MiMeDB: Showing metabocard for 2-Succinylbenzoate (MMDBc0029982)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:49:20 UTC

Update Date

2022-08-31 17:38:19 UTC

Metabolite ID

MMDBc0029982

Metabolite Identification

Common Name

2-Succinylbenzoate

Description

2-succinylbenzoate is a member of the chemical class known as Benzoic Acid and Derivatives. These are organic compounds containing a carboxylic acid substituent attached to a benzene ring. 2-Succinylbenzoate is invovled in the biosynthesis of menaquinone. o-Succinylbenzoate synthase (OSBS) from Escherichia coli, a member of the enolase superfamily, catalyzes an exergonic dehydration reaction in the menaquinone biosynthetic pathway in which 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (SHCHC) is converted to 4-(2'-carboxyphenyl)-4-oxobutyrate (o-succinylbenzoate or OSB). The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. (PMID 3902015 ) The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. coli strains synthesize an intermediate, "X", which is converted to OSB by extracts of menC+ cells. It was demonstrated that chorismate is the branch point compound leading to menaquinone, and that 2-succinylbenzoic acid and 1,4-dihydroxy-2-naphthoic acid can serve as menaquinoone precursors in E. coli. (PMID 1091286 ) The committed step in menaquinone biosynthesis is the formation of o-succinylbenzoate (OSB). (PMID 3516220 ) The suggestion is made that the spirodilactone is the product of an aberrant reaction involving a compound that is normally an intermediate in the conversion of 2-succinylbenzoate to 1,4-dihydroxy-2-naphthoate. (PMID 99177 ) The presence of shikimic acid in the growth medium restores the ability of an aroD mutant to synthesize cmo5U, while O-succinylbenzoate, which is an early intermediate in the synthesis of menaquinone, does not. (PMID 2104604 )

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 01211515262D          

 16 16  0  0  0  0            999 V2000
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 O   0  5  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
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
M  CHG  2  14  -1  16  -1
M  END
> <DATABASE_ID>
MMDBc0029982

> <DATABASE_NAME>
MIME

> <SMILES>
[O-]C(=O)CCC(=O)C1=CC=CC=C1C([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)/p-2

> <INCHI_KEY>
YIVWQNVQRXFZJB-UHFFFAOYSA-L

> <FORMULA>
C11H8O5

> <MOLECULAR_WEIGHT>
220.181

> <EXACT_MASS>
220.038270517

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
20.064720897416933

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-carboxylatopropanoyl)benzoate

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
1.0133389896666665

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.595760241001752

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4184310583310977

> <JCHEM_PKA_STRONGEST_BASIC>
-7.57018002288234

> <JCHEM_POLAR_SURFACE_AREA>
97.33000000000001

> <JCHEM_REFRACTIVITY>
76.28450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-succinylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JAN-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-15         0                                  
HETATM    1  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O-1
HETATM   15  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.335  10.780   0.000  0.00  0.00           O-1
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    3    8    9                                                  
CONECT    8    4    7   11                                                  
CONECT    9    5    7   12                                                  
CONECT   10    6   13   14                                                  
CONECT   11    8   15   16                                                  
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Synonyms

Value	Source
O-Succinatobenzoate	ChEBI
O-Succinylbenzoate	ChEBI
Succinylbenzoate	ChEBI
O-Succinatobenzoic acid	Generator
O-Succinylbenzoic acid	Generator
Succinylbenzoic acid	Generator
2-Succinylbenzoic acid	Generator
2-Succinylbenzoate	ChEBI
2-Succinatobenzoic acid	Generator

Molecular Formula

C₁₁H₈O₅

Average Mass

220.181

Monoisotopic Mass

220.038270517

IUPAC Name

2-(3-carboxylatopropanoyl)benzoate

Traditional Name

2-succinylbenzoate

CAS Registry Number

27415-09-4

SMILES

[O-]C(=O)CCC(=O)C1=CC=CC=C1C([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)/p-2

InChI Key

YIVWQNVQRXFZJB-UHFFFAOYSA-L

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for 2-Succinylbenzoate (MMDBc0029982)

MOL for #<Metabolite:0x00007f53943edc28>

3D MOL for #<Metabolite:0x00007f53943edc28>

3D SDF for #<Metabolite:0x00007f53943edc28>

3D-SDF for #<Metabolite:0x00007f53943edc28>

PDB for #<Metabolite:0x00007f53943edc28>

3D PDB for #<Metabolite:0x00007f53943edc28>

SMILES for #<Metabolite:0x00007f53943edc28>

INCHI for #<Metabolite:0x00007f53943edc28>

Structure for #<Metabolite:0x00007f53943edc28>

3D Structure for #<Metabolite:0x00007f53943edc28>