Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-05-11 19:00:56 UTC |
---|
Updated at | 2022-05-11 19:00:57 UTC |
---|
NP-MRD ID | NP0092232 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | SM(d18:0/16:1(9Z)(OH)) |
---|
Description | SM(d18:0/16:1(9Z)(OH)), also known as C16:1-OH sphingomyelin or SM(D18:1/16:1(9Z)(OH)), 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. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down SM(d18:0/16:1(9Z)(OH)) into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be SM(d18:0/16:1(9Z)(OH)) present there. SM(d18:0/16:1(9Z)(OH)) is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, SM(d18:0/16:1(9Z)(OH)) has been detected, but not quantified in, several different foods, such as cow milks, cow milks, cow milks, and cow milks. This could make SM(D18:0/16:1(9Z)(OH)) a potential biomarker for the consumption of these foods. SM(d18:0/16:1(9Z)(OH)) (d18:0/16:1(9Z)(OH)) or SM(d18:0/16:1(9Z)(OH))is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. In humans, SM(d18:0/16:1(9Z)(OH)) is the only membrane phospholipid not derived from glycerol. However, there is some evidence that there may also be a SM(d18:0/16:1(9Z)(OH)) pool in the inner leaflet of the membrane. It was first documented in 1994 (PMID: 8106344). SMs play a role in signal transduction (PMID: 9034165) (PMID: 24023812) (PMID: 7834746) (PMID: 22546835). |
---|
Structure | CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CC(O)CCCCC\C=C/CCCCCC InChI=1S/C39H77N2O7P/c1-6-8-10-12-14-16-18-19-21-23-25-27-29-31-38(43)37(35-48-49(45,46)47-33-32-41(3,4)5)40-39(44)34-36(42)30-28-26-24-22-20-17-15-13-11-9-7-2/h17,20,29,31,36-38,42-43H,6-16,18-19,21-28,30,32-35H2,1-5H3,(H-,40,44,45,46)/b20-17-,31-29+/t36?,37-,38+/m0/s1 |
---|
Synonyms | Value | Source |
---|
C16:1-OH Sphingomyelin | ChEBI | Hydroxysphingomyeline C16:1 | ChEBI | N-[(9Z)-3-Hydroxyhexadec-9-enoyl]sphing-4-enine-1-phosphocholine | ChEBI | SM(D18:1/16:1(9Z)(OH)) | ChEBI | N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholine | HMDB | Sphingomyelin | MetBuilder | N-(3-Hydroxy-9Z-hexadecenoyl)-1-phosphocholine-sphinganine | MetBuilder | Sphingomyelin(D18:0/16:1(9Z)(OH)) | MetBuilder | N-(3-Hydroxy-9Z-hexadecenoyl)-1-phosphocholine-dihydrosphingosine | MetBuilder | N-(3-Hydroxy-9Z-hexadecenoyl)-1-phosphocholine-D-erythro-sphinganine | MetBuilder |
|
---|
Chemical Formula | C39H77N2O7P |
---|
Average Mass | 717.0116 Da |
---|
Monoisotopic Mass | 716.54684 Da |
---|
IUPAC Name | (2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium |
---|
Traditional Name | (2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium |
---|
CAS Registry Number | Not Available |
---|
SMILES | CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CC(O)CCCCC\C=C/CCCCCC |
---|
InChI Identifier | InChI=1S/C39H77N2O7P/c1-6-8-10-12-14-16-18-19-21-23-25-27-29-31-38(43)37(35-48-49(45,46)47-33-32-41(3,4)5)40-39(44)34-36(42)30-28-26-24-22-20-17-15-13-11-9-7-2/h17,20,29,31,36-38,42-43H,6-16,18-19,21-28,30,32-35H2,1-5H3,(H-,40,44,45,46)/b20-17-,31-29+/t36?,37-,38+/m0/s1 |
---|
InChI Key | LPHMSPONPQCKTL-FKUNDBCPSA-N |
---|
Experimental Spectra |
---|
|
| Not Available | Predicted Spectra |
---|
|
| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
Chemical Taxonomy |
---|
Description | 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 zwitterion
- Alcohol
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Amine
- Organic salt
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | Not Available |
---|
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 | - Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
- Bouatra S, Aziat F, Mandal R, Guo AC, Wilson MR, Knox C, Bjorndahl TC, Krishnamurthy R, Saleem F, Liu P, Dame ZT, Poelzer J, Huynh J, Yallou FS, Psychogios N, Dong E, Bogumil R, Roehring C, Wishart DS: The human urine metabolome. PLoS One. 2013 Sep 4;8(9):e73076. doi: 10.1371/journal.pone.0073076. eCollection 2013. [PubMed:24023812 ]
- Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. doi: 10.1016/0092-8674(95)90409-3. [PubMed:7834746 ]
- Mandal R, Guo AC, Chaudhary KK, Liu P, Yallou FS, Dong E, Aziat F, Wishart DS: Multi-platform characterization of the human cerebrospinal fluid metabolome: a comprehensive and quantitative update. Genome Med. 2012 Apr 30;4(4):38. doi: 10.1186/gm337. [PubMed:22546835 ]
- Hannun YA: The sphingomyelin cycle and the second messenger function of ceramide. J Biol Chem. 1994 Feb 4;269(5):3125-8. [PubMed:8106344 ]
|
---|