(4R)-N-[3-(dimethylamino)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]pentanamide

• ChemBase ID: 164043
• Molecular Formular: C29H52N2O4
• Molecular Mass: 492.73418
• Monoisotopic Mass: 492.39270815
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H]([C@@H](C2)O)[C@H]2[C@]([C@H](C1)O)([C@H](CC2)[C@@H](CCC(=O)NCCCN(C)C)C)C)C)O
• Canonical SMILES: CN(CCCNC(=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)C
• InChI: InChI=1S/C29H52N2O4/c1-18(7-10-26(35)30-13-6-14-31(4)5)21-8-9-22-27-23(17-25(34)29(21,22)3)28(2)12-11-20(32)15-19(28)16-24(27)33/h18-25,27,32-34H,6-17H2,1-5H3,(H,30,35)/t18-,19+,20-,21-,22+,23+,24-,25+,27+,28+,29-/m1/s1
• InChIKey: CLOVEIUMHBMREZ-JSAKOLFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-N-[3-(dimethylamino)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]pentanamide
• IUPAC Traditional name: (4R)-N-[3-(dimethylamino)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]pentanamide
• Synonyms: (3,5,7,12)-N-[3-(Dimethylamino)propyl]-3,7,12-trihydroxy-cholan-24-amide; 3-(Cholamidopropyl)-1,1-dimethamine

Database IDs

• CAS Number: 76555-98-1
• PubChem SID: 162258178
• PubChem CID: 46780965

CALCULATED PROPERTIES

• Acid pKa: 15.976543
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.3460237
• LogD (pH = 7.4): 0.08517858
• Log P: 1.9778322
• Molar Refractivity: 140.3927 cm^3
• Polarizability: 55.81866 Å^3
• Polar Surface Area: 93.03 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: White to Off-White Solid
• Melting Point: 167-170°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C292425

Useful as antidiabetic agents and inhibitors of phospholipase A2.

REFERENCES

• Hirose, K., et al.: J. Incl. Phenom. Macrocycl. Chem., 39, 193 (2001)
• Kral, V., et al.: Org. Biomol. Chem., 2, 1169 (2004)