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Year of first isolation: |
1995 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Vitex pinnata [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Vitex pinnata [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
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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)(CCC(C(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@@](CCC(C(C)(C)O)O)(C)O)O)C)C » 
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@@](CC[C@H](C(C)(C)O)O)(C)O)O)C)C »
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@@](CC[C@@H](C(C)(C)O)O)(C)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2S)-2,5,6-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 | 15214617 | InChiKey
[ ChemIDPlus: search ] | VUBCOFCCIFBERZ-MRHAYEGBSA-N | | InChI | InChI=1S/C27H44O7/c1-23(2,32)22(31)8-10-26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-9-25(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 |
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| CI-MS (NH3) m/z | 481 [M+H]+ (7), 463 [M+H-H2O]+ (45), 445 [M+H-2H2O]+ (82),427 [M+H-3H2O]+ (81), 143 [C8H13O3-H2O]+ (100) | | EI-MS m/z (relative intensity %) | 444 [M-2H2O]+ (2), 426 (1), 385 (2), 363 (1), 327 (3), 309 (1), 301 (5), 283 (1), 161 (4) 143 (100), 125 (22), 117 (3), 107 (10), 99 (3), 89 (2), 81 (7), 71 (20), 59 (13) | | HR-MS | |
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| C5D5N | | 01 | 37.6 | | 02 | 68.0 | | 03 | 67.9 | | 04 | 32.3 | | 05 | 51.2 | | 06 | 201.5 | | 07 | 121.5 | | 08 | 166.3 | | 09 | 34.2 | | 10 | 38.8 | | 11 | 20.9 | | 12 | 31.7 | | 13 | 47.4 | | 14 | 84.3 | | 15 | 31.4 | | 16 | 21.9 | | 17 | 53.6 | | 18 | 17.8 | | 19 | 24.3 | | 20 | 74.2 | | 21 | 27.0 | | 22 | 42.3 | | 23 | 26.6 | | 24 | 79.8 | | 25 | 72.7 | | 26 | 25.9 | | 27 | 25.8 |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.19 (br ddd, 12, 4, 4) | | 03-He | 4.26 (br s ) | | 04-Ha | | | 04-He | | | 05-H | 3.04 (dd, 13, 4) | | 07-H | 6.26 (d, 2.5) | | 09-Ha | 3.61 (ddd, 11.5, 7.5, 2) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.93 (t, 9) | | 18-Me | 1.17 (s ) | | 19-Me | 1.09 (s ) | | 21-Me | 1.61 (s ) | | 22-Ha | | | 22-Hb | | | 23-Ha | | | 23-Hb | | | 24-H | 3.77 (bb dd, 10, 3) | | 26-Me | 1.47 (s ) | | 27-Me | 1.51 (s ) |
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| M.P. | 198-200 °C | | [α]D25 | + 41.2 ° (c 0.199; MeOH) | | IR (KBr) ν max (cm-1) | 3400 (OH), 1640 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 242 (4.02) |
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Drosophila melanogaster BII cell assay: EC50 = 4.0 x 10-7M | Musca assay: 2% (20-hydroxyecdysone = 100%) |
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| First isolation | SUKSAMRARN, A. et al. (1993) Phytochemistry 32, 303-306 |
 | | Bioactivities | SUKSAMRARN, A. et al. (2002) Insect Biochem. Molec. Biol. 32, 193-197 |
| | Bioactivities | DINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 |
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Permanent link to this datasheet: PINNATASTERONE
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