(2S,3S,4S,5R,6S)-6-[(6-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; cyclohexanamine

• ChemBase ID: 155920
• Molecular Formular: C20H27ClN2O7
• Molecular Mass: 442.89058
• Monoisotopic Mass: 442.15067889
• SMILES: c1cc2c(cc1Cl)[nH]cc2O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O)O.C1CCC(CC1)N
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](Oc2c[nH]c3c2ccc(c3)Cl)[C@@H]([C@H]([C@@H]1O)O)O.NC1CCCCC1
• InChI: InChI=1S/C14H14ClNO7.C6H13N/c15-5-1-2-6-7(3-5)16-4-8(6)22-14-11(19)9(17)10(18)12(23-14)13(20)21;7-6-4-2-1-3-5-6/h1-4,9-12,14,16-19H,(H,20,21);6H,1-5,7H2/t9-,10-,11+,12-,14+;/m0./s1
• InChIKey: CGXWVPSZSVEFAI-CYRSAHDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(6-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; cyclohexanamine
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(6-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; cyclohexylamine
• Synonyms: Rose-glucuronide CHA salt; Salmon-glucuronide CHA salt; 6-Chloro-3-indolyl-β-D-glucuronide cyclohexylammonium salt

Database IDs

• CAS Number: 138182-20-4
• MDL Number: MFCD00153940
• PubChem SID: 162250058; 24854974
• PubChem CID: 16211694

CALCULATED PROPERTIES

• Acid pKa: 3.376503
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.6853322
• LogD (pH = 7.4): -2.9840488
• Log P: 0.4246936
• Molar Refractivity: 75.942 cm^3
• Polarizability: 31.647455 Å^3
• Polar Surface Area: 132.24 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -70.5±2°, c = 1% in DMF/H2O 1:1

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C14H14ClNO7 · C6H13N

DETAILS

Sigma Aldrich - 24907

Other Notes
Sales restrictions may apply