(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[7-(phenylcarbamoyl)heptanamido]oxy}oxane-2-carboxylic acid

• ChemBase ID: 177898
• Molecular Formular: C20H28N2O9
• Molecular Mass: 440.44432
• Monoisotopic Mass: 440.17948049
• SMILES: O([C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)O)NC(=O)CCCCCCC(=O)Nc1ccccc1
• Canonical SMILES: O=C(NO[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)CCCCCCC(=O)Nc1ccccc1
• InChI: InChI=1S/C20H28N2O9/c23-13(21-12-8-4-3-5-9-12)10-6-1-2-7-11-14(24)22-31-20-17(27)15(25)16(26)18(30-20)19(28)29/h3-5,8-9,15-18,20,25-27H,1-2,6-7,10-11H2,(H,21,23)(H,22,24)(H,28,29)/t15-,16-,17+,18-,20-/m0/s1
• InChIKey: AGXZHORDQQELAH-JNIAIEOXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[7-(phenylcarbamoyl)heptanamido]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[7-(phenylcarbamoyl)heptanamido]oxy}oxane-2-carboxylic acid
• Synonyms: 1-O-[[1,8-Dioxo-8-(phenylamino)octyl]amino]-β-D-glucopyranuronic Acid; Vorinostat glucuronide; Suberoylanilide Hydroxamic Acid β-D-Glucuronide

Database IDs

• CAS Number: 863456-50-2
• PubChem SID: 164233808
• PubChem CID: 44425383

CALCULATED PROPERTIES

• Acid pKa: 3.281102
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -1.9125556
• LogD (pH = 7.4): -3.1437109
• Log P: 0.28824237
• Molar Refractivity: 105.8169 cm^3
• Polarizability: 41.780537 Å^3
• Polar Surface Area: 174.65 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 188-190°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S688710

The metabolite (MI) of Suberoylanilide Hydroxamic Acid.

REFERENCES

• Sun, W.S., et al.: J. Med. Chem., 46, 5619 (2003)