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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:58:34 UTC

Update Date

2022-03-07 02:56:13 UTC

HMDB ID

HMDB0039494

Secondary Accession Numbers

HMDB39494

Metabolite Identification

Common Name

Benzoylmalic acid

Description

Benzoylmalic acid, also known as benzoylmalate, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Benzoylmalic acid has been detected, but not quantified in, pulses. This could make benzoylmalic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Benzoylmalic acid.

Structure

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


  Mrv0541 05061311112D          

 17 17  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 16 11  2  0  0  0  0
 17  8  1  0  0  0  0
 17 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039494

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC(OC(=O)C1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O6/c12-9(13)6-8(10(14)15)17-11(16)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,12,13)(H,14,15)

> <INCHI_KEY>
NVPJTXMOQCANSN-UHFFFAOYSA-N

> <FORMULA>
C11H10O6

> <MOLECULAR_WEIGHT>
238.1935

> <EXACT_MASS>
238.047738052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
21.705910159912538

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(benzoyloxy)butanedioic acid

> <ALOGPS_LOGP>
0.83

> <JCHEM_LOGP>
1.3816584206666667

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.01389530348659

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.159810086210867

> <JCHEM_PKA_STRONGEST_BASIC>
-6.920356716732879

> <JCHEM_POLAR_SURFACE_AREA>
100.89999999999999

> <JCHEM_REFRACTIVITY>
54.69720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(benzoyloxy)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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    7                                                       
CONECT    6    8    9                                                       
CONECT    7    4    5   11                                                  
CONECT    8    6   10   17                                                  
CONECT    9    6   12   13                                                  
CONECT   10    8   14   15                                                  
CONECT   11    7   16   17                                                  
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15   10                                                            
CONECT   16   11                                                            
CONECT   17    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0039494
HETATM    1  O1  UNL     1       4.199  -0.050   1.634  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.003   0.522   0.546  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.084   1.161  -0.043  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.692   0.533  -0.105  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.691  -0.321   0.624  1.00  0.00           C  
HETATM    6  O3  UNL     1       0.410  -0.230  -0.052  1.00  0.00           O  
HETATM    7  C4  UNL     1      -0.688   0.143   0.692  1.00  0.00           C  
HETATM    8  O4  UNL     1      -0.511   0.382   1.913  1.00  0.00           O  
HETATM    9  C5  UNL     1      -2.032   0.266   0.105  1.00  0.00           C  
HETATM   10  C6  UNL     1      -3.088   0.640   0.903  1.00  0.00           C  
HETATM   11  C7  UNL     1      -4.357   0.763   0.372  1.00  0.00           C  
HETATM   12  C8  UNL     1      -4.583   0.509  -0.982  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.514   0.138  -1.751  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.265   0.018  -1.228  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.066  -1.752   0.490  1.00  0.00           C  
HETATM   16  O5  UNL     1       1.266  -2.517  -0.153  1.00  0.00           O  
HETATM   17  O6  UNL     1       3.224  -2.298   1.019  1.00  0.00           O  
HETATM   18  H1  UNL     1       5.343   1.044  -0.999  1.00  0.00           H  
HETATM   19  H2  UNL     1       2.788   0.243  -1.173  1.00  0.00           H  
HETATM   20  H3  UNL     1       2.272   1.581  -0.076  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.598  -0.064   1.677  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.946   0.847   1.967  1.00  0.00           H  
HETATM   23  H6  UNL     1      -5.218   1.054   0.956  1.00  0.00           H  
HETATM   24  H7  UNL     1      -5.562   0.597  -1.418  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.644  -0.069  -2.809  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.398  -0.282  -1.847  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.168  -2.859   1.866  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   18
CONECT    4    5   19   20
CONECT    5    6   15   21
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   14
CONECT   10   11   22
CONECT   11   12   12   23
CONECT   12   13   24
CONECT   13   14   14   25
CONECT   14   26
CONECT   15   16   16   17
CONECT   17   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Benzoylmalate	Generator
2-(Benzoyloxy)butanedioate	Generator
L-Malate benzoate	Generator
L-Malic acid benzoic acid	Generator

Chemical Formula

C₁₁H₁₀O₆

Average Molecular Weight

238.1935

Monoisotopic Molecular Weight

238.047738052

IUPAC Name

2-(benzoyloxy)butanedioic acid

Traditional Name

2-(benzoyloxy)butanedioic acid

CAS Registry Number

22138-51-8

SMILES

OC(=O)CC(OC(=O)C1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C11H10O6/c12-9(13)6-8(10(14)15)17-11(16)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,12,13)(H,14,15)

InChI Key

NVPJTXMOQCANSN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Tricarboxylic acid or derivatives
Benzoyl
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039494)
Cytoplasm (HMDB: HMDB0039494)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039494)

Source

Exogenous

Food

Food (HMDB: HMDB0039494)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Fabaceae (HMDB: HMDB0039494)

Not Available

Nutrient (HMDB: HMDB0039494)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	142 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3125 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.7 g/L	ALOGPS
logP	0.83	ALOGPS
logP	1.38	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	-6.9	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	54.7 m³·mol⁻¹	ChemAxon
Polarizability	21.71 Å³	ChemAxon
Number of Rings	1	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]+	155.157	31661259
DarkChem	[M-H]-	151.681	31661259
DeepCCS	[M+H]+	146.08	30932474
DeepCCS	[M-H]-	143.722	30932474
DeepCCS	[M-2H]-	177.719	30932474
DeepCCS	[M+Na]+	152.999	30932474
AllCCS	[M+H]+	151.6	32859911
AllCCS	[M+H-H2O]+	148.0	32859911
AllCCS	[M+NH4]+	155.0	32859911
AllCCS	[M+Na]+	156.0	32859911
AllCCS	[M-H]-	150.1	32859911
AllCCS	[M+Na-2H]-	150.2	32859911
AllCCS	[M+HCOO]-	150.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzoylmalic acid	OC(=O)CC(OC(=O)C1=CC=CC=C1)C(O)=O	3373.5	Standard polar	33892256
Benzoylmalic acid	OC(=O)CC(OC(=O)C1=CC=CC=C1)C(O)=O	1889.9	Standard non polar	33892256
Benzoylmalic acid	OC(=O)CC(OC(=O)C1=CC=CC=C1)C(O)=O	2007.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzoylmalic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC(OC(=O)C1=CC=CC=C1)C(=O)O	2005.2	Semi standard non polar	33892256
Benzoylmalic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(CC(=O)O)OC(=O)C1=CC=CC=C1	1997.3	Semi standard non polar	33892256
Benzoylmalic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC(OC(=O)C1=CC=CC=C1)C(=O)O[Si](C)(C)C	2006.7	Semi standard non polar	33892256
Benzoylmalic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(OC(=O)C1=CC=CC=C1)C(=O)O	2257.9	Semi standard non polar	33892256
Benzoylmalic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(CC(=O)O)OC(=O)C1=CC=CC=C1	2229.4	Semi standard non polar	33892256
Benzoylmalic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(OC(=O)C1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2461.4	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 - Benzoylmalic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1900000000-7fe8bcdbe6fbc86b6e9a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoylmalic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-4921000000-a8b804d7ec7c1bc6d3a1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoylmalic acid 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 - Benzoylmalic acid 10V, Positive-QTOF	splash10-00dr-1690000000-71e5af1a1985beb3c0b4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylmalic acid 20V, Positive-QTOF	splash10-0ab9-2930000000-e8eb5899472d07693365	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylmalic acid 40V, Positive-QTOF	splash10-0a4i-7900000000-7a5c44517647e1b217c3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylmalic acid 10V, Negative-QTOF	splash10-00rl-1940000000-9af14abecbc486d9c7c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylmalic acid 20V, Negative-QTOF	splash10-00di-3900000000-e27675f819109dc8d985	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylmalic acid 40V, Negative-QTOF	splash10-00b9-9600000000-1ff83ac7b3ba338a63fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylmalic acid 10V, Negative-QTOF	splash10-00dr-9600000000-7c40801cbcebdb17664e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylmalic acid 20V, Negative-QTOF	splash10-00fr-9300000000-6fc337fa10a23f01eb28	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylmalic acid 40V, Negative-QTOF	splash10-00b9-9000000000-d83c7ed96fd3e423a182	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylmalic acid 10V, Positive-QTOF	splash10-0a4i-0910000000-11aa4acb894c2c49dfb4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylmalic acid 20V, Positive-QTOF	splash10-0a6r-5900000000-8fe9184b96e821d21e22	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoylmalic acid 40V, Positive-QTOF	splash10-0a4i-4900000000-df52d0c219d5b5739d1f	2021-09-25	Wishart 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

FDB019101

KNApSAcK ID

C00054031

Chemspider ID

35014810

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13953341

PDB ID

Not Available

ChEBI ID

174225

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1877751

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 Benzoylmalic acid (HMDB0039494)

MOL for HMDB0039494 (Benzoylmalic acid)

3D MOL for HMDB0039494 (Benzoylmalic acid)

3D SDF for HMDB0039494 (Benzoylmalic acid)

3D-SDF for HMDB0039494 (Benzoylmalic acid)

PDB for HMDB0039494 (Benzoylmalic acid)

3D PDB for HMDB0039494 (Benzoylmalic acid)

SMILES for HMDB0039494 (Benzoylmalic acid)

INCHI for HMDB0039494 (Benzoylmalic acid)

Structure for HMDB0039494 (Benzoylmalic acid)

3D Structure for HMDB0039494 (Benzoylmalic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra