(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-yl N-[2-(dimethylamino)ethyl]carbamate hydrochloride

• ChemBase ID: 132596
• Molecular Formular: C32H57ClN2O2
• Molecular Mass: 537.26018
• Monoisotopic Mass: 536.41085675
• SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2CC=C2[C@@]1(CC[C@@H](C2)OC(=O)NCCN(C)C)C)C.Cl
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)OC(=O)NCCN(C)C)C)C.Cl
• InChI: InChI=1S/C32H56N2O2.ClH/c1-22(2)9-8-10-23(3)27-13-14-28-26-12-11-24-21-25(36-30(35)33-19-20-34(6)7)15-17-31(24,4)29(26)16-18-32(27,28)5;/h11,22-23,25-29H,8-10,12-21H2,1-7H3,(H,33,35);1H/t23-,25+,26+,27-,28+,29+,31+,32-;/m1./s1
• InChIKey: ISXSJGHXHUZXNF-LXZPIJOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl N-[2-(dimethylamino)ethyl]carbamate hydrochloride
• IUPAC Traditional name: (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl N-[2-(dimethylamino)ethyl]carbamate hydrochloride
• Synonyms: 3β-[N-(Dimethylaminoethane)-carbamoyl]-cholesterol; DC-Chol; Cholesteryl 3β-N-(di-methyl-amino-ethyl)-carbamate hydrochloride

Database IDs

• CAS Number: 166023-21-8
• MDL Number: MFCD00467173
• PubChem SID: 162226873; 24892536
• PubChem CID: 16219102

CALCULATED PROPERTIES

• Acid pKa: 15.278586
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.577327
• LogD (pH = 7.4): 6.3264146
• Log P: 7.4627895
• Molar Refractivity: 151.3605 cm^3
• Polarizability: 59.96184 Å^3
• Polar Surface Area: 41.57 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~95%

DETAILS

Sigma Aldrich - C2832

Application
This cationic cholesterol derivative forms liposomes with L-α-phosphatidylethanolamine, dioleoyl, that efficiently transfect mammalian cell lines.