NP-MRD: Showing NP-Card for Indole-3-methyl acetate (NP0045455)

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Record Information

Version

2.0

Created at

2022-03-17 19:20:15 UTC

Updated at

2024-09-03 04:22:19 UTC

NP-MRD ID

NP0045455

Natural Product DOI

https://doi.org/10.57994/2818

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Indole-3-methyl acetate

Description

Indole-3-methyl acetate, also known as methyl 3-indolylacetate or methyl b-indoleacetic acid, 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. Indole-3-methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Indole-3-methyl acetate has been detected, but not quantified in, several different foods, such as japanese chestnuts, japanese persimmons, sweet oranges, gram beans, and common grapes. This could make indole-3-methyl acetate a potential biomarker for the consumption of these foods. Indole-3-methyl acetate is found in Brassica oleracea , Chamaecyparis lawsoniana, Citrus reticulata, Citrus unshiu , Cotinus coggygria, Dalbergia dolichopetala, Euphorbia escula, Glycine soja , Homo Sapiens, Lathyrus maritimus, Lygodium flexuosum , Nicotiana tabacum , Panax ginseng , Picea abies , Picea sitchensis , Pinus contorta , Pinus slyvestris, Pseudomonas amygdali, Pseudomonas savastanoi, Pseudotsuga menziesii, Quercus robur , Rhizopus suinus, Ricinus communis , Saccharomyces cerevisiae , Solanum lycopersicum , Vicia amurensis and Vigna unguiculata var. sesquipedalis . The methyl ester of indole-3-acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652301282019172D          

 14 15  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.617910000.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.0469 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045455

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO2/c1-14-11(13)6-8-7-12-10-5-3-2-4-9(8)10/h2-5,7,12H,6H2,1H3

> <INCHI_KEY>
KTHADMDGDNYQRX-UHFFFAOYSA-N

> <FORMULA>
C11H11NO2

> <MOLECULAR_WEIGHT>
189.2105

> <EXACT_MASS>
189.078978601

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.777863703154345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
1.8556501543333335

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.044118914611719

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0781988457999905

> <JCHEM_POLAR_SURFACE_AREA>
42.09

> <JCHEM_REFRACTIVITY>
53.2212

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1H-indol-3-ylacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JAN-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8669.1548664.625   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8667.8208666.935   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8670.4888665.395   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
beta-Indolylacetic acid methyl ester	ChEBI
Indole-3-acetic acid, methyl ester	ChEBI
Methyl 3-indolylacetate	ChEBI
Methyl beta-indoleacetate	ChEBI
Methyl beta-indolylacetate	ChEBI
Methyl indol-3-ylacetate	ChEBI
b-Indolylacetate methyl ester	Generator
b-Indolylacetic acid methyl ester	Generator
beta-Indolylacetate methyl ester	Generator
Β-indolylacetate methyl ester	Generator
Β-indolylacetic acid methyl ester	Generator
Indole-3-acetate, methyl ester	Generator
Methyl 3-indolylacetic acid	Generator
Methyl b-indoleacetate	Generator
Methyl b-indoleacetic acid	Generator
Methyl beta-indoleacetic acid	Generator
Methyl β-indoleacetate	Generator
Methyl β-indoleacetic acid	Generator
Methyl b-indolylacetate	Generator
Methyl b-indolylacetic acid	Generator
Methyl beta-indolylacetic acid	Generator
Methyl β-indolylacetate	Generator
Methyl β-indolylacetic acid	Generator
Methyl indol-3-ylacetic acid	Generator
Indole-3-methyl acetic acid	Generator
1H-Indole-3-acetic acid, methyl ester	HMDB
beta -Indolylacetic acid methyl ester	HMDB
IAA methyl ester	HMDB
Indole-3-acetic acid methyl ester	HMDB
INDOLE-3-acetIC ACID methylester	HMDB
Meiaa	HMDB
Methyl 1H-indol-3-ylacetate	HMDB
Methyl 2-(1H-indol-3-yl)acetate	HMDB
Methyl beta -indoleacetate	HMDB
Methyl beta -indolylacetate	HMDB
Methyl iaa	HMDB
Methyl indole-3-acetate	HMDB
Methylester OF 3-indoleacetic acid	HMDB
Methyl (indol-3-yl)acetic acid	Generator
(1H-Indol-3-yl)acetic acid methyl ester	HMDB
Indolyl-3-acetic acid methyl ester	HMDB
Methyl 1H-indole-3-acetate	HMDB
Methyl-IAA	HMDB

Chemical Formula

C₁₁H₁₁NO₂

Average Mass

189.2105 Da

Monoisotopic Mass

189.07898 Da

IUPAC Name

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

Traditional Name

methyl 1H-indol-3-ylacetate

CAS Registry Number

1912-33-0

SMILES

COC(=O)CC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C11H11NO2/c1-14-11(13)6-8-7-12-10-5-3-2-4-9(8)10/h2-5,7,12H,6H2,1H3

InChI Key

KTHADMDGDNYQRX-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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	2024-06-14	View Spectrum
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	2024-06-14	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	2024-06-14	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	2024-06-14	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	2024-06-14	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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	2024-06-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Brassica oleracea	Plant	KNApSAcK
Brassica oleracea var. botrytis	FooDB	KNAPSACK
Castanea crenata	FooDB	KNAPSACK
Chamaecyparis lawsoniana	Plant	KNApSAcK
Citrus reticulata	LOTUS Database	35616633
Citrus unshiu	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	KNAPSACK
Corylus avellana	FooDB	KNAPSACK
Cotinus coggygria	Plant	KNApSAcK
Dalbergia dolichopetala	Plant	KNApSAcK
Diospyros kaki	FooDB	KNAPSACK
Euphorbia escula	Plant	KNApSAcK
Glycine soja	Plant	KNApSAcK
Homo sapiens	Animalia	KNApSAcK
Lablab purpureus	FooDB	KNAPSACK
Lathyrus maritimus	Plant	KNApSAcK
Lygodium flexuosum	Plant	KNApSAcK
Malus pumila	FooDB	KNAPSACK
Nicotiana tabacum	Plant	KNApSAcK
Panax ginseng	Plant	KNApSAcK
Phaseolus vulgaris	FooDB	KNAPSACK
Picea abies	Plant	KNApSAcK
Picea sitchensis	Plant	KNApSAcK
Pinus contorta	Plant	KNApSAcK
Pinus slyvestris	Plant	KNApSAcK
Pisum sativum	FooDB	KNAPSACK
Prunus cerasus	FooDB	KNAPSACK
Prunus domestica	FooDB	KNAPSACK
Pseudomonas amygdali	LOTUS Database	35616633
Pseudomonas savastanoi	LOTUS Database	35616633
Pseudotsuga menziesii	Plant	KNApSAcK
Quercus robur	Plant	KNApSAcK
Raphanus sativus	FooDB	KNAPSACK
Rhizopus oryzae	Fungi	KNApSAcK
Ricinus communis	Plant	KNApSAcK
Saccharomyces cerevisiae	Fungi	KNApSAcK
Solanum lycopersicum	Plant	KNApSAcK
Solanum lycopersicum var. lycopersicum	FooDB	KNAPSACK
Vicia amurensis	Plant	KNApSAcK
Vigna mungo	FooDB	KNAPSACK
Vigna unguiculata var. sesquipedalis	Plant	KNApSAcK
Vitis vinifera L.	FooDB	KNAPSACK
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Methyl ester
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

indoles (CHEBI:72782 )
methyl ester (CHEBI:72782 )
a plant hormone (CPD-10546 )

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	2.61	ALOGPS
logP	1.86	ChemAxon
logS	-2.2	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	3	ChemAxon
Refractivity	53.22 m³·mol⁻¹	ChemAxon
Polarizability	19.78 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