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CHEBI:144948 - VPC 23019
| ChEBI ID | CHEBI:144948 |
| ChEBI Name | VPC 23019 |
| Stars | |
| Definition | A secondary carboxamide resulting from the formal condensation of the carboxy group of O-phospho-D-serine with the amino group of m-octylaniline. An analogue of sphingosine-1-phosphate (S1P), it is a potent antagonist for both S1P1 and S1P3 receptors. It can inhibit S1P-induced migration of thyroid cancer cells, ovarian cancer cells, and neural stem cells. |
| Last Modified | 27 September 2019 |
| Submitter | sabrina, zfin |
| Downloads |
| Formula | C17H29N2O5P |
| Net Charge | 0 |
| Average Mass | 372.402 |
| Monoisotopic Mass | 372.18141 |
| SMILES | CCCCCCCCc1cccc(NC(=O)[C@H](N)COP(=O)(O)O)c1 |
| InChI | InChI=1S/C17H29N2O5P/c1-2-3-4-5-6-7-9-14-10-8-11-15(12-14)19-17(20)16(18)13-24-25(21,22)23/h8,10-12,16H,2-7,9,13,18H2,1H3,(H,19,20)(H2,21,22,23)/t16-/m1/s1 |
| InChIKey | MRUSUGVVWGNKFE-MRXNPFEDSA-N |
| Roles Classification |
|---|
| Biological Roles: | sphingosine-1-phosphate receptor 3 antagonist Any sphingosine-1-phosphate receptor (S1PR) antagonist that acts as an antagonist towards the subtype 3 receptors (S1PR3). sphingosine-1-phosphate receptor 1 antagonist Any sphingosine-1-phosphate receptor (S1PR) antagonist that acts as an antagonist for the subtype 1 receptors (S1PR1). |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| VPC 23019 (CHEBI:144948) has functional parent O-phospho-D-serine (CHEBI:37713) |
| VPC 23019 (CHEBI:144948) has role sphingosine-1-phosphate receptor 1 antagonist (CHEBI:144998) |
| VPC 23019 (CHEBI:144948) has role sphingosine-1-phosphate receptor 3 antagonist (CHEBI:144997) |
| VPC 23019 (CHEBI:144948) is a D-serine derivative (CHEBI:84133) |
| VPC 23019 (CHEBI:144948) is a aromatic amide (CHEBI:62733) |
| VPC 23019 (CHEBI:144948) is a organic phosphate (CHEBI:25703) |
| VPC 23019 (CHEBI:144948) is a phosphoric ester (CHEBI:37734) |
| VPC 23019 (CHEBI:144948) is a secondary carboxamide (CHEBI:140325) |
| IUPAC Names |
|---|
| N-(3-octylphenyl)-O-phosphono-D-serinamide |
| (2R)-2-amino-3-(3-octylanilino)-3-oxopropyl dihydrogen phosphate |
| Synonyms | Source |
|---|---|
| (2R)-2-amino-N-(3-octylphenyl)-3-(phosphonooxy)-propanamide | SUBMITTER |
| (R)-phosphoric acid mono-[2-amino-2-(3-octyl-phenylcarbamoyl)-ethyl] ester | ChEBI |
| VPC23019 | ChEBI |
| VPC-23019 | ChEBI |
| Registry Numbers | Sources |
|---|---|
| CAS:449173-19-7 | SUBMITTER |
| Citations |
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