Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-09-05 18:46:23 UTC |
---|
Updated at | 2022-09-05 18:46:23 UTC |
---|
NP-MRD ID | NP0218193 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | (2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid |
---|
Description | PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0), Also known as phosphatidylserine(22:6/18:0) Or PS(22:6/18:0), Belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. Thus, PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) Is considered to be a glycerophosphoserine lipid molecule. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) Is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) Participates in a number of enzymatic reactions. In particular, choline and PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) Can be biosynthesized from PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) And L-serine; which is mediated by the enzyme phosphatidylserine synthase. In addition, PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) Can be converted into PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0); Which is mediated by the enzyme phosphatidylserine decarboxylase. In humans, PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) Is involved in phosphatidylethanolamine biosynthesis. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.E. (2s)-2-amino-3-{[(2r)-3-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid is found in Aphis gossypii. It was first documented in 1995 (PMID: 7834746). The phosphate moiety, the amino group and the carboxyl function (PMID: 11413487) (PMID: 16902246) (PMID: 17374880) (PMID: 20044567). |
---|
Structure | [H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCCCC)C(O)=O InChI=1S/C46H78NO10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-25-27-29-31-33-35-37-44(48)54-39-42(40-55-58(52,53)56-41-43(47)46(50)51)57-45(49)38-36-34-32-30-28-26-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,25,27,31,33,42-43H,3-4,6,8-10,12,14-16,18,20,23-24,26,28-30,32,34-41,47H2,1-2H3,(H,50,51)(H,52,53)/b7-5-,13-11-,19-17-,22-21-,27-25-,33-31-/t42-,43+/m1/s1 |
---|
Synonyms | Value | Source |
---|
1-Docosahexaenoyl-2-stearoyl-sn-glycero-3-phosphoserine | HMDB | Phosphatidylserine(22:6/18:0) | HMDB | Phosphatidylserine(22:6n3/18:0) | HMDB | Phosphatidylserine(22:6W3/18:0) | HMDB | Phosphatidylserine(40:6) | HMDB | PS(22:6/18:0) | HMDB | PS(22:6N3/18:0) | HMDB | PS(22:6W3/18:0) | HMDB | PS(40:6) | HMDB | pSer(22:6/18:0) | HMDB | pSer(22:6n3/18:0) | HMDB | pSer(22:6W3/18:0) | HMDB | pSer(40:6) | HMDB | 1-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-2-octadecanoyl-sn-glycero-3-phosphoserine | HMDB | PS(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) | Lipid Annotator |
|
---|
Chemical Formula | C46H78NO10P |
---|
Average Mass | 836.0860 Da |
---|
Monoisotopic Mass | 835.53633 Da |
---|
IUPAC Name | (2S)-2-amino-3-({[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid |
---|
Traditional Name | (2S)-2-amino-3-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | [H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCCCC)C(O)=O |
---|
InChI Identifier | InChI=1S/C46H78NO10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-25-27-29-31-33-35-37-44(48)54-39-42(40-55-58(52,53)56-41-43(47)46(50)51)57-45(49)38-36-34-32-30-28-26-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,25,27,31,33,42-43H,3-4,6,8-10,12,14-16,18,20,23-24,26,28-30,32,34-41,47H2,1-2H3,(H,50,51)(H,52,53)/b7-5-,13-11-,19-17-,22-21-,27-25-,33-31-/t42-,43+/m1/s1 |
---|
InChI Key | YZPDRIODLGOXPQ-VQXQEPRVSA-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, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, 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 phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Glycerophospholipids |
---|
Sub Class | Glycerophosphoserines |
---|
Direct Parent | Phosphatidylserines |
---|
Alternative Parents | |
---|
Substituents | - Diacyl-glycerol-3-phosphoserine
- Alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- Tricarboxylic acid or derivatives
- Phosphoethanolamine
- Fatty acid ester
- Dialkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Amino acid
- Amino acid or derivatives
- Carboxylic acid ester
- Carboxylic acid derivative
- Carboxylic acid
- Primary aliphatic amine
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Amine
- Carbonyl group
- Organic oxide
- Primary amine
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
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 | |
---|