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Year of first isolation: |
1994 |
| Formula: | C29H46O7 |
| Molecular weight: | 506 |
| Occurence in plants: |
Leuzea carthamoides [Asteraceae] »  ![Wikipedia: Leuzea carthamoides [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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![24(241)[Z]-DEHYDROAMARASTERONE B](images/ecdy/108.gif)
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| Canonical SMILES | CC(C)C(=CCO)CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | CC(C)/C(=C\CO)/C[C@H]([C@@](C)([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)O)O » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(Z,2R,3R)-2,3,7-trihydroxy-5-propan-2-ylhept-5-en-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101851584 | InChiKey
[ ChemIDPlus: search ] | JHBBUAIBYMEEGM-HIGSQXFKSA-N | | InChI | 1S/C29H46O7/c1-16(2)17(8-11-30)12-25(34)28(5,35)24-7-10-29(36)19-13-21(31)20-14-22(32)23(33)15-26(20,3)18(19)6-9-27(24,29)4/h8,13,16,18,20,22-25,30,32-36H,6-7,9-12,14-15H2,1-5H3/b17-8-/t18-,20-,22+,23-,24-,25+,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | 524 (M+H+ NH3)+, 507 (M+H)+, 489 (M+H-H2O)+, 471(M+H-2H2O)+, 453 (M+H-3H2O)+, 380 (524 - C22--C29)+, 363 (M+H - C22--C29)+, 345 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| D2O | | 01 | 36.4 | | 02 | 68.3 | | 03 | 68.2 | | 04 | 32.3 | | 05 | 51.4 | | 06 | 209.3 | | 07 | 122.1 | | 08 | | | 09 | 34.9 | | 10 | 39.1 | | 11 | 21.0 | | 12 | 32.0 | | 13 | 48.5 | | 14 | 86.3 | | 15 | 31.2 | | 16 | 21.0 | | 17 | 50.2 | | 18 | 18.1 | | 19 | 24.2 | | 20 | 79.0 | | 21 | 20.6 | | 22 | 75.7 | | 23 | 34.7 | | 24 | 147.4 | | 25 | 30.4 | | 26 | 21.7 | | 27 | 22.2 | | 28 | 124.3 | | 29 | 58.7 |
| CD3OD | | 01 | 37.36 | | 02 | 68.70 | | 03 | 68.50 | | 04 | 32.86 | | 05 | 51.78 | | 06 | 206.44 | | 07 | 122.11 | | 08 | 167.95 | | 09 | 35.09 | | 10 | 39.24 | | 11 | 21.53 | | 12 | 32.49 | | 13 | 48.56 | | 14 | 85.20 | | 15 | 31.75 | | 16 | 21.71 | | 17 | 50.46 | | 18 | 18.05 | | 19 | 24.41 | | 20 | 77.79 | | 21 | 21.01 | | 22 | 75.94 | | 23 | 34.71 | | 24 | 145.75 | | 25 | 30.73 | | 26 | 18.41 | | 27 | 21.87 | | 28 | 125.95 | | 29 | 58.91 |
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| D2O | | 01-Ha | 1.4 (t, 13) | | 01-He | 1.85 | | 02-Ha | 3.99 (m, w1/2 = 22) | | 03-He | 4.07 (m, w1/2 = 8) | | 04-Ha | 1.75 | | 04-He | 1.75 | | 05-H | 2.34 (t ) | | 07-H | 5.99 (d, 2.5) | | 09-Ha | 3.11 (m, w1/2 = 22) | | 11-Ha | 1.75 | | 11-He | 1.85 | | 12-Ha | 1.73 | | 12-He | 1.95 | | 15-Ha | 1.65 | | 15-Hb | 2.05 (m) | | 16-Ha | 1.95 | | 16-Hb | 1.85 | | 17-H | 2.39 (t ) | | 18-Me | 0.88 (s ) | | 19-Me | 1.00 (s ) | | 21-Me | 1.27 (s ) | | 22-H | 3.72 (d, 10) | | 23-Ha | 2.41 | | 23-Hb | 1.95 | | 25-H | 2.87 (sp, 6.6) | | 26-Me | 1.04 (d, 6.6) | | 27-Me | 1.04 (d, 6.6) | | 28-H | 5.45 (t, 7, X) | | 29-Ha/Hb | 4.23 (m, AB) |
| CD3OD | | 01-Ha | 1.43 (dd, 13.2, 11.8) | | 01-He | 1.80 (dd, 13.2, 4.2) | | 02-Ha | 3.84 (ddd, 11.8, 4.2, 3.0) | | 03-He | 3.95 (q, 3, 3, 3) | | 04-Ha | 1.69-1.76 | | 04-He | 1.69-1.76 | | 05-H | 2.38 (dd, 12.6, 4.6) | | 07-H | 5.81 (d, 2.5) | | 09-Ha | 3.16 (ddd, 11, 7, 2.5) | | 11-Ha | 1.71 | | 11-He | 1.82 | | 12-Ha | 2.14 | | 12-He | 1.88 | | 15-Ha | 1.97 | | 15-Hb | 1.62 | | 16-Ha | 1.78 | | 16-Hb | 2.03 | | 17-H | 2.43 (dd, 9.6, 8.3 ) | | 18-Me | 0.898 (s ) | | 19-Me | 0.970 (s ) | | 21-Me | 1.218 (s ) | | 22-H | 3.60 (dd, 10.6, 1.5) | | 23-Ha | 2.30 | | 23-Hb | 1.86 | | 25-H | 2.85 (6x 6.8) | | 26-Me | 1.049 (d, 6.8) | | 27-Me | 1.049 (d, 6.8) | | 28-H | 5.46 (bt, 6.7, 6.7) | | 29-Ha/Hb | 4.17 (d, 6.7) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 243 (?) |
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Drosophila melanogaster BII cell assay: EC50 = 5.5 x 10-7M |
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Permanent link to this datasheet: 24(241)[Z]-DEHYDROAMARASTERONE B
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