NP-MRD: Showing NP-Card for Ethyl 3-indoleacetate (NP0333370)

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Record Information

Version

1.0

Created at

2024-06-05 16:48:19 UTC

Updated at

2024-06-07 00:01:37 UTC

NP-MRD ID

NP0333370

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ethyl 3-indoleacetate

Description

Ethyl 2-(1H-indol-3-yl)acetate belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. Ethyl 2-(1H-indol-3-yl)acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 09041212562D          

 15 16  0  0  0  0            999 V2000
   -1.3921    4.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6776    4.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9959    3.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5479    3.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1889    3.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2930    4.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658    4.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2665    5.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1803    4.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9340    4.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860    4.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7513    4.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0735    5.4598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7513    5.2928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0369    4.0553    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
  9  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  2  0  0  0  0
 10  9  1  0  0  0  0
 11  6  2  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 15  2  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333370

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)CC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H13NO2/c1-2-15-12(14)7-9-8-13-11-6-4-3-5-10(9)11/h3-6,8,13H,2,7H2,1H3

> <INCHI_KEY>
HUDBDWIQSIGUDI-UHFFFAOYSA-N

> <FORMULA>
C12H13NO2

> <MOLECULAR_WEIGHT>
203.2371

> <EXACT_MASS>
203.094628665

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
21.909222385105984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 2-(1H-indol-3-yl)acetate

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
2.2124581089999995

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.044116761537524

> <JCHEM_PKA_STRONGEST_BASIC>
-7.086354245392252

> <JCHEM_POLAR_SURFACE_AREA>
42.09

> <JCHEM_REFRACTIVITY>
57.969800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 2-(1H-indol-3-yl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   15                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   11                                                       
CONECT    7    9   12                                                       
CONECT    8    9   13                                                       
CONECT    9    7    8   10                                                  
CONECT   10    5    9   11                                                  
CONECT   11    6   10   13                                                  
CONECT   12    7   14   15                                                  
CONECT   13    8   11                                                       
CONECT   14   12                                                            
CONECT   15    2   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
Ethyl 2-(1H-indol-3-yl)acetic acid	Generator
Indole-3-acetic acid ethyl ester	MeSH
Ethyl 3-indoleacetic acid	Generator

Chemical Formula

C₁₂H₁₃NO₂

Average Mass

203.2371 Da

Monoisotopic Mass

203.09463 Da

IUPAC Name

ethyl 2-(1H-indol-3-yl)acetate

Traditional Name

ethyl 2-(1H-indol-3-yl)acetate

CAS Registry Number

Not Available

SMILES

CCOC(=O)CC1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C12H13NO2/c1-2-15-12(14)7-9-8-13-11-6-4-3-5-10(9)11/h3-6,8,13H,2,7H2,1H3

InChI Key

HUDBDWIQSIGUDI-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-05	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-05	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-05	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-05	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indole-3-acetic acid derivatives

Alternative Parents

Substituents

Indole-3-acetic acid derivative
3-alkylindole
Indole
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Carboxylic acid ester
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	3.04	ALOGPS
logP	2.21	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	15.04	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	4	ChemAxon
Refractivity	57.97 m³·mol⁻¹	ChemAxon
Polarizability	21.91 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

13067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ethyl 3-indoleacetate (NP0333370)

MOL for NP0333370 (Ethyl 3-indoleacetate)

3D MOL for NP0333370 (Ethyl 3-indoleacetate)

3D SDF for NP0333370 (Ethyl 3-indoleacetate)

3D-SDF for NP0333370 (Ethyl 3-indoleacetate)

PDB for NP0333370 (Ethyl 3-indoleacetate)

3D PDB for NP0333370 (Ethyl 3-indoleacetate)

SMILES for NP0333370 (Ethyl 3-indoleacetate)

INCHI for NP0333370 (Ethyl 3-indoleacetate)

Structure for NP0333370 (Ethyl 3-indoleacetate)

3D Structure for NP0333370 (Ethyl 3-indoleacetate)