(3S,4R)-3,4,5-trihydroxypentan-2-one

• ChemBase ID: 154393
• Molecular Formular: C5H10O4
• Molecular Mass: 134.1305
• Monoisotopic Mass: 134.0579088
• SMILES: CC(=O)[C@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@@H](C(=O)C)O)O
• InChI: InChI=1S/C5H10O4/c1-3(7)5(9)4(8)2-6/h4-6,8-9H,2H2,1H3/t4-,5-/m1/s1
• InChIKey: IGUZJYCAXLYZEE-RFZPGFLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-3,4,5-trihydroxypentan-2-one
• IUPAC Traditional name: 1-deoxy-D-xylulose
• Synonyms: (3S,4R)-3,4,5-Trihydroxy-2-pentanone; 1-Deoxy-D-threo-2-pentulose; 1-Deoxy-D-xylulose

Database IDs

• CAS Number: 60299-43-6
• MDL Number: MFCD08460011
• PubChem SID: 162248532
• PubChem CID: 9548569

CALCULATED PROPERTIES

• Acid pKa: 12.247431
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.819449
• LogD (pH = 7.4): -1.819455
• Log P: -1.819449
• Molar Refractivity: 29.8971 cm^3
• Polarizability: 12.021338 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D +31.0±3.0°, c = 1 in H2O

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥80% (TLC)
• Empirical Formula (Hill Notation): C5H10O4

DETAILS

Sigma Aldrich - 14764

Biochem/physiol Actions
Metabolite of the non-mevalonate pathway, generally found in prokaryotes, as precursor to isoprenoids as well as non-isoprenoids like vitamins. As this pathway is not present in humans, it is of interest for the development of bacterium-specific drugs in the search for treatments of infectious diseases.
Linkage
In E. coli, 1-deoxy-D-xylulose is converted into 1-deoxy-D-xylulose 5-phosphate by phosphorylation of the C-5 hydroxy group by D-xylulokinase. 1