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Year of first isolation: |
1982 |
| Formula: | C27H42O6 |
| Molecular weight: | 462 |
| Occurence in plants: |
Dacrydium pierrei [Podocarpaceae] »  ![Wikipedia: Dacrydium pierrei [Podocarpaceae]](/images/wikipedia.png)
Leuzea carthamoides [Asteraceae] »
Serratula coronata [Asteraceae] »
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| Occurence in animals: |
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![DACRYHAINANSTERONE [= 5-DEOXYKALADASTERONE]](images/ecdy/183.gif)
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| Canonical SMILES | CC(C)CCC(C(C)(C1CCC2(C1(CC=C3C2=CC(=O)C4C3(CC(C(C4)O)O)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=C1C2=CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,10S,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 13829647 | InChiKey
[ ChemIDPlus: search ] | HHSAPBUKXSETPT-ZTUUSGHWSA-N | | InChI | InChI=1S/C27H42O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h8,12,15,18,20-23,29-33H,6-7,9-11,13-14H2,1-5H3/t18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | 463 (MH)+, 445, 427, 361, 343, 325 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| CD3OD | | 01 | 36.2 | | 02 | 67.4 | | 03 | 66.9 | | 04 | 35.0 | | 05 | 50.2 | | 06 | 204.0 | | 07 | 117.8 | | 08 | 162.2 | | 09 | 145.0 | | 10 | 39.4 | | 11 | 132.4 | | 12 | 37.7 | | 13 | 47.0 | | 14 | 83.1 | | 15 | 30.0 | | 16 | 20.3 | | 17 | 49.1 | | 18 | 16.7 | | 19 | 30.0 | | 20 | 76.2 | | 21 | 19.3 | | 22 | 76.6 | | 23 | 29.1 | | 24 | 36.0 | | 25 | 27.8 | | 26 | 21.3 | | 27 | 21.9 |
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| CD3OD | | 01-Ha | 1.7 | | 01-Hb | 2.1 | | 02-Ha | 3.72 (m ) | | 03-He | 3.84 (m ) | | 04-Ha | 1.6 | | 04-He | 1.78 | | 05-H | 2.40 | | 07-H | 5.75 (br s, w1/2=4) | | 09-Ha | -- | | 11-Ha | 6.3 (ddd, 6.5, 2, 2) | | 11-He | -- | | 12-Ha | 2.72 (br d, 18) | | 12-He | 2.42 | | 15-Ha | | | 15-Hb | | | 16-Ha | 2.05 | | 16-Hb | 1.75 | | 17-H | 2.45 | | 18-Me | 0.89 (s ) | | 19-Me | 1.10 (s ) | | 21-Me | 1.18 (s ) | | 22-H | 3.33 (dd, 11, 2) | | 23-Ha | 1.35 | | 23-Hb | 1.55 | | 24-Ha | | | 24-Hb | | | 25-H | 1.55 | | 26-Me | 0.91 (d, 6.5) | | 27-Me | 0.94 (d, 6.5) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 298 (4.152), 235 (3.806) |
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| HPTLC | | | TLC | Rf 0.56 (EtOAc-MeOH-NH4OH 85:10:5); Rf 0.67 (CH2Cl2-EtOH 85:15). | | GLC | | | HPLC | Normal phase (Zorbax-Sil) Ret. 10.4 min (CH2Cl2-iPrOH-H2O, 125:25:2) |
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Drosophila melanogaster BII cell assay: EC50 = 5.2 x 10-9M |
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Permanent link to this datasheet: DACRYHAINANSTERONE [= 5-DEOXYKALADASTERONE]
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