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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 07:04:08 UTC

Update Date

2021-09-24 07:04:08 UTC

HMDB ID

HMDB0304087

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-succinylbenzoate

Description

O-succinylbenzoate, also known as 4-(2'-carboxyphenyl)-4-oxobutyric acid or 2-(3-carboxypropionyl)benzoic acid, is a member of the class of compounds known as alkyl-phenylketones. Alkyl-phenylketones are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. O-succinylbenzoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). O-succinylbenzoate can be synthesized from benzoic acid. O-succinylbenzoate can also be synthesized into 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA. O-succinylbenzoate can be found in a number of food items such as nectarine, green bean, japanese persimmon, and rye, which makes O-succinylbenzoate a potential biomarker for the consumption of these food products. O-succinylbenzoate may be a unique E.coli metabolite.

Structure

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

OSB
  Mrv0541 02231216042D          

 16 16  0  0  0  0            999 V2000
   -1.7771    1.6116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3481    1.6116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0626    1.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3481   -0.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0626   -1.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771   -0.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771   -0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0626    0.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3481   -0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3663    0.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0808   -0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3663    1.1991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7953    0.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5098   -0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2242    0.3741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5098   -0.8634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  3  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304087

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O5/c12-9(5-6-10(13)14)7-3-1-2-4-8(7)11(15)16/h1-4H,5-6H2,(H,13,14)(H,15,16)

> <INCHI_KEY>
YIVWQNVQRXFZJB-UHFFFAOYSA-N

> <FORMULA>
C11H10O5

> <MOLECULAR_WEIGHT>
222.1941

> <EXACT_MASS>
222.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
21.23485677124057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-carboxypropanoyl)benzoic acid

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
1.0133389896666665

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.595760241001752

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.418431058331099

> <JCHEM_PKA_STRONGEST_BASIC>
-7.57018002288234

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
54.61030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-succinylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: OSB                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      -3.317   3.008   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -0.650   3.008   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.984   2.238   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.650  -1.612   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.984  -2.382   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.317  -1.612   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.317  -0.072   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.984   0.698   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.650  -0.072   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.684   0.698   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.017  -0.072   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.684   2.238   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.351   0.698   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.685  -0.072   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.019   0.698   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.685  -1.612   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    3                                                            
CONECT    3    1    2    8                                                  
CONECT    4    5    9                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    4    8   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0304087
HETATM    1  O1  UNL     1       2.709  -0.431  -1.438  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.410  -0.227  -0.440  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.731   0.200  -0.616  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.912  -0.414   0.948  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.468  -0.839   0.923  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.634   0.240   0.264  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.259   1.243  -0.082  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.777  -0.064   0.136  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.272  -1.288   0.613  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.592  -1.618   0.516  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.492  -0.757  -0.056  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.012   0.436  -0.521  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.655   0.812  -0.439  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.304   2.111  -0.979  1.00  0.00           C  
HETATM   15  O4  UNL     1      -0.190   2.635  -1.013  1.00  0.00           O  
HETATM   16  O5  UNL     1      -2.322   2.902  -1.540  1.00  0.00           O  
HETATM   17  H1  UNL     1       5.443  -0.432  -0.246  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.536  -1.163   1.470  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.984   0.583   1.480  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.308  -1.738   0.304  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.086  -1.004   1.939  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.561  -1.986   1.073  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.948  -2.584   0.900  1.00  0.00           H  
HETATM   24  H8  UNL     1      -4.554  -1.020  -0.135  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.715   1.138  -0.982  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.087   3.265  -1.023  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7    7    8
CONECT    8    9    9   13
CONECT    9   10   22
CONECT   10   11   11   23
CONECT   11   12   24
CONECT   12   13   13   25
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3-Carboxypropionyl)benzoic acid	ChEBI
2-SUCCINYLBENZOATE	ChEBI
4-(2'-Carboxyphenyl)-4-oxobutyric acid	ChEBI
O-Succinylbenzoic acid	ChEBI
Succinylbenzoate	ChEBI
2-(3-Carboxypropionyl)benzoate	Generator
2-SUCCINYLBENZOic acid	Generator
4-(2'-Carboxyphenyl)-4-oxobutyrate	Generator
Succinylbenzoic acid	Generator
O-Succinylbenzoate	ChEBI, KEGG

Chemical Formula

C₁₁H₁₀O₅

Average Molecular Weight

222.1941

Monoisotopic Molecular Weight

222.05282343

IUPAC Name

2-(3-carboxypropanoyl)benzoic acid

Traditional Name

O-succinylbenzoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H10O5/c12-9(5-6-10(13)14)7-3-1-2-4-8(7)11(15)16/h1-4H,5-6H2,(H,13,14)(H,15,16)

InChI Key

YIVWQNVQRXFZJB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Aryl alkyl ketone
Gamma-keto acid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Keto acid
Benzenoid
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:44788 )

Ontology

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	0.87	ALOGPS
logP	1.01	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.42	ChemAxon
pKa (Strongest Basic)	-7.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	54.61 m³·mol⁻¹	ChemAxon
Polarizability	21.23 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
AllCCS	[M+H]+	148.137	32859911
AllCCS	[M+H-H2O]+	144.244	32859911
AllCCS	[M+Na]+	152.798	32859911
AllCCS	[M+NH4]+	151.756	32859911
AllCCS	[M-H]-	146.583	32859911
AllCCS	[M+Na-2H]-	146.813	32859911
AllCCS	[M+HCOO]-	147.163	32859911
DeepCCS	[M+H]+	144.311	30932474
DeepCCS	[M-H]-	141.953	30932474
DeepCCS	[M-2H]-	176.065	30932474
DeepCCS	[M+Na]+	150.784	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.1944 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.65 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1371.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	285.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	110.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	94.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	314.0 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	400.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	758.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	328.8 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	1044.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	244.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	490.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	183.8 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	235.4 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-succinylbenzoate 10V, Positive-QTOF	splash10-0a4i-0590000000-852b41c075a2f3673677	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-succinylbenzoate 20V, Positive-QTOF	splash10-0a4i-1930000000-74242e299c1efe8e7cde	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-succinylbenzoate 40V, Positive-QTOF	splash10-053r-3900000000-8a860f760912ebe7688d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-succinylbenzoate 10V, Negative-QTOF	splash10-00di-0590000000-2029d0b8fdb139223f02	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-succinylbenzoate 20V, Negative-QTOF	splash10-0kk9-0940000000-25652eda070ac9fee146	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-succinylbenzoate 40V, Negative-QTOF	splash10-0a7i-3910000000-7e5a38de6b3824bb2a46	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-succinylbenzoate 10V, Positive-QTOF	splash10-0a4i-0970000000-c01c8dd3daf408904029	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-succinylbenzoate 20V, Positive-QTOF	splash10-0a5i-1910000000-952ab73fd1c5b9cd4d9e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-succinylbenzoate 40V, Positive-QTOF	splash10-0a4i-2900000000-ec509913282ae0721a9a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-succinylbenzoate 10V, Negative-QTOF	splash10-0a4i-0920000000-180b7cab9d19657ef54f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-succinylbenzoate 20V, Negative-QTOF	splash10-0560-2900000000-2823bb6b38cd51325b24	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-succinylbenzoate 40V, Negative-QTOF	splash10-0059-9700000000-879529211d2d7bab79a5	2021-10-21	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

DB02251

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

955

PDB ID

Not Available

ChEBI ID

44788

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

Not Available

Showing metabocard for 2-succinylbenzoate (HMDB0304087)

MOL for HMDB0304087 (2-succinylbenzoate)

3D MOL for HMDB0304087 (2-succinylbenzoate)

3D SDF for HMDB0304087 (2-succinylbenzoate)

3D-SDF for HMDB0304087 (2-succinylbenzoate)

PDB for HMDB0304087 (2-succinylbenzoate)

3D PDB for HMDB0304087 (2-succinylbenzoate)

SMILES for HMDB0304087 (2-succinylbenzoate)

INCHI for HMDB0304087 (2-succinylbenzoate)

Structure for HMDB0304087 (2-succinylbenzoate)

3D Structure for HMDB0304087 (2-succinylbenzoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra