sodium (3S,4R)-5-(hydrogen phosphonatooxy)-1,3,4-trihydroxypentan-2-one

• ChemBase ID: 153094
• Molecular Formular: C5H10NaO8P
• Molecular Mass: 252.091631
• Monoisotopic Mass: 252.00109819
• SMILES: C([C@H]([C@@H](C(=O)CO)O)O)OP(=O)(O)[O-].[Na+]
• Canonical SMILES: OCC(=O)[C@H]([C@@H](COP(=O)(O)[O-])O)O.[Na+]
• InChI: InChI=1S/C5H11O8P.Na/c6-1-3(7)5(9)4(8)2-13-14(10,11)12;/h4-6,8-9H,1-2H2,(H2,10,11,12);/q;+1/p-1/t4-,5-;/m1./s1
• InChIKey: OVHWWORCLJVDMI-TYSVMGFPSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3S,4R)-5-(hydrogen phosphonatooxy)-1,3,4-trihydroxypentan-2-one
• IUPAC Traditional name: sodium (3S,4R)-5-(hydrogen phosphonatooxy)-1,3,4-trihydroxypentan-2-one
• Synonyms: Xu-5-P; D-Xylulose 5-phosphate sodium salt; Xu-5-P monosodium salt; D-Xylulose 5-phosphate monosodium salt

Database IDs

• CAS Number: 105931-44-0
• MDL Number: MFCD00070073
• PubChem SID: 24890198; 162247234; 24849717
• PubChem CID: 23679045

CALCULATED PROPERTIES

• Acid pKa: 1.4785529
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -5.1677957
• LogD (pH = 7.4): -6.070068
• Log P: -2.760263
• Molar Refractivity: 41.3505 cm^3
• Polarizability: 17.253592 Å^3
• Polar Surface Area: 147.35 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~30% (enzymatic); ~75% (enzymatic); ≥90% (TLC)
• Empirical Formula (Hill Notation): C5H10NaO8P; C5H11O8P · xNa+

DETAILS

Sigma Aldrich - 15807

Biochem/physiol Actions
Xylulose-5-phoshate (Xu-5-P) is a metabolite of glucose via the pentose phosphate pathway. In the presence of excess glucose, liver Xu-5-P may act as a signaling molecule that regulates the nuclear transport of carbohydrate response element binding protein (ChREBP), a transcription factor that induces the expression of enzymes involved in glucose metabolism and lipogenesis.
Application
Xylulose-5-phoshate (Xu-5-P) is an activator of a class of protein phosphatase(s) such as protein phosphatase 2A in rat liver which catalyzed the dephosphorylation of Fru-6-P,2-kinase:Fru-2,6-Pase and protein phosphatases involved in the regulation of carbohydrate-responsive element binding protein (ChREBP) signaling.

Sigma Aldrich - X0754

Biochem/physiol Actions
Xylulose-5-phoshate (Xu-5-P) is a metabolite of glucose via the pentose phosphate pathway. In the presence of excess glucose, liver Xu-5-P may act as a signaling molecule that regulates the nuclear transport of carbohydrate response element binding protein (ChREBP), a transcription factor that induces the expression of enzymes involved in glucose metabolism and lipogenesis.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. X0754.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 95746

Biochem/physiol Actions
Xylulose-5-phoshate (Xu-5-P) is a metabolite of glucose via the pentose phosphate pathway. In the presence of excess glucose, liver Xu-5-P may act as a signaling molecule that regulates the nuclear transport of carbohydrate response element binding protein (ChREBP), a transcription factor that induces the expression of enzymes involved in glucose metabolism and lipogenesis.