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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-10-01 18:05:29 UTC

Update Date

2021-10-01 18:05:29 UTC

HMDB ID

HMDB0304946

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Indole-3-acetic acid ethyl ester

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 3D MOL SDF 3D SDF PDB 3D 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>
HMDB0304946

> <DATABASE_NAME>
hmdb

> <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

COMPND    HMDB0304946
HETATM    1  C1  UNL     1       3.379   1.360  -0.189  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.321   0.691   1.174  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.110  -0.054   1.347  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.745  -1.025   0.432  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.568  -1.168  -0.562  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.566  -1.884   0.447  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.544  -1.441  -0.416  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.975  -1.847  -1.646  1.00  0.00           C  
HETATM    9  N1  UNL     1      -2.057  -1.096  -2.027  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.333  -0.209  -1.050  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.319   0.775  -0.922  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.391   1.566   0.207  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.458   1.352   1.195  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.475   0.390   1.089  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.414  -0.399  -0.044  1.00  0.00           C  
HETATM   16  H1  UNL     1       3.815   2.370  -0.114  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.347   1.452  -0.562  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.060   0.787  -0.876  1.00  0.00           H  
HETATM   19  H4  UNL     1       4.220   0.161   1.472  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.220   1.542   1.928  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.919  -2.917   0.161  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.236  -2.020   1.518  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.533  -2.635  -2.215  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.562  -1.207  -2.913  1.00  0.00           H  
HETATM   25  H10 UNL     1      -4.052   0.948  -1.699  1.00  0.00           H  
HETATM   26  H11 UNL     1      -4.167   2.303   0.282  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.499   1.968   2.105  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.727   0.236   1.878  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   21   22
CONECT    7    8    8   15
CONECT    8    9   23
CONECT    9   10   24
CONECT   10   11   11   15
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   14   27
CONECT   14   15   15   28
END

View in JSmol View Stereo Labels

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 Molecular Weight

203.2371

Monoisotopic Molecular Weight

203.094628665

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

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

Ontology

Not Available

Not Available

Not Available

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	3.04	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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	144.831	32859911
AllCCS	[M+H-H2O]+	140.691	32859911
AllCCS	[M+Na]+	149.795	32859911
AllCCS	[M+NH4]+	148.685	32859911
AllCCS	[M-H]-	148.714	32859911
AllCCS	[M+Na-2H]-	148.835	32859911
AllCCS	[M+HCOO]-	149.063	32859911
DeepCCS	[M-2H]-	177.188	30932474
DeepCCS	[M+Na]+	152.726	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	13.8562 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.72 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2153.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	450.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	160.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	248.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	328.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	559.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	539.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	133.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1167.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	448.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1429.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	452.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	379.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	348.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	415.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	49.0 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-acetic acid ethyl ester,1TMS,isomer #1	CCOC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	1919.7	Semi standard non polar	33892256
Indole-3-acetic acid ethyl ester,1TMS,isomer #1	CCOC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	1876.5	Standard non polar	33892256
Indole-3-acetic acid ethyl ester,1TMS,isomer #1	CCOC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2303.7	Standard polar	33892256
Indole-3-acetic acid ethyl ester,1TBDMS,isomer #1	CCOC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2148.2	Semi standard non polar	33892256
Indole-3-acetic acid ethyl ester,1TBDMS,isomer #1	CCOC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2087.5	Standard non polar	33892256
Indole-3-acetic acid ethyl ester,1TBDMS,isomer #1	CCOC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2413.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Indole-3-acetic acid ethyl ester GC-MS (1 TMS)	splash10-0udi-0190000000-9ff7f511234eecd992ad	2014-06-16	HMDB team, MONA, MassBank	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic acid ethyl ester 10V, Positive-QTOF	splash10-001i-0910000000-13351c26b7a034511c82	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic acid ethyl ester 20V, Positive-QTOF	splash10-053r-0910000000-a888639e608fd01985c0	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic acid ethyl ester 40V, Positive-QTOF	splash10-001i-4900000000-51fc457668a013d5f145	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic acid ethyl ester 10V, Negative-QTOF	splash10-0a4i-1920000000-05ad9a381447428a0a59	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic acid ethyl ester 20V, Negative-QTOF	splash10-0560-0900000000-e4b5c541ac380f91db35	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic acid ethyl ester 40V, Negative-QTOF	splash10-004i-0900000000-d795bf47b023cf7eb8fc	2021-10-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

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

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

National Institute of Environmental Health Science (NIEHS) [Link]

Showing metabocard for Indole-3-acetic acid ethyl ester (HMDB0304946)

MOL for HMDB0304946 (Indole-3-acetic acid ethyl ester)

3D MOL for HMDB0304946 (Indole-3-acetic acid ethyl ester)

3D SDF for HMDB0304946 (Indole-3-acetic acid ethyl ester)

3D-SDF for HMDB0304946 (Indole-3-acetic acid ethyl ester)

PDB for HMDB0304946 (Indole-3-acetic acid ethyl ester)

3D PDB for HMDB0304946 (Indole-3-acetic acid ethyl ester)

SMILES for HMDB0304946 (Indole-3-acetic acid ethyl ester)

INCHI for HMDB0304946 (Indole-3-acetic acid ethyl ester)

Structure for HMDB0304946 (Indole-3-acetic acid ethyl ester)

3D Structure for HMDB0304946 (Indole-3-acetic acid ethyl ester)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra