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AJUGASTERONE D

Year of first isolation: 1980
Formula:C27H42O7
Molecular weight:478
Occurence in plants:
Ajuga nipponensis [Lamiaceae (alt. Labiatae)] » Images of Ajuga nipponensis Wikipedia: Ajuga nipponensis [Lamiaceae (alt. Labiatae)]
Polypodium vulgare [Polypodiaceae] » Images of Polypodium vulgare Wikipedia: Polypodium vulgare [Polypodiaceae]
Occurence in animals:
 
AJUGASTERONE D

STRUCTURE DESCRIPTORS

Canonical SMILESCC1(CCC(O1)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5(C4(CC(C(C5)O)O)C)O)C)O)O)C
Isomeric SMILES
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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)(C1CCC(O1)(C)C)O)O)C)O)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]1CCC(O1)(C)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]1CCC(O1)(C)C)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,13R,14S,17S)-17-[(1R)-1-(5,5-dimethyloxolan-2-yl)-1-hydroxyethyl]-2,3,5,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID21123579
InChiKey
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UVQAWEDRKUWQCJ-DJLNXEJJSA-N
InChIInChI=1S/C27H42O7/c1-22(2)9-8-21(34-22)25(5,31)19-7-11-26(32)16-12-20(30)27(33)14-18(29)17(28)13-24(27,4)15(16)6-10-23(19,26)3/h12,15,17-19,21,28-29,31-33H,6-11,13-14H2,1-5H3/t15-,17-,18+,19-,21?,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)479 (MH)+, 443, 379 (M-C22-C27), 361, 343, 325, 143 (C20-C27), 125, 99 (C22-C27), 81
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
0134.4
0268.6
0370.4
0436.3
0580.4
06202.5
07120.7
08167.7
0939.2
1045.5
1122.6
1232.5
1348.4
1485.2
1531.8
1621.9
1751.9
1818.3
1917.1
2077.1
2120.8
2285.7
2328.6
2439.8
2581.8
2628.5
2729.1
C5D5N
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-He 
07-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.94 (s )
19-Me1.04 (s )
21-Me1.28 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.10 (s )
27-Me1.10 (s )
CD3OD
01-Ha1.73
01-Hb1.73
02-Ha3.94
03-He3.99
04-Ha2.07
04-He1.77
05-H 
07-H5.85
09-Ha3.19
11-Ha1.75
11-He1.81
12-Ha2.15
12-He1.86
15-Ha1.60
15-Hb1.96
16-Ha1.81
16-Hb2.00
17-H2.36
18-Me0.85
19-Me0.91
20-H 
21-Me1.21
22-H3.91
23-Ha1.75
23-Hb1.89
24-Ha1.75
24-Hb1.75
26-Me1.24
27-Me1.25

PHYSICAL PROPERTIES

M.P.234-237 °C
[α]D20 
IR (KBr) ν max (cm-1)3400, 1690
UV (EtOH) λ max (log ε)244-246 (4.07)

CHROMATOGRAPHY

HPTLC 
TLCRf 0.71 NP-TLC on silica (CHCl3-EtOH 5:1) (20E 0.32); Rf 0.32 NP-TLC on silica (CHCl3-EtOH 4:1)
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationCHOU, W.S. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam pp. 281-297 Search more
IdentificationSIMON, A. et al. (2011) Steroids 76, 1419-1424 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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