1H-indole-3-carboxylate
Traditional Namemethyl 1-methoxyindole-3-carboxylate
CAS Registry NumberNot Available
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 KeyJAAYVMHPQAMBJS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Leptosphaeria maculansLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndolecarboxylic acids and derivatives  
Direct ParentIndolecarboxylic 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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.27ALOGPS
logP1.78ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.83 m³·mol⁻¹ChemAxon
Polarizability21.18 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032755  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010722  
KNApSAcK IDNot Available
Chemspider ID8640951  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10465540  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]