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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:45:27 UTC

Update Date

2023-02-21 17:27:57 UTC

HMDB ID

HMDB0040220

Secondary Accession Numbers

HMDB40220

Metabolite Identification

Common Name

Diethyl L-malate

Description

Diethyl L-malate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Diethyl L-malate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Diethyl L-malate.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.966   1.960   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.990   0.418   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.336  -0.329   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.658   0.467   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.699  -1.914   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.673  -0.372   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.674   0.375   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.995  -0.421   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.967  -1.960   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -3.339   0.326   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.005  -0.277   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.658  -0.467   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.005   0.280   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3   11                                                       
CONECT    5    6                                                            
CONECT    6    2    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   12                                                       
CONECT   11    4                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0040220
HETATM    1  C1  UNL     1       4.812   0.598   0.138  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.012   0.680  -1.141  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.648   0.925  -0.915  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.797   0.133  -0.200  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.263  -0.919   0.310  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.352   0.444   0.007  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.325  -0.620   0.839  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.194  -1.838   0.137  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.780  -0.329   0.899  1.00  0.00           C  
HETATM   10  O4  UNL     1      -2.188   0.720   1.480  1.00  0.00           O  
HETATM   11  O5  UNL     1      -2.740  -1.148   0.348  1.00  0.00           O  
HETATM   12  C7  UNL     1      -4.117  -0.903   0.388  1.00  0.00           C  
HETATM   13  C8  UNL     1      -4.508   0.396  -0.281  1.00  0.00           C  
HETATM   14  H1  UNL     1       5.106  -0.458   0.338  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.261   0.989   1.017  1.00  0.00           H  
HETATM   16  H3  UNL     1       5.755   1.198  -0.014  1.00  0.00           H  
HETATM   17  H4  UNL     1       4.216  -0.231  -1.722  1.00  0.00           H  
HETATM   18  H5  UNL     1       4.381   1.539  -1.776  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.210   1.449   0.452  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.103   0.471  -1.004  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.118  -0.745   1.825  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.801  -1.848  -0.647  1.00  0.00           H  
HETATM   23  H10 UNL     1      -4.618  -1.726  -0.179  1.00  0.00           H  
HETATM   24  H11 UNL     1      -4.542  -0.913   1.400  1.00  0.00           H  
HETATM   25  H12 UNL     1      -5.632   0.421  -0.270  1.00  0.00           H  
HETATM   26  H13 UNL     1      -4.217   0.438  -1.337  1.00  0.00           H  
HETATM   27  H14 UNL     1      -4.167   1.276   0.297  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   19   20
CONECT    7    8    9   21
CONECT    8   22
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   23   24
CONECT   13   25   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Diethyl L-malic acid	Generator
Butanedioic acid, 2-hydroxy-, 1,4-diethyl ester	HMDB
Butanedioic acid, hydroxy-, diethyl ester	HMDB
Diethyl (1)-malate	HMDB
Diethyl hydroxybutanedioate	HMDB
Diethyl hydroxybutanoate	HMDB
Diethyl malate	HMDB
Ethyl DL-malate	HMDB
Ethyl malate	HMDB
Ethyl-DL-malate	HMDB
Hydroxy-diethyl ester(.+/-.)-butanedioic acid	HMDB
L-(-)-Malic acid diethyl ester	HMDB
Malic acid, diethyl ester	HMDB
Diethyl malate, (R)-isomer	MeSH, HMDB
Diethyl malate, (+-)-isomer	MeSH, HMDB
Diethyl malate, (S)-isomer	MeSH, HMDB
Diethyl malic acid	Generator
Diethyl D-malic acid	Generator

Chemical Formula

C₈H₁₄O₅

Average Molecular Weight

190.1938

Monoisotopic Molecular Weight

190.084123558

IUPAC Name

1,4-diethyl 2-hydroxybutanedioate

Traditional Name

1,4-diethyl 2-hydroxybutanedioate

CAS Registry Number

7554-28-1

SMILES

CCOC(=O)CC(O)C(=O)OCC

InChI Identifier

InChI=1S/C8H14O5/c1-3-12-7(10)5-6(9)8(11)13-4-2/h6,9H,3-5H2,1-2H3

InChI Key

VKNUORWMCINMRB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

malate ester (CHEBI:87368 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040220)
Cytoplasm (HMDB: HMDB0040220)

Source

Exogenous

Exogenous (HMDB: HMDB0040220)

Food

Fruit

Fruits (FooDB: FOOD00871)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

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
Water Solubility	96.5 g/L	ALOGPS
logP	0.34	ALOGPS
logP	-0.11	ChemAxon
logS	-0.29	ALOGPS
pKa (Strongest Acidic)	12.44	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	43.91 m³·mol⁻¹	ChemAxon
Polarizability	18.75 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]+	143.56	31661259
DarkChem	[M-H]-	141.668	31661259
DeepCCS	[M+H]+	141.901	30932474
DeepCCS	[M-H]-	139.181	30932474
DeepCCS	[M-2H]-	175.544	30932474
DeepCCS	[M+Na]+	150.843	30932474
AllCCS	[M+H]+	144.8	32859911
AllCCS	[M+H-H2O]+	141.1	32859911
AllCCS	[M+NH4]+	148.2	32859911
AllCCS	[M+Na]+	149.2	32859911
AllCCS	[M-H]-	142.9	32859911
AllCCS	[M+Na-2H]-	144.4	32859911
AllCCS	[M+HCOO]-	146.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diethyl L-malate	CCOC(=O)CC(O)C(=O)OCC	2317.9	Standard polar	33892256
Diethyl L-malate	CCOC(=O)CC(O)C(=O)OCC	1182.5	Standard non polar	33892256
Diethyl L-malate	CCOC(=O)CC(O)C(=O)OCC	1331.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diethyl L-malate,1TMS,isomer #1	CCOC(=O)CC(O[Si](C)(C)C)C(=O)OCC	1386.6	Semi standard non polar	33892256
Diethyl L-malate,1TBDMS,isomer #1	CCOC(=O)CC(O[Si](C)(C)C(C)(C)C)C(=O)OCC	1594.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Diethyl L-malate EI-B (Non-derivatized)	splash10-00vl-9200000000-0e2b63fa1358ecc4727d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diethyl L-malate EI-B (Non-derivatized)	splash10-00vl-9200000000-0e2b63fa1358ecc4727d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethyl L-malate GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9800000000-c3cb88ecf650c67efe5e	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethyl L-malate GC-MS (1 TMS) - 70eV, Positive	splash10-0079-8920000000-732bc15836f011a383a3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethyl L-malate 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 - Diethyl L-malate 10V, Positive-QTOF	splash10-0007-1900000000-815e69499173edb4db80	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl L-malate 20V, Positive-QTOF	splash10-000b-9800000000-b787dba980fd1db16e61	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl L-malate 40V, Positive-QTOF	splash10-0002-9200000000-4e46a07b9fd73378c9ca	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl L-malate 10V, Negative-QTOF	splash10-000l-3900000000-f255ae39fead1d6d56dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl L-malate 20V, Negative-QTOF	splash10-0075-9800000000-916e9fe90e1aecbe634d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl L-malate 40V, Negative-QTOF	splash10-00dv-9100000000-c36e5fae8fc58b06cf20	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl L-malate 10V, Negative-QTOF	splash10-0079-3900000000-349bf26b0d73cd973a8c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl L-malate 20V, Negative-QTOF	splash10-00fv-9400000000-2464ee9878c2e2c698a0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl L-malate 40V, Negative-QTOF	splash10-0076-9000000000-888ebde00273a66ebeb0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl L-malate 10V, Positive-QTOF	splash10-00kb-3900000000-8c2cbe244fa84072171c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl L-malate 20V, Positive-QTOF	splash10-0fxt-8900000000-7b232d5d7b06aaf439bb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethyl L-malate 40V, Positive-QTOF	splash10-006w-9100000000-a25e4bfa8d5a0b9203da	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

FDB019933

KNApSAcK ID

Not Available

Chemspider ID

22619

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24197

PDB ID

Not Available

ChEBI ID

87368

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Diethyl L-malate (HMDB0040220)

MOL for HMDB0040220 (Diethyl L-malate)

3D MOL for HMDB0040220 (Diethyl L-malate)

3D SDF for HMDB0040220 (Diethyl L-malate)

3D-SDF for HMDB0040220 (Diethyl L-malate)

PDB for HMDB0040220 (Diethyl L-malate)

3D PDB for HMDB0040220 (Diethyl L-malate)

SMILES for HMDB0040220 (Diethyl L-malate)

INCHI for HMDB0040220 (Diethyl L-malate)

Structure for HMDB0040220 (Diethyl L-malate)

3D Structure for HMDB0040220 (Diethyl L-malate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra