[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid hydrate

• ChemBase ID: 155984
• Molecular Formular: C8H12NO7P
• Molecular Mass: 265.157141
• Monoisotopic Mass: 265.03513836
• SMILES: Cc1c(c(c(cn1)COP(=O)(O)O)C=O)O.O
• Canonical SMILES: O=Cc1c(COP(=O)(O)O)cnc(c1O)C.O
• InChI: InChI=1S/C8H10NO6P.H2O/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14;/h2-3,11H,4H2,1H3,(H2,12,13,14);1H2
• InChIKey: CEEQUQSGVRRXQI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid hydrate
• IUPAC Traditional name: hydrate pyridoxal phosphate
• Synonyms: 3-Hydroxy-2-methyl-5-([phosphonooxy]methyl)-4-pyridinecarboxaldehyde; Codecarboxylase; P5P; PLP; Pyridoxal 5-phosphate; Pyridoxal 5′-phosphate monohydrate; Pyridoxal-5-phosphate monohydrate; 吡哆醛-5-磷酸单水合物

Database IDs

• CAS Number: 41468-25-1
• MDL Number: MFCD00149414
• Beilstein Number: 234749
• Merck Index: 147979
• PubChem SID: 162250122; 24888057
• PubChem CID: 38882

CALCULATED PROPERTIES

• Acid pKa: 1.6802986
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.3409967
• LogD (pH = 7.4): -3.1810691
• Log P: -2.0856087
• Molar Refractivity: 54.7463 cm^3
• Polarizability: 20.725895 Å^3
• Polar Surface Area: 116.95 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 140-143 °C(lit.); 140-143°C

Safety Information

• RTECS: UV1208000
• German water hazard class: 2
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (NT); 98%
• Cation Traces: Ca: ≤20 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤50 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤2000 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤500 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Empirical Formula (Hill Notation): C8H10NO6P · H2O

DETAILS

Sigma Aldrich - 82870

Other Notes
Coenzymes and Cofactors, vol. 1: Vitamin B6, Pyridoxal Phosphate1,2
Application
Pyridoxal 5-phosphate (PLP) (active form of Vitamin B6) is an enzyme prosthetic group that acts as a coenzyme in transamination, decarboxylation and deamination reactions such as the conversion of dopa into dopamine; of glutamate into GABA; of histidine to histamine. PLP works mechanistically through formation of a Schiff-base.