(2S,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid triamine

• ChemBase ID: 156328
• Molecular Formular: C15H31N5O18P2
• Molecular Mass: 631.376862
• Monoisotopic Mass: 631.11393244
• SMILES: c1cn(c(=O)[nH]c1=O)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(O)OP(=O)(O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)O)O.N.N.N
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(O[C@H]2O[C@H](C(=O)O)[C@H]([C@@H]([C@H]2O)O)O)O)O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O.N.N.N
• InChI: InChI=1S/C15H22N2O18P2.3H3N/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25;;;/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26);3*1H3/t4-,6-,7+,8+,9-,10-,11+,12-,14-;;;/m1.../s1
• InChIKey: MPPFPJYBGPJGKX-QWGSIYABSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid triamine
• IUPAC Traditional name: udp-α-D-glucuronic acid triamine
• Synonyms: UDP-GlcA; UDPGA; Uridine-diphosphate-glucuronic acid triammonium salt; Uridine[5′]diphospho[1]-α-D-glucopyranosuronic acid triammonium salt; Uridine 5′-diphosphoglucuronic acid triammonium salt

Database IDs

• CAS Number: 78132-48-6
• MDL Number: MFCD00077897
• Beilstein Number: 3645959
• PubChem SID: 162250466
• PubChem CID: 71312295

CALCULATED PROPERTIES

• Acid pKa: 1.716401
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): -11.289436
• LogD (pH = 7.4): -12.853641
• Log P: -4.6763334
• Molar Refractivity: 106.3232 cm^3
• Polarizability: 44.32593 Å^3
• Polar Surface Area: 308.61 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 23/24/25-36/37/38
• Safety Statements: 22-26-36-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (HPLC)
• Impurities: ≤3% solvent (ethanol); ≤7% water
• Linear Formula: C15H22N2O18P2 · 3NH3

DETAILS

Sigma Aldrich - 94337

Other Notes
Characterization of rat liver steroid UDP-glucuronosyl transferases1