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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:19:40 UTC
Update Date2023-02-21 17:17:37 UTC
HMDB IDHMDB0012127
Secondary Accession Numbers
  • HMDB12127
Metabolite Identification
Common Name(R)-2-Benzylsuccinate
Description(R)-2-Benzylsuccinate is an aromatic compounds that is an intermediate in Benzoate degradation via CoA ligation. Biodegradation of aromatic compounds is a common process in anoxic environments. The many natural and synthetic aromatic compounds found in the environment are usually degraded by anaerobic microorganisms into only few central intermediates, prior to ring cleavage. Benzoyl-CoA is the most important of these intermediates since a large number of compounds, including chloro-, nitro-, and aminobenzoates, aromatic hydrocarbons, and phenolic compounds, are initially converted to benzoyl-CoA prior to ring reduction and cleavage. (R)-2-Benzylsuccinate can be generated from toluene via the enzyme benzylsuccinate synthase (EC 4.1.99.11). It is then converted to Benzylsuccinyl-CoA via the enzyme benzylsuccinate CoA-transferase BbsE subunit (EC 2.8.3.15).
Structure
Data?1676999857
Synonyms
ValueSource
(R)-2-Benzylsuccinic acidGenerator
(2R)-2-Benzylsuccinic acidHMDB
L-BenzylsuccinateHMDB
L-Benzylsuccinic acidHMDB
(2S)-2-BenzylbutanedioateGenerator, HMDB
Chemical FormulaC11H12O4
Average Molecular Weight208.2106
Monoisotopic Molecular Weight208.073558872
IUPAC Name(2S)-2-benzylbutanedioic acid
Traditional Namel-benzylsuccinic acid
CAS Registry Number884-33-3
SMILES
OC(=O)C[C@H](CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C11H12O4/c12-10(13)7-9(11(14)15)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,12,13)(H,14,15)/t9-/m0/s1
InChI KeyGTOFKXZQQDSVFH-VIFPVBQESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.47 g/LALOGPS
logP1.43ALOGPS
logP1.72ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.25ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity52.81 m³·mol⁻¹ChemAxon
Polarizability20.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.47231661259
DarkChem[M-H]-145.97731661259
DeepCCS[M+H]+142.25830932474
DeepCCS[M-H]-139.86230932474
DeepCCS[M-2H]-173.9130932474
DeepCCS[M+Na]+148.52830932474
AllCCS[M+H]+145.432859911
AllCCS[M+H-H2O]+141.432859911
AllCCS[M+NH4]+149.132859911
AllCCS[M+Na]+150.232859911
AllCCS[M-H]-145.132859911
AllCCS[M+Na-2H]-145.632859911
AllCCS[M+HCOO]-146.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-2-BenzylsuccinateOC(=O)C[C@H](CC1=CC=CC=C1)C(O)=O3209.2Standard polar33892256
(R)-2-BenzylsuccinateOC(=O)C[C@H](CC1=CC=CC=C1)C(O)=O1668.5Standard non polar33892256
(R)-2-BenzylsuccinateOC(=O)C[C@H](CC1=CC=CC=C1)C(O)=O1862.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-2-Benzylsuccinate,1TMS,isomer #1C[Si](C)(C)OC(=O)C[C@H](CC1=CC=CC=C1)C(=O)O1813.8Semi standard non polar33892256
(R)-2-Benzylsuccinate,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CC(=O)O)CC1=CC=CC=C11802.4Semi standard non polar33892256
(R)-2-Benzylsuccinate,2TMS,isomer #1C[Si](C)(C)OC(=O)C[C@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C1848.4Semi standard non polar33892256
(R)-2-Benzylsuccinate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@H](CC1=CC=CC=C1)C(=O)O2059.4Semi standard non polar33892256
(R)-2-Benzylsuccinate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC(=O)O)CC1=CC=CC=C12047.3Semi standard non polar33892256
(R)-2-Benzylsuccinate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C2331.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-2-Benzylsuccinate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9800000000-5de889b4c36c3e9098432017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-2-Benzylsuccinate GC-MS (2 TMS) - 70eV, Positivesplash10-007c-9070000000-019dc31183f7029405a82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-2-Benzylsuccinate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-2-Benzylsuccinate Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00dl-0900000000-86ec9667b560cf42409b2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-2-Benzylsuccinate Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00r2-0900000000-3a815068b069da9975972012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-2-Benzylsuccinate Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014i-0900000000-a16a7c749686cfa3f5dd2012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2-Benzylsuccinate 10V, Positive-QTOFsplash10-0006-0910000000-5a8ce5a01560eabb3ae52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2-Benzylsuccinate 20V, Positive-QTOFsplash10-01oy-2900000000-b460fa93b6e2cb36e1f52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2-Benzylsuccinate 40V, Positive-QTOFsplash10-014l-6900000000-55695b21ccd9fb29115f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2-Benzylsuccinate 10V, Negative-QTOFsplash10-0bt9-0960000000-abc21e2625fb843cc09b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2-Benzylsuccinate 20V, Negative-QTOFsplash10-08fr-0910000000-ce726630b288b3ea18d62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2-Benzylsuccinate 40V, Negative-QTOFsplash10-0a4l-9300000000-76dcdd6634fa068b04452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2-Benzylsuccinate 10V, Negative-QTOFsplash10-03di-0910000000-fb9f22c71853f063789d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2-Benzylsuccinate 20V, Negative-QTOFsplash10-014i-4900000000-f860244be1113634b9242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2-Benzylsuccinate 40V, Negative-QTOFsplash10-0006-9200000000-5ae6060973c140f656612021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2-Benzylsuccinate 10V, Positive-QTOFsplash10-0005-0900000000-3d9a6f96e17b84f86a322021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2-Benzylsuccinate 20V, Positive-QTOFsplash10-014l-5900000000-df2b9f60ea02e875fd892021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-2-Benzylsuccinate 40V, Positive-QTOFsplash10-014l-7900000000-198aef11b236da9529652021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028791
KNApSAcK IDNot Available
Chemspider ID393600
KEGG Compound IDC09816
BioCyc IDBENZYLSUCCINATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound446168
PDB IDNot Available
ChEBI ID1220624
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available