| Record Information |
|---|
| Version | 4.0 |
|---|
| Status | Detected but not Quantified |
|---|
| Creation Date | 2014-04-16 20:46:53 UTC |
|---|
| Update Date | 2020-11-09 23:22:00 UTC |
|---|
| HMDB ID | HMDB0061717 |
|---|
| Secondary Accession Numbers | |
|---|
| Metabolite Identification |
|---|
| Common Name | Succinylcarnitine |
|---|
| Description | Succinylcarnitine (C4DC) arises from the TCA cycle intermediate succinyl-CoA in plasma and liver. It is an O-acylcarnitine having succinyl as the acyl substituent. It functions as a secondary metabolite, which is a metabolite that is not directly involved in the normal growth, development, or reproduction of an organism. Succinylcarnitine has been identified in the human placenta (PMID: 32033212 ). |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| O-Succinylcarnitine | HMDB |
|
|---|
| Chemical Formula | C11H19NO6 |
|---|
| Average Molecular Weight | 261.274 |
|---|
| Monoisotopic Molecular Weight | 261.121237336 |
|---|
| IUPAC Name | (3R)-3-[(3-carboxypropanoyl)oxy]-4-(trimethylazaniumyl)butanoate |
|---|
| Traditional Name | (3R)-3-[(3-carboxypropanoyl)oxy]-4-(trimethylammonio)butanoate |
|---|
| CAS Registry Number | 256928-74-2 |
|---|
| SMILES | C[N+](C)(C)C[C@@H](CC([O-])=O)OC(=O)CCC(O)=O |
|---|
| InChI Identifier | InChI=1S/C11H19NO6/c1-12(2,3)7-8(6-10(15)16)18-11(17)5-4-9(13)14/h8H,4-7H2,1-3H3,(H-,13,14,15,16)/t8-/m1/s1 |
|---|
| InChI Key | HAEVNYBCYZZDFL-MRVPVSSYSA-N |
|---|
| Chemical Taxonomy |
|---|
| Description | belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Fatty Acyls |
|---|
| Sub Class | Fatty acid esters |
|---|
| Direct Parent | Acyl carnitines |
|---|
| Alternative Parents | |
|---|
| Substituents | - Acyl-carnitine
- Tricarboxylic acid or derivatives
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Carboxylic acid ester
- Carboxylic acid salt
- Carboxylic acid derivative
- Carboxylic acid
- Organic nitrogen compound
- Organic salt
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Amine
- Aliphatic acyclic compound
|
|---|
| Molecular Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Ontology |
|---|
|
| Disposition | Route of exposure: Source: Biological location: |
|---|
| Process | Naturally occurring process: |
|---|
| Role | Biological role: |
|---|
| Physical Properties |
|---|
| State | Not Available |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [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. 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. 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 ]
- Van Hove JL, Saenz MS, Thomas JA, Gallagher RC, Lovell MA, Fenton LZ, Shanske S, Myers SM, Wanders RJ, Ruiter J, Turkenburg M, Waterham HR: Succinyl-CoA ligase deficiency: a mitochondrial hepatoencephalomyopathy. Pediatr Res. 2010 Aug;68(2):159-64. doi: 10.1203/00006450-201011001-00310. [PubMed:20453710 ]
- Jaberi E, Chitsazian F, Ali Shahidi G, Rohani M, Sina F, Safari I, Malakouti Nejad M, Houshmand M, Klotzle B, Elahi E: The novel mutation p.Asp251Asn in the beta-subunit of succinate-CoA ligase causes encephalomyopathy and elevated succinylcarnitine. J Hum Genet. 2013 Aug;58(8):526-30. doi: 10.1038/jhg.2013.45. Epub 2013 Jun 13. [PubMed:23759946 ]
- Huffman KM, Koves TR, Hubal MJ, Abouassi H, Beri N, Bateman LA, Stevens RD, Ilkayeva OR, Hoffman EP, Muoio DM, Kraus WE: Metabolite signatures of exercise training in human skeletal muscle relate to mitochondrial remodelling and cardiometabolic fitness. Diabetologia. 2014 Nov;57(11):2282-95. doi: 10.1007/s00125-014-3343-4. Epub 2014 Aug 5. [PubMed:25091629 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
|
|---|
