You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information |
---|
Version | 4.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2008-09-12 02:06:15 UTC |
---|
Update Date | 2019-01-11 19:27:31 UTC |
---|
HMDB ID | HMDB0010169 |
---|
Secondary Accession Numbers | - HMDB0012098
- HMDB10169
- HMDB12098
|
---|
Metabolite Identification |
---|
Common Name | SM(d18:1/16:0) |
---|
Description | Sphingomyelin (d18:1/16:0) or SM(d18:1/16:0) is a sphingomyelin. Sphingomyelin (SM or SPH) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. SM(18:1/16:0) consists of oleic acid attached to the C1 position and palmitic acid attached to the C2 position. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of Sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase. |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
C16 Sphingomyelin | HMDB | N-(Hexadecanoyl)-sphing-4-enine-1-phosphocholine | HMDB | Sphingomyelin | HMDB | Sphingomyelin (D18:1/16:0) | HMDB |
|
---|
Chemical Formula | C39H80N2O6P |
---|
Average Molecular Weight | 704.0361 |
---|
Monoisotopic Molecular Weight | 703.575399814 |
---|
IUPAC Name | {[(2S,3R,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid |
---|
Traditional Name | [(2S,3R,4E)-2-hexadecanamido-3-hydroxyoctadec-4-en-1-yl]oxy(2-(trimethylammonio)ethoxy)phosphinic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | CCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(O)(=O)OCC[N+](C)(C)C)[C@]([H])(O)\C=C\CCCCCCCCCCCCC |
---|
InChI Identifier | InChI=1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/p+1/b32-30+/t37-,38+/m0/s1 |
---|
InChI Key | RWKUXQNLWDTSLO-GWQJGLRPSA-O |
---|
Chemical Taxonomy |
---|
Description | This compound belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Sphingolipids |
---|
Sub Class | Phosphosphingolipids |
---|
Direct Parent | Phosphosphingolipids |
---|
Alternative Parents | |
---|
Substituents | - Sphingoid-1-phosphate or derivatives
- Phosphocholine
- Phosphoethanolamine
- Dialkyl phosphate
- Fatty amide
- N-acyl-amine
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Fatty acyl
- Alkyl phosphate
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Carboxylic acid derivative
- Organic salt
- Amine
- Alcohol
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic cation
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
|
Physiological effect | Organoleptic effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Industrial application: Biological role: |
---|
Physical Properties |
---|
State | Solid |
---|
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 | |
---|
|
---|
Spectra | Not Available |
---|
Biological Properties |
---|
Cellular Locations | |
---|
Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
|
---|
Tissue Locations | |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Blood | Detected and Quantified | 60.00-190.0 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 69.9 (61-79.4) uM | Newborn (0-30 days old) | Not Available | Normal | | details | Blood | Detected and Quantified | 121 (101-139) uM | Infant (0-1 year old) | Not Available | Normal | | details | Blood | Detected and Quantified | 81 +/- 0.9 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 114.4 +/- 19.7 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.336 +/- 0.109 uM | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected and Quantified | 0.282 +/- 0.145 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 8.92 +/- 0.59 umol/mmol creatinine | Adolescent (13-18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.01 (0.0016-0.07) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.0203 +/- 0.0374 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details |
|
---|
Abnormal Concentrations |
---|
| |
Blood | Detected and Quantified | 79.1 +/- 20.6 uM | Children (1-13 years old) | Both | Obesity | | details | Blood | Detected and Quantified | 86.1 +/- 23.2 uM | Children (1-13 years old) | Both | Obesity | | details | Feces | Detected but not Quantified | | Newborn (0-30 days old) | Not Specified | Premature neonates | | details | Urine | Detected and Quantified | 6.94 +/- 0.42 umol/mmol creatinine | Adolescent (13-18 years old) | Both | Obese | | details | Urine | Detected and Quantified | 0.0194 +/- 0.0383 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 0.0218 +/- 0.0369 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details |
|
---|
Associated Disorders and Diseases |
---|
Disease References | Eosinophilic esophagitis |
---|
- (). Mordechai, Hien, and David S. Wishart. .
| Obesity |
---|
- Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]
- Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
|
|
---|
Associated OMIM IDs | |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FoodDB ID | FDB027352 |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | 4446703 |
---|
KEGG Compound ID | C00550 |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 5283590 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 17636 |
---|
References |
---|
Synthesis Reference | Not Available |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
General References | Not Available |
---|