CHEBI:144948 - VPC 23019

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ChEBI Name VPC 23019
ChEBI ID CHEBI:144948
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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Sabrina Toro
Supplier Information
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Formula C17H29N2O5P
Net Charge 0
Average Mass 372.402
Monoisotopic Mass 372.18141
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
SMILES P(O)(OC[C@H](C(=O)NC=1C=C(CCCCCCCC)C=CC1)N)(=O)O
Roles Classification
Biological Role(s): 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).
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ChEBI Ontology
Outgoing 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
(2R)-2-amino-3-(3-octylanilino)-3-oxopropyl dihydrogen phosphate
N-(3-octylphenyl)-O-phosphono-D-serinamide
Synonyms Sources
(2R)-2-amino-N-(3-octylphenyl)-3-(phosphonooxy)-propanamide SUBMITTER
(R)-phosphoric acid mono-[2-amino-2-(3-octyl-phenylcarbamoyl)-ethyl] ester ChEBI
VPC-23019 ChEBI
VPC23019 ChEBI
Registry Number Type Source
449173-19-7 CAS Registry Number SUBMITTER
Citations Waiting for Citations Types Sources
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Last Modified
27 September 2019