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PRECYASTERONE

Year of first isolation: 1970
Formula:C29H44O8
Molecular weight:520
Occurence in plants:
Cyathula capitata [Amaranthaceae] » Images of Cyathula capitata Wikipedia: <br />
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Occurence in animals:
 
PRECYASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1C(CC(OC1=O)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C(C)O
Isomeric SMILES
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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]1OC(=O)C(C(C1)C(C)O)C)O)O)C)C  » JSMol: View in 3D
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]1OC(=O)[C@@H]([C@@H](C1)C(C)O)C)O)O)C)C  » JSMol: View in 3D
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]1OC(=O)[C@H]([C@@H](C1)C(C)O)C)O)O)C)C  » JSMol: View in 3D
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]1OC(=O)[C@@H]([C@H](C1)C(C)O)C)O)O)C)C  » JSMol: View in 3D
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]1OC(=O)[C@H]([C@H](C1)C(C)O)C)O)O)C)C » JSMol: View in 3D
IUPAC Name(3S,4S,6R)-4-[(1R)-1-hydroxyethyl]-6-[(1R)-1-hydroxy-1-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-3-methyloxan-2-one
CAS-RN27335-85-9
PubChem CID102004875
InChiKey
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RPCTUYZLPGGPJD-YSEUJXISSA-N
InChIInChI=1S/C29H44O8/c1-14-16(15(2)30)10-24(37-25(14)34)28(5,35)23-7-9-29(36)18-11-20(31)19-12-21(32)22(33)13-26(19,3)17(18)6-8-27(23,29)4/h11,14-17,19,21-24,30,32-33,35-36H,6-10,12-13H2,1-5H3/t14-,15+,16-,17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)502 (M-18)+, 363, 345, 327, 157, 139, 121
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
28 
29 
CDCl3 (tri0Ac)
01-Ha 
02-Ha5.01 (ddd )
03-He5.33 (ddd )
04-Ha 
04-He 
05-H 
07-H5.88 (d )
09-Ha3.12 (ddd )
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.87 (s )
19-Me1,03 (s )
21-Me1.24 (s )
22-H4.18 (dd )
23-Ha 
24-Ha 
24-Hb 
26-Me--
27-Me1.28 (d )
28-H5.11 (dq )
29-Me1.27 (d )
C5D5N (free form)
01-Ha 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H6.16 (d )
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.11 (s )
19-Me1.05 (s )
21-Me1.44 (s )
22-H 
23-Ha 
24-Ha 
24-Hb 
26-Me--
27-Me1.35 (d )
28-H 
29-Me1.24 (d )

PHYSICAL PROPERTIES

M.P. 
[α]D20+39 ° (c ; MeOH)
IR (KBr) ν max (cm-1)1710 (?-lactone), 1650 (cyclohexenone)
UV (EtOH) λ max (log ε)244 (?)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationHIKINO, H. et al. (1970) Chem. Pharm. Bull. 18, 1078-1080 Search more

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© Université Pierre & Marie Curie, Paris 6, France
© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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