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Year of first isolation: |
1970 |
| Formula: | C27H42O6 |
| Molecular weight: | 462 |
| Occurence in plants: |
Stachyurus praecox [Stachyuraceae] »  ![Wikipedia: Stachyurus praecox [Stachyuraceae]](/images/wikipedia.png)
Serratula wolffii [Asteraceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1=CCC2C(C)(C(CCC(C)(C)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(C1=CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,17S)-2,3-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,9,11,12,16,17-decahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | 30655-79-9 | | PubChem CID | 15922525 | InChiKey
[ ChemIDPlus: search ] | ZYXLMHXQZHELAP-SVJUWISJSA-N | | InChI | InChI=1S/C27H42O6/c1-24(2,32)10-9-23(31)27(5,33)22-7-6-16-15-12-19(28)18-13-20(29)21(30)14-26(18,4)17(15)8-11-25(16,22)3/h6,12,17-18,20-23,29-33H,7-11,13-14H2,1-5H3/t17-,18-,20+,21-,22-,23+,25-,26+,27+/m0/s1 |
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| EI-MS m/z (relative intensity %) | 462 (M)+; 444 (M - 18)+, 345 (M- C22-C27)+ (5), 327 (7), 99 (C22-C27)+ (86), 81 (45), 43 (100). | | HR-MS | 444.2861 (for C27H40O5, calc. 444.2815) | | LSI-MS (negative) m/z | (% RI): 553 (3) [M+glyc-H]-, 461 (8) [M-H]-, 183 (100) |
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| D2O | | 01 | 37.7 | | 02 | 69.8 | | 03 | 69.9 | | 04 | 33.7 | | 05 | 52.7 | | 06 | | | 07 | 122.0 | | 08 | | | 09 | 41.0 | | 10 | 41.5 | | 11 | | | 12 | 41.8 | | 13 | 50.2 | | 14 | 152.0 | | 15 | 133.1 | | 16 | 31.8 | | 17 | 59.5 | | 18 | 21.8 | | 19 | 25.4 | | 20 | 80.0 | | 21 | 21.06 | | 22 | 80.0 | | 23 | 28.4 | | 24 | 43.0 | | 25 | 74.4 | | 26 | 30.0 | | 27 | 30.9 |
| CD3OD | | 01 | 37.2 | | 02 | 68.71 | | 03 | 68.67 | | 04 | 33.0 | | 05 | 51.6 | | 06 | 205.9 | | 07 | 121.2 | | 08 | 158.9 | | 09 | 39.96 | | 10 | 40.06 | | 11 | 21.8 | | 12 | 41.2 | | 13 | 49.1 | | 14 | 150.8 | | 15 | 130.4 | | 16 | 32.1 | | 17 | 59.1 | | 18 | 20.2 | | 19 | 24.15 | | 20 | 77.3 | | 21 | 20.5 | | 22 | 78.7 | | 23 | 27.4 | | 24 | 42.4 | | 25 | 71.4 | | 26 | 29.0 | | 27 | 30.0 |
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| CD3OD | | 01-Ha | 1.465 | | 01-He | 1.81 | | 02-Ha | 3.80 | | 03-He | 3.94 | | 04-Ha | 1.65 | | 04-He | 1.72 | | 05-H | 2.385 | | 07-H | 6.08 | | 09-Ha | 2.72 | | 11-Ha | 1.86 | | 11-He | 1.79 | | 12-Ha | 1.64 | | 12-Hb | 2.31 | | 15-H | 6.08 | | 16-Ha | 2.25 | | 16-Hb | 2.625 | | 17-H | 2.20 | | 18-Me | 1.14 | | 19-Me | 0.97 | | 21-Me | 1.25 | | 22-H | 3.335 | | 23-Ha | 1.32 | | 23-Hb | 1.61 | | 24-Ha | 1.425 | | 24-Hb | 1.81 | | 26-Me | 1.185 | | 27-Me | 1.21 |
| D2O | | 01-Ha | 1.41 (t 13.4) | | 01-He | 1.88 | | 02-Ha | 3.95 (dt 11.7, 3.5) | | 03-He | 4.05 (bm w1/2 =8) | | 04-Ha | 1.72 | | 04-He | 1.77 | | 05-H | 2.32 | | 07-H | 6.23 (bs w1/2 =6.3) | | 09-Ha | 2.77 (bm w1/2 =23) | | 11-Ha | 1.80 | | 11-He | 1.87 | | 12-Ha | 1.62 | | 12-He | 2.31 | | 15-H | 6.23 (bs w1/2 =6.3) | | 16-Ha | 2.53 (dd 16, 11) | | 16-Hb | 2.30 (dd 16, 8) | | 17-H | 2.24 (dd 11, 8) | | 18-Me | 1.10 (s) | | 19-Me | 1.00 (s) | | 21-Me | 1.28 (s) | | 22-H | 3.44 (dd 10.6, 1.4) | | 23-Ha | 1.34 | | 23-Hb | 1.62 | | 24-Ha | 1.50 (td 13, 3.5) | | 24-Hb | 1.78 | | 26-Me | 1.21 (s) | | 27-Me | 1.23 (s) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3400 (OH), 1640 (cyclohexenone), 1590 | | UV (EtOH) λ max (log ε) | 298 (4.107) |
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Drosophila melanogaster BII cell assay: EC50 = 8.2 x 10-8M |
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Permanent link to this datasheet: STACHYSTERONE B
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