2-amino-3-(phosphonooxy)propanoic acid

• ChemBase ID: 155953
• Molecular Formular: C3H8NO6P
• Molecular Mass: 185.072481
• Monoisotopic Mass: 185.00892361
• SMILES: C(C(C(=O)O)N)OP(=O)(O)O
• Canonical SMILES: OC(=O)C(COP(=O)(O)O)N
• InChI: InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
• InChIKey: BZQFBWGGLXLEPQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-(phosphonooxy)propanoic acid
• IUPAC Traditional name: P-serine
• Synonyms: DL-2-Amino-3-hydroxypropanoic acid 3-phosphate; DL-SOP; DL-Serine monophosphoric acid; O-Phospho-DL-serine

Database IDs

• CAS Number: 17885-08-4
• EC Number: 241-834-7
• MDL Number: MFCD00021723
• Beilstein Number: 1726828
• PubChem SID: 162250091; 24887498
• PubChem CID: 106

CALCULATED PROPERTIES

• Acid pKa: 1.1985006
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -6.087564
• LogD (pH = 7.4): -7.322204
• Log P: -3.180275
• Molar Refractivity: 32.9139 cm^3
• Polarizability: 13.703259 Å^3
• Polar Surface Area: 130.08 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Purity: ≥98.0% (NT)
• Impurities: ≤0.5% free serine (TLC); ≤1% water
• Empirical Formula (Hill Notation): C3H8NO6P

DETAILS

Sigma Aldrich - 79710

Biochem/physiol Actions
O-Phospho-DL-serine (pSer) is used in the study of non-enzymatic aminophospholipid glycation.
O-Phosphoserine is used in alternative pathways for biosynthesis of cysteine and of selenocysteine (Sec) by tRNA-dependent conversion of O-phosphoserine (Sep) by O-phosphoseryl-tRNA:selenocysteinyl-tRNA synthase (SepSecS).