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Year of first isolation: |
2010 |
| Formula: | C28H42O6 |
| Molecular weight: | 474 |
| Occurence in plants: |
Sagina japonica Ohwi (Caryophyllaceae) [Fungus] »  ![Wikipedia: Sagina japonica Ohwi (Caryophyllaceae) [Fungus]](/images/wikipedia.png)
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| Occurence in animals: |
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![JAPONICONE [= 24-METHYLENESHIDASTERONE]](images/ecdy/485.gif)
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| Canonical SMILES | CC1(C(=C)CC(O1)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C | 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)(C1OC(C(=C)C1)(C)C)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-17-[(1R)-1-[(2R)-5,5-dimethyl-4-methylideneoxolan-2-yl]-1-hydroxyethyl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101431681 | InChiKey
[ ChemIDPlus: search ] | IPJLOFDOKBDRGY-IJYGRGDZSA-N | | InChI | InChI=1S/C28H42O6/c1-15-11-23(34-24(15,2)3)27(6,32)22-8-10-28(33)17-12-19(29)18-13-20(30)21(31)14-25(18,4)16(17)7-9-26(22,28)5/h12,16,18,20-23,30-33H,1,7-11,13-14H2,2-6H3/t16-,18-,20+,21-,22-,23+,25+,26+,27+,28+/m0/s1 |
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| FAB-MS m/z (relative intensity %) | 473 [M-H] (100), 455 [M-H2O] (10), 361 (20), 318 (18), 125 (15) | | EI-MS m/z (relative intensity %) | negative | | HR-ESI-MS | 497.2959 [M+Na]+, calculated 497.2936 for C28H42O6Na |
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| C5D5N | | 01 | 38.68 (t) | | 02 | 68.16 (d) | | 03 | 68.11 (d) | | 04 | 32.49 (t) | | 05 | 51.47 (s) | | 06 | 203.36 (s) | | 07 | 121.74 (d) | | 08 | 165.96 (s) | | 09 | 34.50 (d) | | 10 | 38.04 (s) | | 11 | 21.78 (t) | | 12 | 31.73 (t) | | 13 | 47.63 (s) | | 14 | 84.21 (s) | | 15 | 32.49 (t) | | 16 | 21.05 (t) | | 17 | 51.41 (d) | | 18 | 17.94 (q) | | 19 | 24.45 (q) | | 20 | 75.23 (s) | | 21 | 21.05 (q) | | 22 | 81.84 (d) | | 23 | 34.85 (d) | | 24 | 157.67 (s) | | 25 | 81.84 (s) | | 26 | 28.92 (q) | | 27 | 27.68 (q) | | 28 | 103.42 (t) |
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| C5D5N | | 01-Ha | 1.92 (m) | | 01-He | 2.10 (m) | | 02-Ha | 4.17 (br, s) | | 03-He | 4.11 (br, d) | | 04-Ha | 2.14 (m) | | 04-He | 2.67 (m) | | 05-H | 3.02 (dd, 2.24, 11.03) | | 07-H | 6.25 (br, s) | | 09-H | 3.61 (t, 10.24) | | 11-Ha | 1.75 (m) | | 11-He | 1.91 (m) | | 12-Ha | 1.92 (m) | | 12-He | 2.08 (m) | | 14-OH | 6.36 (s) | | 15-Ha | 1.94 (m) | | 15-Hb | 2.13 (m) | | 16-Ha | 2.10 (m) | | 16-Hb | 2.25 (m) | | 17-H | 2.92 (t, 7.21) | | 18-Me | 1.04 (s) | | 19-Me | 1.41 (s) | | 21-Me | 1.07 (s) | | 22-H | 4.09 (m) | | 23-Ha | 2.48 (m) | | 23-Hb | 2.64 (m) | | 26-Me | 1.38 (s) | | 27-Me | 1.32 (s) | | 28-CH2 | 4.81 (s), 4.87 (s) |
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| M.P. | 231-232 °C ; | | [α]D18 | + 75.8 ° (c 0.13; MeOH) ; different from 24-methyleneshidasterone (isomeric?) | | IR (KBr) ν max (cm-1) | 3427, 2930, 1645 (CO), 1059 (OH), 879 (RCH=CH2) | | UV (MeOH) λ max (log ε) | 224 (1.32) ; |
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| LC | Sephadex LH20, RP-18, MCI-gel CHP 20P eluted with MeOH-H2O (45-80%) | | HPLC | | | GLC | | | TLC | |
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Permanent link to this datasheet: JAPONICONE [= 24-METHYLENESHIDASTERONE]
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