(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxy-N-{3-[(4R)-N-{3-[(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanamido]propyl}-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanamido]propyl}hexanamide

• ChemBase ID: 132116
• Molecular Formular: C42H75N3O16
• Molecular Mass: 878.0554
• Monoisotopic Mass: 877.51473334
• SMILES: C[C@H](CCC(=O)N(CCCNC(=O)[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)CCCNC(=O)[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]1[C@H]2[C@@H](C[C@H]2[C@@]1(CC[C@H](C2)O)C)O)O)C
• Canonical SMILES: OC[C@H]([C@H]([C@@H]([C@H](C(=O)NCCCN(C(=O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)C[C@H]1[C@H]2[C@H](O)C[C@H]2[C@]1(C)CC[C@H](C2)O)C)CCCNC(=O)[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C42H75N3O16/c1-21(24-7-8-25-32-26(18-30(52)42(24,25)3)41(2)11-10-23(48)16-22(41)17-27(32)49)6-9-31(53)45(14-4-12-43-39(60)37(58)35(56)33(54)28(50)19-46)15-5-13-44-40(61)38(59)36(57)34(55)29(51)20-47/h21-30,32-38,46-52,54-59H,4-20H2,1-3H3,(H,43,60)(H,44,61)/t21-,22+,23-,24-,25+,26+,27-,28-,29-,30+,32+,33-,34-,35+,36+,37-,38-,41+,42-/m1/s1
• InChIKey: ZWEVPYNPHSPIFU-AUGHYPCGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxy-N-{3-[(4R)-N-{3-[(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanamido]propyl}-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]propyl}hexanamide
• IUPAC Traditional name: (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxy-N-{3-[(4R)-N-{3-[(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanamido]propyl}-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanamido]propyl}hexanamide
• Synonyms: (3α,5β,7α,12α)-N,N-Bis[3-(D-gluconoylamino)propyl]-3,7,12-trihydroxy-cholan-24-amide; BigCHAP; N,N-Bis[3-D-gluconamidopropyl]cholamide; N,N-Bis[3-D-gluconamidopropyl]cholamide (Ultra Pure); N,N-Bis[3-(D-gluconamido)propyl]cholamide; BigCHAP

Database IDs

• CAS Number: 86303-22-2
• MDL Number: MFCD00082541
• PubChem SID: 162226393
• PubChem CID: 9919170

CALCULATED PROPERTIES

• Acid pKa: 11.701898
• H Acceptors: 16
• H Donor: 15
• LogD (pH = 5.5): -6.0862484
• LogD (pH = 7.4): -6.08627
• Log P: -6.086248
• Molar Refractivity: 218.1775 cm^3
• Polarizability: 87.18531 Å^3
• Polar Surface Area: 341.5 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 110-112°C; 136-145°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Toxic (T)
• German water hazard class: 1
• Risk Statements: 61-20/21-36/37/38
• Safety Statements: 53-22-36/37/39-45
• Storage Temperature: 2-8°C

Product Information

• Purity: ~98%
• Description: non-ionic

DETAILS

Sigma Aldrich - B9518

Application
Useful in solubilization of functional opiate receptor.

Toronto Research Chemicals - B438500

Homogeneous nonionic detergent with bile acid hydrophobic group. Useful in solubilization of functional opiate receptor.

Toronto Research Chemicals - B438501

Homogeneous nonionic detergent with bile acid hydrophobic group. Useful in solubilization of functional opiate receptor.

REFERENCES

• Hjelmeland, L.M., et al.: Anal. Biochem., 130, 485 (1983)
• Buhler, H., et al.: Biochim. et Biophys. Acta., 1075, 206 (1991)
• Hjelmeland, L.M., et al.: Anal. Biochem., 130, 485 (1983)
• Buhler, H., et al.: Biochim. et Biophys. Acta., 1075, 206 (1991)