MiMeDB: Showing metabocard for S(8)-succinyldihydrolipoamide (MMDBc0033112)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:35:17 UTC

Update Date

2024-04-30 20:00:28 UTC

Metabolite ID

MMDBc0033112

Metabolite Identification

Common Name

S(8)-succinyldihydrolipoamide

Description

(S)-Succinyldihydrolipoamide is an organosulfur compound derived from Lipoic acid. (S)-Succinyldihydrolipoamide is an intermediate in the transfer of a succinyl group from oxogluterate via the oxoglutarate dehydrogenase complex (Œ±-ketoglutarate dehydrogenase complex). The oxoglutarate dehydrogenase complex is a complement of the citric acid (Krebs) cycle.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222352D          
 
 19 18  0  0  0  0            999 V2000
    3.5724   -0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.2200    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.1925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.1925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0176    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    1.0449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.0176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.0450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3 16  1  0  0  0  0
  3  4  1  0  0  0  0
  5  2  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  6 19  2  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 18  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 17  2  0  0  0  0
 13 14  1  0  0  0  0
  6 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033112

> <DATABASE_NAME>
MIME

> <SMILES>
NC(=O)CCCCC(S)CCSC(=O)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO4S2/c13-10(14)4-2-1-3-9(18)7-8-19-12(17)6-5-11(15)16/h9,18H,1-8H2,(H2,13,14)(H,15,16)

> <INCHI_KEY>
KWKBJWYJJBQOAE-UHFFFAOYSA-N

> <FORMULA>
C12H21NO4S2

> <MOLECULAR_WEIGHT>
307.429

> <EXACT_MASS>
307.091199545

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.254466646005966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(7-carbamoyl-3-sulfanylheptyl)sulfanyl]-4-oxobutanoic acid

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
1.061330826

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.059201445823641

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.215974213209748

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5791168859159223

> <JCHEM_POLAR_SURFACE_AREA>
97.46000000000001

> <JCHEM_REFRACTIVITY>
78.11989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
S(8)-succinyldihydrolipoamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       6.668  -0.359   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   0.411   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.359   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.411   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.411   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.411   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.359   0.000  0.00  0.00           C+0
HETATM    9  S   UNK     0      -2.667   0.411   0.000  0.00  0.00           S+0
HETATM   10  C   UNK     0      -4.001  -0.359   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   0.411   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668  -0.359   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002   0.411   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -9.336  -0.359   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       9.336  -0.359   0.000  0.00  0.00           N+0
HETATM   16  S   UNK     0       1.334  -1.900   0.000  0.00  0.00           S+0
HETATM   17  O   UNK     0      -8.002   1.950   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.001  -1.900   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.002   1.951   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    5                                                       
CONECT    3   16    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    2    4                                                       
CONECT    6    1   19   15                                                  
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   18   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   17   14                                                  
CONECT   14   13                                                            
CONECT   15    6                                                            
CONECT   16    3                                                            
CONECT   17   13                                                            
CONECT   18   10                                                            
CONECT   19    6                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

Synonyms

Value	Source
S-Succinyldihydrolipoamide	ChEBI

Molecular Formula

C₁₂H₂₁NO₄S₂

Average Mass

307.429

Monoisotopic Mass

307.091199545

IUPAC Name

4-[(7-carbamoyl-3-sulfanylheptyl)sulfanyl]-4-oxobutanoic acid

Traditional Name

S(8)-succinyldihydrolipoamide

CAS Registry Number

Not Available

SMILES

NC(=O)CCCCC(S)CCSC(=O)CCC(O)=O

InChI Identifier

InChI=1S/C12H21NO4S2/c13-10(14)4-2-1-3-9(18)7-8-19-12(17)6-5-11(15)16/h9,18H,1-8H2,(H2,13,14)(H,15,16)

InChI Key

KWKBJWYJJBQOAE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Thia fatty acids

Alternative Parents

Substituents

Thia fatty acid
Fatty acyl thioester
Fatty amide
Carboxamide group
Primary carboxylic acid amide
Thiocarboxylic acid ester
Carbothioic s-ester
Sulfenyl compound
Thiocarboxylic acid or derivatives
Alkylthiol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

S-substituted dihydrolipoamide (CHEBI:17432 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.082 g/L	ALOGPS
logP	1.94	ALOGPS
logP	1.06	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-0.58	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	97.46 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	78.12 m³·mol⁻¹	ChemAxon
Polarizability	33.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-8790000000-e55ecedd6751558a3cc0	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0abc-0591000000-68ceeee1aef07ecc7bca	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-1790000000-754724dd70bfb1ccb6ca	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0mbi-8900000000-aaca13771ecaf5ee69cd	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-4493000000-9bc9b7996f912788eb1c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0592-9450000000-05e7b3f01cf7898f1ac7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-0e7f89fa1f0d117b1aab	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0060556

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01169

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11953795

PDB ID

Not Available

ChEBI ID

17432

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for S(8)-succinyldihydrolipoamide (MMDBc0033112)

MOL for #<Metabolite:0x00005634c27895b8>

3D MOL for #<Metabolite:0x00005634c27895b8>

3D SDF for #<Metabolite:0x00005634c27895b8>

3D-SDF for #<Metabolite:0x00005634c27895b8>

PDB for #<Metabolite:0x00005634c27895b8>

3D PDB for #<Metabolite:0x00005634c27895b8>

SMILES for #<Metabolite:0x00005634c27895b8>

INCHI for #<Metabolite:0x00005634c27895b8>

Structure for #<Metabolite:0x00005634c27895b8>

3D Structure for #<Metabolite:0x00005634c27895b8>