Showing Compound (R)-2-Benzylsuccinate (FDB028791)

Record Information

Version

1.0

Creation date

2011-09-21 01:45:00 UTC

Update date

2015-10-09 22:33:28 UTC

Primary ID

FDB028791

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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). [HMDB]

CAS Number

884-33-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(R)-2-Benzylsuccinic acid	Generator
(2R)-2-Benzylsuccinic acid	HMDB
L-Benzylsuccinate	HMDB
L-Benzylsuccinic acid	HMDB
(2S)-2-Benzylbutanedioate	Generator, HMDB
(2R)-2-benzylsuccinic acid	hmdb
L-benzylsuccinate	hmdb
L-benzylsuccinic acid	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	1.47 g/L	ALOGPS
logP	1.43	ALOGPS
logP	1.72	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	52.81 m³·mol⁻¹	ChemAxon
Polarizability	20.52 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

Chemical Formula

C11H12O4

IUPAC name

(2S)-2-benzylbutanedioic acid

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 Key

GTOFKXZQQDSVFH-VIFPVBQESA-N

Isomeric SMILES

OC(=O)C[C@H](CC1=CC=CC=C1)C(O)=O

Average Molecular Weight

208.2106

Monoisotopic Molecular Weight

208.073558872

Classification

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(R)-2-Benzylsuccinate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9800000000-5de889b4c36c3e909843	Spectrum
Predicted GC-MS	(R)-2-Benzylsuccinate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-007c-9070000000-019dc31183f7029405a8	Spectrum
Predicted GC-MS	(R)-2-Benzylsuccinate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00dl-0900000000-86ec9667b560cf42409b	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00r2-0900000000-3a815068b069da997597	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-0900000000-a16a7c749686cfa3f5dd	2012-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0910000000-5a8ce5a01560eabb3ae5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01oy-2900000000-b460fa93b6e2cb36e1f5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-6900000000-55695b21ccd9fb29115f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-0960000000-abc21e2625fb843cc09b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fr-0910000000-ce726630b288b3ea18d6	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9300000000-76dcdd6634fa068b0445	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0910000000-fb9f22c71853f063789d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-4900000000-f860244be1113634b924	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-5ae6060973c140f65661	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0005-0900000000-3d9a6f96e17b84f86a32	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014l-5900000000-df2b9f60ea02e875fd89	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-7900000000-198aef11b236da952965	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 500 MHz, H₂O, experimental)		Spectrum