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Year of first isolation: |
1970 |
| Formula: | C29H44O9 |
| Molecular weight: | 536 |
| Occurence in plants: |
Cyathula capitata [Amaranthaceae] »  ![Wikipedia: Cyathula capitata [Amaranthaceae]](/images/wikipedia.png)
Ajuga reptans [Lamiaceae (alt. Labiatae)] »
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| Occurence in animals: |
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| Canonical SMILES | CC1C(C(OC1=O)C)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5(C4(CC(C(C5)O)O)C)O)C)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)C[C@@H]1[C@H](OC(=O)[C@H]1C)C)O)O)C)O)C » 
| | IUPAC Name | (3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-6-oxo-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]butyl]-3,5-dimethyloxolan-2-one | | CAS-RN | | | PubChem CID | 12442769 | InChiKey
[ ChemIDPlus: search ] | YQCOGGGDJXBMBU-JIVHLSMOSA-N | | InChI | InChI=1S/C29H44O9/c1-14-16(15(2)38-24(14)34)10-22(32)27(5,35)21-7-9-28(36)18-11-23(33)29(37)13-20(31)19(30)12-26(29,4)17(18)6-8-25(21,28)3/h11,14-17,19-22,30-32,35-37H,6-10,12-13H2,1-5H3/t14-,15+,16-,17-,19-,20+,21-,22+,25+,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 518 (M-18)+ (4), 500 (10), 482 (4), 464 (2), 446 (1), 379 (2), 361 (14), 343 (24), 325 (17), 316 (9), 201 (M - 335) (5), 183 (8), 157 (M - 379) (18), 113 (13), 43 (100) | | MS (thermospray) m/z (relat. intensity %) | (MeOH:1M aq. HCO2NH4 3:7) 537 (M+H)+ (100), 536 (M)+ (80) |
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| CDCl3/CD3OD | | 01 | 34.5 | | 02 | 66.8 | | 03 | 68.4 | | 04 | 33.2 | | 05 | 78.4 | | 06 | 200.9 | | 07 | 118.6 | | 08 | 166.4 | | 09 | 37.3 | | 10 | 43.7 | | 11 | 43.7 | | 12 | 19.9 | | 13 | 30.8 | | 14 | 83.3 | | 15 | 30.8 | | 16 | 20.9 | | 17 | 48.5 | | 18 | 15.8 | | 19 | 16.7 | | 20 | 76.1 | | 21 | 19.3 | | 22 | 73.0 | | 23 | 32.8 | | 24 | 47.8 | | 25 | 42.0 | | 26 | 180.1 | | 27 | 14.9 | | 28 | 80.3 | | 29 | 18.7 |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 5.27 | | 03-He | 4.10 | | 04-Ha | | | 04-He | | | 07-H | 6.20 (d, 2) | | 09-Ha | 3.58 (ddd ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.21 | | 19-Me | 1.13 | | 21-Me | 1.56 | | 22-H | 4.99 (dd ) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | -- | | 27-Me | 1.36 (d, 7) | | 28-CH(Me)- | 4.11 (dq 7,6) | | 29-Me | 1.34 (d, 6) |
| CDCl3 (tri-OAc) | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | 5.22 | | 04-Ha | | | 04-He | | | 07-H | 5.95 (d 2) | | 09-Ha | 3.21 (ddd 2.8,10) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.85 (s ) | | 19-Me | 0.93 (s ) | | 21-Me | 1.25 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | | | 27-Me | 1.28 (d ) | | 28-CH(Me)- | | | 29-Me | 1.41 (d ) |
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| M.P. | 159-161 °C | | [α]D20 | + 39.6° (c 0.69, pyridine) | | IR (KBr) ν max (cm-1) | 3425 (OH), 1748 (?-lactone), 1670 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 241 (4.01) |
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| HPTLC | | | TLC | Rf 0.15 (AcOEt-MeOH 10:1) (20E : 0.13); Rf 0.31 (CHCl3-MeOH 5:1) (20E 0.16) | | GLC | | | HPLC | RP-HPLC, Column Spherisorb 5ODS2, 125x10 mm, flow-rate 3 ml.min-1, solvent iPrOH-H2O 9:91, 50°C. |
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Drosophila melanogaster BII cell assay: EC50 = 9.0 x 10-8M | Sarcophaga assay: active |
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| First isolation | HIKINO, H. et al. (1969) Tetrahedron Lett. (18), 1417-1420 |
 | | General | HIKINO, H. et al. (1970) Tetrahedron 26, 887-898 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | CALGANO, M.P. et al. (1995) An. Quim. 90, 483-486 |
| | Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
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Permanent link to this datasheet: SENGOSTERONE
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