Welcome to online ecdysteroids database ! . .
Access data · History · Contact

CHEILANTHONE B

Year of first isolation: 1970
Formula:C27H46O5
Molecular weight:450
Occurence in plants:
Cheilanthes tenuifolia [Pteridaceae] » Images of Cheilanthes tenuifolia Wikipedia: Cheilanthes tenuifolia [Pteridaceae]
Cheilanthes mysurensis [Pteridaceae] » Images of Cheilanthes mysurensis Wikipedia: Cheilanthes mysurensis [Pteridaceae]
Occurence in animals:
 
CHEILANTHONE B

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)C1CCC2(C1(CCC3C2CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)CC1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(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[C@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(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[C@@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)C)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,8R,9S,10R,13R,14R,17R)-2,3,14-trihydroxy-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN26130-75-6
PubChem CID101297732
InChiKey
[ ChemIDPlus: search ]
ZQJLJTBAWSHGIA-XHCKOWILSA-N
InChIInChI=1S/C27H46O5/c1-15(2)6-7-21(28)16(3)17-9-11-27(32)19-12-22(29)20-13-23(30)24(31)14-25(20,4)18(19)8-10-26(17,27)5/h15-21,23-24,28,30-32H,6-14H2,1-5H3/t16-,17+,18-,19+,20-,21+,23+,24-,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)450(M)+ (2.5), 432 (M -18)+(9.5), 417 (1), 414 (M -2x18)+(7), 399 (1.5), 396 (M -3x18)+(1), 381 (0.5), 350 (M - C22-C27)+(3.5), 332 (M-C22-C27-18)+ (21), 302 (M-C20-C27)+ (25), 101 (5.5), 83 (61), 69 (57), 55 (100).
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 
C5D5N
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-Ha 
07-Hb 
08-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.85 (s )
19-Me1.03 (s )
21-Me1.24 (d, 6)
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me0.84 (d, 6)
27-Me0.84 (d, 6)
CDCl3 (2,3,22-triOAc)
01-Ha 
01-Hb 
02-Ha5.38 (w1/2 = 8)
03-He~ 4.9
04-Ha 
04-He 
05-H 
07-Ha 
07-Hb 
08-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.81
19-Me~ 0.95
21-Me~ 0.95
22-H~ 4.9
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me0.90 (d, 6)
27-Me0.90 (d, 6)
acetates2.01, 2.05, 2.10

PHYSICAL PROPERTIES

M.P.225-228 °C(or 230°-235°C)
[α]D20-25.9 ° (c ; MeOH)
IR (KBr) ν max (cm-1)3636 (OH), 1684 (or 1704 ?) (carbonyl)
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silica, Rf 0.50 (CHCl3 - 96% EtOH 4:1) (ecdysone 0.20)
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 1.3 x 10-7M

REFERENCES

First isolationFAUX, A. et al. (1970) Chem. Commun., 243-244 Search more
GeneralTHANU IYER, R. et al. (1973) Indian J. Chem. 11, 1338-1338 Search more
BioactivitiesDINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 Search more

see Important notice
© 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
designed by Cybersales a.s.
Powered by Cybersales
PRINTER READY | MEDIUM | WIDE