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Year of first isolation: |
1990 |
| Formula: | C19H28O5 |
| Molecular weight: | 336 |
| Occurence in plants: |
Lychnis flos-culculi [Caryophyllaceae] »  ![Wikipedia: Lychnis flos-culculi [Caryophyllaceae]](/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(CCC2O)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(CCC2O)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]2O)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]2O)O)C)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14R,17S)-2,3,14,17-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 19892-42-3 | | PubChem CID | 22213160 | InChiKey
[ ChemIDPlus: search ] | IHVPTRBJWKUCFE-QBCQSLFDSA-N | | InChI | InChI=1S/C19H28O5/c1-17-9-15(22)14(21)8-12(17)13(20)7-11-10(17)3-5-18(2)16(23)4-6-19(11,18)24/h7,10,12,14-16,21-24H,3-6,8-9H2,1-2H3/t10-,12-,14+,15-,16-,17+,18+,19+/m0/s1 |
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| CI-MS (NH3) m/z | 354 (MH+NH3)+, 337 (MH)+, 319, 303, 301 | | EI-MS m/z (relative intensity %) | | | HR-MS | | | FAB-MS m/z | 337 [M+H] (11), 319 [M+H-H2O] (5), 301 [M+H-2H2O] (4), |
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| CD3OD | | 01 | 37.40 | | 02 | 68.68 | | 03 | 68.48 | | 04 | 32.87 | | 05 | 51.88 | | 06 | 206.48 | | 07 | 121.59 | | 08 | 166.90 | | 09 | 35.46 | | 10 | 39.35 | | 11 | 21.34 | | 12 | 31.48 | | 13 | 48.27 | | 14 | 83.37 | | 15 | 29.05 (a) | | 16 | 29.74 (a) | | 17 | 79.24 | | 18 | 15.84 | | 19 | 24.45 | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | |
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| CD3OD | | 01-Ha | 1.44 (dd, 13.6, 4.4) | | 01-Hb | 1.80 (dd, 12.4, 3.3) | | 02-Ha | 3.83 (ddd, 13, 12) | | 03-He | 3.95 (bq, w1/2 = 3) | | 04-Ha | 1.73 | | 04-He | 1.68 | | 05-H | 2.39 (dd, 12.6, 4.8) | | 07-H | 5.78 (d, 2.5) | | 09-Ha | 3.15 (ddd, 11.3, 7.2) | | 11-Ha | 1.85 | | 11-He | 1.66 | | 12-Ha | 2.06 | | 12-He | 1.60 | | 15-Ha | 2.08 | | 15-Hb | 1.61 | | 16-Ha | 2.27 | | 16-Hb | 1.58 | | 17-H | 4.31 (dd, 9.3, 6.5) | | 18-Me | 0.71 (s ) | | 19-Me | 0.98 (s ) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3365 (OH), 1646 (CO) | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | GLC | | | HPLC | NP-HPLC, column Zorbax-Sil 250 mm x 4.6 mm i.d., flow-rate 1 ml.min-1 , solvent CH2Cl2-iPrOH-H2O (125:40:3) Ret 13.4 min (20E : 16.8 min); solvent CH2Cl2-iPrOH-H2O (125:25:2), Ret 22.0 min (20E 37.4 min); solvent cyclohexane-iPrOH-H2O (100:40:3), Ret 20.6 min (23.1 min for the 5beta isomer). |
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Drosophila melanogaster BII cell assay: EC50 = >10-5M | Drosophila melanogaster BII cell assay: EC50 = 8.6 x 10-5M |
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| Synthesis | HIKINO, H. et al. (1969) Tetrahedron 15, 3389-3394 |
 | | Synthesis | COCHRANE, J.S. et al. (1971) J. Chem. Soc., Chem. Commun. 3730-3732 |
| | First isolation | GIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 |
| | General | BÁTHORI, M. et al. (2000) Biomed. Chromatogr. 14, 464-467 |
| | Bioactivities | RAVI, M. et al. (2001) J. Chem. Inf. Comput. Sci. 41, 1587-1604 |
| | Identification | VOKÁČ, K. et al. (2002) Collect. Czech. Chem. Commun. 67, 124-139 |
| | Bioactivities | DINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 |
| | Bioactivities | HARMATHA, J. et al. (2008) Steroids 73, 466-471 |
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Permanent link to this datasheet: DIHYDRORUBROSTERONE
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