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Showing metabocard for Succinylcarnitine (HMDB0061717)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-04-16 20:46:53 UTC
Update Date2020-02-26 19:17:41 UTC
HMDB IDHMDB0061717
Secondary Accession Numbers
  • HMDB61717
Metabolite Identification
Common NameSuccinylcarnitine
DescriptionSuccinylcarnitine (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
Data?1568988572
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
O-SuccinylcarnitineHMDB
Chemical FormulaC11H19NO6
Average Molecular Weight261.274
Monoisotopic Molecular Weight261.121237336
IUPAC Name(3R)-3-[(3-carboxypropanoyl)oxy]-4-(trimethylazaniumyl)butanoate
Traditional Name(3R)-3-[(3-carboxypropanoyl)oxy]-4-(trimethylammonio)butanoate
CAS Registry Number256928-74-2
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 KeyHAEVNYBCYZZDFL-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl 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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP-2.1ALOGPS
logP-4.6ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.73 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity83.53 m³·mol⁻¹ChemAxon
Polarizability25.67 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID62896353
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131802075
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.