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Year of first isolation: |
1966 |
| Formula: | C27H44O6 |
| Molecular weight: | 464 |
| Occurence in plants: |
Taxus cuspidata [Taxaceae] »  ![Wikipedia: Taxus cuspidata [Taxaceae]](/images/wikipedia.png)
various Ferns [Gymnosperms] »
Tapinella panuoides [Fungi] »
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| Occurence in animals: |
Gecarcinus lateralis [Gecarcinidae] »
Callinectes sapidus [Portunidae] »
Carcinus maenas [Crustaceae] »
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| Canonical SMILES | CC(C)CCC(C(C)(C1CCC2(C1(CCC3C2=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=C1[C@@H]2CC[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,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-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 | 13408-56-5 | | PubChem CID | 115127 | InChiKey
[ ChemIDPlus: search ] | PJYYBCXMCWDUAZ-JJJZTNILSA-N | | InChI | InChI=1S/C27H44O6/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/h12,15-16,18,20-23,29-33H,6-11,13-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | 482 (MH+NH3)+, 465 (M+H)+, 447, 429, 411, 363, 345, 327 | | EI-MS m/z (relative intensity %) | 344 (40), 300 (42), 83 (25), 18 (100) | | HR-MS | |
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| C5D5N | | 01 | 37.9 | | 02 | 68.0 | | 03 | 68.0 | | 04 | 32.4 | | 05 | 51.3 | | 06 | 203.5 | | 07 | 121.7 | | 08 | 166.0 | | 09 | 34.4 | | 10 | 38.7 | | 11 | 21.4 | | 12 | 31.8 | | 13 | 48.1 * | | 14 | 84.1 | | 15 | 31.9 | | 16 | 21.4 | | 17 | 50.0 | | 18 | 17.9 | | 19 | 24.4 | | 20 | 76.7 | | 21 | 21.1 | | 22 | 76.7 | | 23 | 30.2 | | 24 | 37.1 | | 25 | 28.1 | | 26 | 22.3 | | 27 | 23.3 |
| CD3OD | | 01 | 37.37 | | 02 | 68.73 | | 03 | 68.51 | | 04 | 32.88 | | 05 | 51.80 | | 06 | 206.50 | | 07 | 122.14 | | 08 | 168.00 | | 09 | 35.11 | | 10 | 39.26 | | 11 | 21.51 | | 12 | 32.53 | | 13 | * | | 14 | 85.25 | | 15 | 31.77 | | 16 | 21.51 | | 17 | 50.48 | | 18 | 18.02 | | 19 | 24.39 | | 20 | 77.86 | | 21 | 20.98 | | 22 | 77.99 | | 23 | 37.66 | | 24 | 30.48 | | 25 | 29.23 | | 26 | 22.74 | | 27 | 23.41 |
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| CD3OD | | 01-Ha | 1.43 (dd, 13.2, 12.4) | | 01-He | 1.79 (dd, 13.2, 4.5) | | 02-Ha | 3.82 (ddd, 12.0, 4.0, 3.4) | | 03-He | 3.94 (q ) | | 04-Ha | 1.70 | | 04-He | 1.74 | | 05-H | 2.38 (dd, 12.8, 4.6) | | 07-H | 5.81 (d, 2.6) | | 09-Ha | 3.15 (ddd, 10.5, 7.0, 2.6) | | 11-Ha | 1.81 | | 11-He | 1.70 | | 12-Ha | 2.12 (dt, 13.0, 13.0, 5.0) | | 12-He | 1.88 (ddd, 12.8, 4.2, 2.0) | | 15-Ha | 1.96 | | 15-Hb | 1.59 | | 16-Ha | 1.99 | | 16-Hb | 1.70 | | 17-H | 2.37 (t, 8.8, 8.8) | | 18-Me | 0.890 (s ) | | 19-Me | 0.967 (s ) | | 21-Me | 1.175 (s ) | | 22-Hb | 3.33 (dd, 10.0, 1.7) | | 23-Ha | 1.47 | | 24-Ha | 1.46 | | 24-Hb | 1.21 | | 25-H | 1.56 | | 26-Me | 0.924 (d, 6.5) | | 27-Me | 0.915 (d, 6.5) |
| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | | | 18-Me 0.89 | 1.16 | | 19-Me | | | 19-Me 0.96 | 1.03 | | 21-Me | | | 21-Me 1.17 | 1.51 | | 22-Hb | | | 23-Ha | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | | | 26-Me 0.92 | 0.82 (d, 6) | | 27-Me | | | 27-Me 0.91 | 0.82 (d, 6) |
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| M.P. | 259-260°C (decomp.) | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3420 (OH), 1643 (CO) | | UV (MeOH) λ max (log ε) | 244 (4.093), 326 (2.11) |
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| HPTLC | | | TLC | NP-TLC on silicagel Rf 0.42 (CHCl3-EtOH 4:1); RP-TLC on paraffin coated silica gel Rf 0.19 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.21 (MeOH-H2O 65:35) | | GLC | GLC Ret 4.4 min on 1.5% OV101 (0.9 m x 4.5 mm i.d.) at 285°C after silylation at 140°C | | HPLC | RP-HPLC-RP, Ultrasphere-ODS (15 cm x 4.6 mm) MeOH-H2O, gradient 40 to 80% MeOH over 20 min, retention volume 17.2 ml (20E 9.4 ml). |
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Drosophila melanogaster BII cell assay: EC50 = 3.1 x 10-10M | Drosophila melanogaster BII cell assay: EC50 = 2.0 x 10-10M | Calliphora vicina imaginal disc assay: EC50 = 1.4 x 10-9M | Drosophila melanogaster imaginal disc assay: EC50 = 1.0 x 10-9M | Drosophila melanogaster Kc-H cell assay: EC50 = 1.8 x 10-9M | Galleria mellonella in vivo assay: ED50 = 12.5 ug/g | Sarcophaga bullata in vivo assay: ED50 = 7.3 ug/g | Dermestes vulpinus in vivo assay: ED50 = 17.0 ug/g | Calliphora assay: 100% (20-hydroxyecdysone = 100%) |
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| First isolation | NAKANISHI, K. et al. (1966) J. Chem. Soc., Chem. Commun. 915-917 |
 | | General | TAKEMOTO, T. et al. (1967) Chem. Pharm. Bull. 15, 1816 |
| | General | IMAI, S. et al. (1967) Steroids 10, 557-565 |
| | General | TAKEMOTO, T. et al. (1968) Yakugaku Zasshi 88, 359 |
| | First isolation | McCARTHY, J.F. et al. (1979) Steroids 34, 799-806 |
| | Bioactivities | YUND, M.A. et al. (1980) In: Invert. Systems in Vitro pp. 229-237 |
| | Bioactivities | CHERBAS, L. et al. (1980) W. Roux Arch. Devel. Biol. 189, 1-15 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | LACHAISE, F. et al. (1981) Hoppe-Seyler´s Z. Physiol. Chem. 521-529 |
| | General | WILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 |
| | General | BIELBY, C.R. et al. (1986) J. Chromatogr. 351, 57-64 |
| | Bioactivities | CLEMENT, C.Y. et al. (1993) Insect Biochem. Molec. Biol. 23, 187-193 |
| | Bioactivities | TERENTIOU, P. et al. (1993) Insect Biochem. Molec. Biol. 23, 131-136 |
| | Bioactivities | SLÁMA, K. et al. (1993) Insect Biochem. Molec. Biol. 23, 181-185 |
| | General | MINGSHEN, L. et al. (1998) Chin. J. Magn. Resonance 15, 539-542 |
| | Identification | VOKÁČ, K. et al. (1998) Phytochemistry 49, 2109-2114 |
| | 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: PONASTERONE A
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