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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:48:33 UTC

Update Date

2023-02-21 17:28:06 UTC

HMDB ID

HMDB0040275

Secondary Accession Numbers

HMDB40275

Metabolite Identification

Common Name

Ethyl aconitate

Description

Ethyl aconitate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Ethyl aconitate is a sweet, fruity, and wine tasting compound. Based on a literature review very few articles have been published on Ethyl aconitate.

Structure

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

  Mrv0541 05061311432D          

 14 13  0  0  0  0            999 V2000
   -3.4618    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040275

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)\C=C(\CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O6/c1-2-14-7(11)4-5(8(12)13)3-6(9)10/h4H,2-3H2,1H3,(H,9,10)(H,12,13)/b5-4-

> <INCHI_KEY>
ANIDMCPGEUWERH-PLNGDYQASA-N

> <FORMULA>
C8H10O6

> <MOLECULAR_WEIGHT>
202.1614

> <EXACT_MASS>
202.047738052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
18.03149981042333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-(2-ethoxy-2-oxoethylidene)butanedioic acid

> <ALOGPS_LOGP>
0.32

> <JCHEM_LOGP>
0.21499840200000003

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.018246484473987

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.716909980777201

> <JCHEM_PKA_STRONGEST_BASIC>
-6.84931821562953

> <JCHEM_POLAR_SURFACE_AREA>
100.90000000000002

> <JCHEM_REFRACTIVITY>
44.748200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-2-(2-ethoxy-2-oxoethylidene)butanedioic acid

> <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      -6.462   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.128   0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.795   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.461   0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.461   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.874   2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.207   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.206   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.540   3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.127   3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyl aconitic acid	Generator
Ethyl aconitate (mixed esters)	HMDB
FEMA 2417	HMDB
(2Z)-2-(2-Ethoxy-2-oxoethylidene)butanedioate	Generator

Chemical Formula

C₈H₁₀O₆

Average Molecular Weight

202.1614

Monoisotopic Molecular Weight

202.047738052

IUPAC Name

(2Z)-2-(2-ethoxy-2-oxoethylidene)butanedioic acid

Traditional Name

(2Z)-2-(2-ethoxy-2-oxoethylidene)butanedioic acid

CAS Registry Number

1321-30-8

SMILES

CCOC(=O)\C=C(\CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C8H10O6/c1-2-14-7(11)4-5(8(12)13)3-6(9)10/h4H,2-3H2,1H3,(H,9,10)(H,12,13)/b5-4-

InChI Key

ANIDMCPGEUWERH-PLNGDYQASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040275)
Cytoplasm (HMDB: HMDB0040275)

Source

Exogenous

Exogenous (HMDB: HMDB0040275)

Food

Food (HMDB: HMDB0040275)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040275)

Biological role

Nutrient (HMDB: HMDB0040275)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	260 °C	Not Available
Boiling Point	172.00 °C. @ 18.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	0.508 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.2 g/L	ALOGPS
logP	0.32	ALOGPS
logP	0.21	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	44.75 m³·mol⁻¹	ChemAxon
Polarizability	18.03 Å³	ChemAxon
Number of Rings	0	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]+	146.775	31661259
DarkChem	[M-H]-	141.861	31661259
DeepCCS	[M+H]+	139.741	30932474
DeepCCS	[M-H]-	136.124	30932474
DeepCCS	[M-2H]-	172.953	30932474
DeepCCS	[M+Na]+	148.492	30932474
AllCCS	[M+H]+	144.9	32859911
AllCCS	[M+H-H2O]+	141.2	32859911
AllCCS	[M+NH4]+	148.3	32859911
AllCCS	[M+Na]+	149.3	32859911
AllCCS	[M-H]-	141.0	32859911
AllCCS	[M+Na-2H]-	142.1	32859911
AllCCS	[M+HCOO]-	143.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl aconitate	CCOC(=O)\C=C(\CC(O)=O)C(O)=O	2865.6	Standard polar	33892256
Ethyl aconitate	CCOC(=O)\C=C(\CC(O)=O)C(O)=O	1480.1	Standard non polar	33892256
Ethyl aconitate	CCOC(=O)\C=C(\CC(O)=O)C(O)=O	1737.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl aconitate,1TMS,isomer #1	CCOC(=O)/C=C(/CC(=O)O[Si](C)(C)C)C(=O)O	1749.5	Semi standard non polar	33892256
Ethyl aconitate,1TMS,isomer #2	CCOC(=O)/C=C(/CC(=O)O)C(=O)O[Si](C)(C)C	1674.2	Semi standard non polar	33892256
Ethyl aconitate,2TMS,isomer #1	CCOC(=O)/C=C(/CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1709.6	Semi standard non polar	33892256
Ethyl aconitate,1TBDMS,isomer #1	CCOC(=O)/C=C(/CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1993.4	Semi standard non polar	33892256
Ethyl aconitate,1TBDMS,isomer #2	CCOC(=O)/C=C(/CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1912.0	Semi standard non polar	33892256
Ethyl aconitate,2TBDMS,isomer #1	CCOC(=O)/C=C(/CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2167.4	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 - Ethyl aconitate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-3900000000-7e654bb7050ae29547df	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl aconitate GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-9282000000-c166b7f232a6ba7ab0a2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl aconitate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl aconitate 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 - Ethyl aconitate 10V, Positive-QTOF	splash10-000i-1910000000-195d24f5c981db9efa4d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl aconitate 20V, Positive-QTOF	splash10-06rj-5900000000-74cc6adec17e051ea6e4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl aconitate 40V, Positive-QTOF	splash10-03ei-9400000000-e2eb7889146f0aff81f7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl aconitate 10V, Negative-QTOF	splash10-0zfr-1930000000-c9f12101a8da312d7948	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl aconitate 20V, Negative-QTOF	splash10-114s-2900000000-702c812ae91d85791ffd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl aconitate 40V, Negative-QTOF	splash10-06tp-9300000000-270d9247d6517a444efa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl aconitate 10V, Negative-QTOF	splash10-000i-8910000000-e837c6099ec0ec605565	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl aconitate 20V, Negative-QTOF	splash10-03dr-4900000000-0dde053101dd1cea607f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl aconitate 40V, Negative-QTOF	splash10-01rf-9600000000-7b57ca11efbc51630b59	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl aconitate 10V, Positive-QTOF	splash10-052r-0900000000-9d40f3f273b40784520c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl aconitate 20V, Positive-QTOF	splash10-03dr-3900000000-4fd56a588b03a87c181f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl aconitate 40V, Positive-QTOF	splash10-006y-9100000000-ed319c6e53bbc3022b87	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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+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

FDB019994

KNApSAcK ID

Not Available

Chemspider ID

30777482

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25088425

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1022261

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 Ethyl aconitate (HMDB0040275)

MOL for HMDB0040275 (Ethyl aconitate)

3D MOL for HMDB0040275 (Ethyl aconitate)

3D SDF for HMDB0040275 (Ethyl aconitate)

3D-SDF for HMDB0040275 (Ethyl aconitate)

PDB for HMDB0040275 (Ethyl aconitate)

3D PDB for HMDB0040275 (Ethyl aconitate)

SMILES for HMDB0040275 (Ethyl aconitate)

INCHI for HMDB0040275 (Ethyl aconitate)

Structure for HMDB0040275 (Ethyl aconitate)

3D Structure for HMDB0040275 (Ethyl aconitate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra