[(2S,3R,4S,5R)-5-hydroxy-2-{[(3R,4S,5R,6R)-6-hydroxy-4,5-bis(sulfooxy)oxan-3-yl]oxy}-3-(sulfooxy)oxan-4-yl]oxidanesulfonic acid

• ChemBase ID: 568
• Molecular Formular: C10H18O21S4
• Molecular Mass: 602.49732
• Monoisotopic Mass: 601.9223416
• SMILES: S(=O)(=O)(O[C@H]1[C@H](O[C@@H]2OC[C@@H](O)[C@H](OS(=O)(=O)O)[C@H]2OS(=O)(=O)O)CO[C@@H](O)[C@@H]1OS(=O)(=O)O)O
• Canonical SMILES: O[C@@H]1CO[C@H]([C@@H]([C@H]1OS(=O)(=O)O)OS(=O)(=O)O)O[C@@H]1CO[C@H]([C@@H]([C@H]1OS(=O)(=O)O)OS(=O)(=O)O)O
• InChI: InChI=1S/C10H18O21S4/c11-3-1-26-10(8(31-35(22,23)24)5(3)28-32(13,14)15)27-4-2-25-9(12)7(30-34(19,20)21)6(4)29-33(16,17)18/h3-12H,1-2H2,(H,13,14,15)(H,16,17,18)(H,19,20,21)(H,22,23,24)/t3-,4-,5+,6+,7-,8-,9-,10+/m1/s1
• InChIKey: FCCNSUIJIOOXEZ-SJYYZXOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S,3R,4S,5R)-5-hydroxy-2-{[(3R,4S,5R,6R)-6-hydroxy-4,5-bis(sulfooxy)oxan-3-yl]oxy}-3-(sulfooxy)oxan-4-yl]oxidanesulfonic acid
• IUPAC Traditional name: [(2S,3R,4S,5R)-5-hydroxy-2-{[(3R,4S,5R,6R)-6-hydroxy-4,5-bis(sulfooxy)oxan-3-yl]oxy}-3-(sulfooxy)oxan-4-yl]oxidanesulfonic acid
• Brand Name: Elmiron
• Synonyms: Pentosan Polysulfate

Database IDs

• CAS Number: 37300-21-3
• PubChem SID: 46509187; 160964031
• PubChem CID: 37720

CALCULATED PROPERTIES

JChem

• Acid pKa: -2.9445777
• H Acceptors: 17
• H Donor: 6
• LogD (pH = 5.5): -12.728352
• LogD (pH = 7.4): -12.72841
• Log P: -11.399326
• Molar Refractivity: 96.3789 cm^3
• Polarizability: 44.08261 Å^3
• Polar Surface Area: 322.55 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.49
• LOG S: -2.24
• Solubility (Water): 3.49e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -8

DETAILS

DrugBank - DB00686

• Drug Groups: approved
• Description: A sulfated pentosyl polysaccharide with heparin-like properties. [PubChem]
• Indication: For the relief of bladder pain or discomfort associated with interstitial cystitis.
• Pharmacology: Pentosan polysulfate sodium is a low molecular weight heparin-like compound. It has anticoagulant and fibrinolytic effects.
• Affected Organisms: Humans and other mammals
• Absorption: Slow
• Half Life: 4.8 hours
• External Links: RxList