Properties of Rapamycin
Rapamycin is a macrolide antibiotic with immunosuppressant properties. The physical properties of rapamycin are diplayed in the table below:
|
Names |
Rapamycin, sirolimus, Rapamune,
1,18-dihydroxy-12- |
|
Chemical formula |
C51H79NO13 |
|
Molecular weight |
914.18 |
|
Melting Point |
183-185 C |
|
CAS Registry Number |
53123-88-9 |
|
Beilstein Registry Number |
604010 |
Optical Rotatory Power
Type [alpha]
Optical Rotatory Power -58.2 deg
Wavelength 589 nm
Temperature 25 C
(Source of information: Beilstein)
1H and 13C NMR assignments2
In CDCl3 rapamycin exists as a mixture of conformers in a 3:1 ratio, which complicates the NMR spectrum. In the table below the chemical shifts of the carbons and hydrogens of the major isomer only are given.
|
Carbon No. |
Carbon Type |
Major carbon |
Major proton |
Carbon No. |
Carbon Type |
Major carbon |
Major proton |
|
1
|
C=O |
169.2 |
-
|
28
|
CH-OH |
77.3 |
4.17 |
|
2
|
CH |
51.3 |
5.29 |
29
|
C=C |
136.1 |
-
|
|
3
|
CH2 |
27.0 |
2.34, 1.76 |
30
|
CH=C |
126.8 |
5.42 |
|
4
|
CH2 |
20.6 |
1.78, 1.47 |
31
|
CH |
46.6 |
3.33 |
|
5
|
CH2 |
25.3 |
1.75, 1.48 |
32
|
C=O |
208.2 |
-
|
|
6
|
CH2 |
44.2 |
3.59, 3.44 |
33
|
CH2 |
40.7 |
2.74, 2.60 |
|
8
|
C=O |
166.8 |
-
|
34
|
CH-OCO |
75.7 |
5.17 |
|
9
|
C=O |
192.5 |
-
|
35
|
CH |
33.1 |
1.98 |
|
10
|
O-C-OH |
98.5 |
-
|
36
|
CH2 |
38.4 |
1.22, 1.12 |
|
11
|
CH |
33.7 |
1.98 |
37
|
CH |
33.2 |
1.39 |
|
12
|
CH2 |
27.3 |
1.60, 1.60 |
38
|
CH2 |
34.2 |
2.10, 0.68 |
|
13
|
CH2 |
31.3 |
1.62, 1.33 |
39
|
CH-OCH3 |
84.4 |
2.93 |
|
14
|
67.2 |
3.86 |
40
|
CH-OH |
73.9 |
3.37 |
|
|
15
|
CH2 |
38.8 |
1.85, 1.52 |
41
|
CH2 |
31.3 |
1.99, 1.33 |
|
16
|
CH-OCH3 |
84.4 |
3.67 |
42
|
CH2 |
31.7 |
1.70, 1.00 |
|
17
|
C=C |
135.5 |
-
|
43
|
11-CH3 |
16.2 |
0.95 |
|
18
|
CH=C |
129.6 |
5.97 |
44
|
17-CH3 |
10.2 |
1.65 |
|
19
|
CH=C |
126.4 |
6.39 |
45
|
23-CH3 |
21.5 |
1.05 |
|
20
|
CH=C |
133.6 |
6.32 |
46
|
25-CH3 |
13.8 |
1.00 |
|
21
|
CH=C |
130.1 |
6.15 |
47
|
29-CH3 |
13.0 |
1.74 |
|
22
|
CH=C |
140.2 |
5.54 |
48
|
31-CH3 |
16.0 |
1.11 |
|
23
|
CH |
35.2 |
2.32 |
49
|
35-CH3 |
15.9 |
0.92 |
|
24
|
CH2 |
40.2 |
1.50, 1.20 |
50
|
16-OCH3 |
55.8 |
3.13 |
|
25
|
CH |
41.4 |
2.74 |
51
|
27-OCH3 |
59.5 |
3.34 |
|
26
|
C=O |
215.6 |
-
|
52
|
39-OCH3 |
56.5 |
3.41 |
|
27
|
CH-OCH3 |
84.9 |
3.71 |
For information on cancer tumour activity of rapamycin see:
http://dtp.nci.nih.gov/docs/static_pages/compounds/226080.html