MiMeDB: Showing metabocard for O-Succinyl-L-homoserine (MMDBc0029648)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:36:02 UTC

Update Date

2022-08-31 14:16:26 UTC

Metabolite ID

MMDBc0029648

Metabolite Identification

Common Name

O-Succinyl-L-homoserine

Description

O-succinyl-L-homoserine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).O-succinyl-L-homoserine is involved in bacterial transfulfuration pathway. Cystathionine gamma-synthase (CGS) is a pyridoxal phosphate-dependent enzyme that catalyzes a gamma-replacement reaction, in which the succinyl group of an O-succinyl-L-homoserine (L-OSHS) is displaced by the thiol of L-cysteine to form L-cystathionine, in the first step of the bacterial transsulfuration pathway. Cystathionine gamma-synthase (CGS) is a pyridoxal phosphate-dependent enzyme that catalyzes a gamma-replacement reaction, in which the succinyl group of an O-succinyl-L-homoserine (L-OSHS) is displaced by the thiol of L-cysteine to form L-cystathionine, in the first step of the bacterial transsulfuration pathway. (PMID 14503880 )

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1652303062005542D          

 15 14  0  0  1  0            999 V2000
   27.6994  -16.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4149  -16.3531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6994  -17.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1341  -16.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8497  -16.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5650  -16.7640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   31.2843  -16.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5688  -17.5937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9998  -16.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2843  -15.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9879  -16.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2886  -16.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5941  -16.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8987  -16.7651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5932  -15.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  1  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029648

> <DATABASE_NAME>
MIME

> <SMILES>
N[C@@H](CCOC(=O)CCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H13NO6/c9-5(8(13)14)3-4-15-7(12)2-1-6(10)11/h5H,1-4,9H2,(H,10,11)(H,13,14)/t5-/m0/s1

> <INCHI_KEY>
GNISQJGXJIDKDJ-YFKPBYRVSA-N

> <FORMULA>
C8H13NO6

> <MOLECULAR_WEIGHT>
219.1919

> <EXACT_MASS>
219.074287153

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.513811131589183

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-[(3-carboxypropanoyl)oxy]butanoic acid

> <ALOGPS_LOGP>
-3.31

> <JCHEM_LOGP>
-3.6100642791309556

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.112459497104107

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.688067433289202

> <JCHEM_PKA_STRONGEST_BASIC>
9.458196258009957

> <JCHEM_POLAR_SURFACE_AREA>
126.92000000000002

> <JCHEM_REFRACTIVITY>
46.95120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-succinyl-L-homoserine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0      51.706 -31.300   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      53.041 -30.526   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      51.706 -32.842   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      54.384 -31.293   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      55.719 -30.526   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      57.055 -31.293   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      58.397 -30.518   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      57.062 -32.842   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      59.733 -31.293   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      58.397 -29.210   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      50.377 -30.535   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      49.072 -31.291   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      47.776 -30.544   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      46.478 -31.295   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      47.774 -29.010   0.000  0.00  0.00           O+0
CONECT    1    2    3   11                                                  
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    9   10                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    1   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

Synonyms

Value	Source
O-Succinylhomoserine	ChEBI
O4-Succinyl-L-homoserine	ChEBI
O-Succinylhomoserine, (DL)-isomer	MeSH

Molecular Formula

C₈H₁₃NO₆

Average Mass

219.1919

Monoisotopic Mass

219.074287153

IUPAC Name

(2S)-2-amino-4-[(3-carboxypropanoyl)oxy]butanoic acid

Traditional Name

O-succinyl-L-homoserine

CAS Registry Number

1492-23-5

SMILES

N[C@@H](CCOC(=O)CCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C8H13NO6/c9-5(8(13)14)3-4-15-7(12)2-1-6(10)11/h5H,1-4,9H2,(H,10,11)(H,13,14)/t5-/m0/s1

InChI Key

GNISQJGXJIDKDJ-YFKPBYRVSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-9600000000-0ee701fa496e19e3d173	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-1950000000-5b18c68cf76a73eb1d8f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pi0-7900000000-3331dd355814be8ede11	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9400000000-146c8b009d4e75570320	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014j-7690000000-0163fcb4afd466414db2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ba-9720000000-dd9470ad7562bdf591b1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05tb-9200000000-ae21c8bfb909ac97af60	2015-09-15	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

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 O-Succinyl-L-homoserine (MMDBc0029648)

MOL for #<Metabolite:0x00007f53b55e48a8>

3D MOL for #<Metabolite:0x00007f53b55e48a8>

3D SDF for #<Metabolite:0x00007f53b55e48a8>

3D-SDF for #<Metabolite:0x00007f53b55e48a8>

PDB for #<Metabolite:0x00007f53b55e48a8>

3D PDB for #<Metabolite:0x00007f53b55e48a8>

SMILES for #<Metabolite:0x00007f53b55e48a8>

INCHI for #<Metabolite:0x00007f53b55e48a8>

Structure for #<Metabolite:0x00007f53b55e48a8>

3D Structure for #<Metabolite:0x00007f53b55e48a8>