|
|
|
|
Year of first isolation: |
1971 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Achyranthes fauriei [Amaranthaceae] »  ![Wikipedia: Achyranthes fauriei [Amaranthaceae]](/images/wikipedia.png)
Leuzea carthamoides [Asteraceae] »
Silene italica ssp. nemoralis [Caryophyllaceae] »
|
| Occurence in animals: |
|
|
|
![(5α)-20-HYDROXYECDYSONE [= EPIECDYSTERONE]](images/ecdy/310.gif)
| |
| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5S,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 11784921 | InChiKey
[ ChemIDPlus: search ] | NKDFYOWSKOHCCO-RWWVMDEUSA-N | | InChI | InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17+,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1 |
| |
| HR-MS | 481.2829 [M+H]+, required 481.3165 | | FAB-MS m/z (relative intensity %) | 503 (5) [M+Na]+, 481 (100) [M+H]+, 463 (51), 445 (84), 427 (38), 363 (12), 347 (24), 329 (28), 301 (21), 277 (39), 257 (49), 215 (46). |
|
|
| CD3OD | | 01 | 43.86 | | 02 | 70.30 | | 03 | 72.68 | | 04 | 24.71 | | 05 | 55.29 | | 06 | 203.00 | | 07 | 123.57 | | 08 | 166.23 | | 09 | 48.26 | | 10 | 39.23 | | 11 | 21.41 | | 12 | 32.42 | | 13 | ~49.0 | | 14 | 85.02 | | 15 | 31.86 | | 16 | 21.67 | | 17 | 50.59 | | 18 | 17.98 | | 19 | 15.72 | | 20 | 77.94 | | 21 | 21.02 | | 22 | 78.44 | | 23 | 27.34 | | 24 | 42.41 | | 25 | 71.31 | | 26 | 29.67 | | 27 | 28.96 |
|
| CD3OD | | 01-Hb | 2.09 (dd 14.4, 3.3) | | 01-He | 1.54 (dd 14.4, 3.2) | | 02-Ha | 3.96 (dq 4.6, 3.3, 3.2) | | 03-He | 3.58 (ddd 4.6, 3.2, ~12) | | 04-Ha | 1.90 (m 13.2, 4.5, 3.2) | | 04-He | 1.75 (q 13.2, ~12) | | 05-H | 2.38 (dd 4.5, ~12) | | 07-H | 5.84 (d 2.7) | | 09-Ha | 2.72 (ddd 7.4, ~11) | | 11-Ha | ~1.66 | | 11-He | ~1.77 | | 12-Ha | 2.11 (dt) | | 12-He | 1.84 (dd) | | 15-Ha | 1.95 | | 15-Hb | 1.58 | | 16-Ha | 1.71 | | 16-Hb | 1.97 | | 17-H | 2.37 (m | | 18-Me | 0.88 (s) | | 19-Me | 1.02 (s) | | 21-Me | 1.19 (s) | | 22-H | 3.34 (dd 1.7, ~11) | | 23-Ha | 1.66 | | 23-Hb | 1.28 | | 24-Ha | 1.78 | | 24-Hb | 1.43 | | 26-Me | 1.20 (s) | | 27-Me | 1.19 (s) |
|
| |
| M.P. | 278 °C | | [α]D20 | +56.2 ° (c 0.13 ; MeOH) | | IR (KBr) ν max (cm-1) | 3422 (OH), 1651 (C=O; KBr) | | UV (EtOH) λ max (log ε) | |
| |
| |
Drosophila melanogaster BII cell assay: EC50 = 3.3 x 10-6M |
| |
| |
Permanent link to this datasheet: (5α)-20-HYDROXYECDYSONE [= EPIECDYSTERONE]
|
|
