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4-DEHYDRO-20-HYDROXYECDYSONE

Year of first isolation:	1995
Formula:	C₂₇H₄₂O₇
Molecular weight:	478
Occurence in plants:

Occurence in animals:
Parazoanthus sp [Zoanthidae] »

4-DEHYDRO-20-HYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILES	CC12CCC3C(=CC(=O)C4=CC(C(CC34C)O)O)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O
Isomeric SMILES [ PubChem: search \| XML ] [ ChemSpider: search ]	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)([C@@H](CCC(C)(C)O)O)O)O)C)C »
IUPAC Name	(2S,3R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,9,11,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN
PubChem CID	15225998
InChiKey [ ChemIDPlus: search ]	ZJTLBLRDHNVYKT-PUFKVNKUSA-N
InChI	InChI=1S/C27H42O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12-13,15,19-22,29-34H,6-11,14H2,1-5H3/t15-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH₃) m/z
EI-MS m/z (relative intensity %)
HR-FAB-MS	479.3014 (MH)⁺
FAB-MS (relative intensity %)	501 (M+Na)⁺ (7), 479 (MH)⁺ (8), 443 (MH-2H₂O)⁺ (5), 176 (90)

CARBON NMR

PROTON NMR

CD₃OD
01	38.1 (t )
02	68.2 (d )
03	67.5 (d )
04	130.2 (d )
05	146.7 (s )
06	192.8 (s )
07	124.4 (d )
08	169.5 (s )
09	44.6 (d )
10	40.3 (s )
11	21.8 (t )
12	32.3 (t )
13	48.6 (s )
14	85.2 (s )
15	31.8 (t )
16	21.4 (t )
17	50.6 (d )
18	18.0 (q )
19	22.6 (q )
20	78.0 (s )
21	21.0 (q )
22	78.4 (d )
23	27.3 (t )
24	42.4 (t )
25	71.3 (s )
26	28.9 (q )
27	29.7 (q )

CD₃OD
01-Ha	1.90 (m )
01-Hb	1.90 (m )
02-Ha	3.90 (dt, 8.8, 3.9)
03-He	4.18 (dd, 4.4, 3.9)
04-H	6.24 (d, 4.4)
07-H	5.95 (d, 2.4)
09-Ha	2.94 (ddd, 11.2, 7.3, 2.4)
11-Ha	1.72 (m )*
11-He	1.93 (m )*
12-Ha	1.85 (m )$
12-He	2.13 (td, 13.2, 4.9)$
15-Ha	1.60 (m )?
15-Hb	1.98 (m )?
16-Ha	1.72 (m )**
16-Hb	1.98 (m )**
17-H	2.37 (t, 8.8)
18-Me	0.91 (s )
19-Me	1.19 (s )
21-Me	1.19 (s )
22-H	3.31 (dd, 10.1, 1.0)
23-Ha	1.28 (m )
23-Hb	1.65 (m )
24-Ha	1.41 (ddd, 13.2, 11.5, 4.4)
24-Hb	1.78 (m )
26-Me	1.18 (s )
27-Me	1.20 (s )

PHYSICAL PROPERTIES

M.P.	236-238 °C (decomp) ;
[α]_D²⁰	- 33 ° (c 0.09; MeOH)
IR (KBr) ν _max (cm^-1)	3415 br, 2965, 2935, 1660, 1615, 1380, 1070
UV (EtOH) λ _max (log ε)	258 (3.968) ;

CHROMATOGRAPHY

HPTLC
TLC
GLC
HPLC	RP column Dynamax C₁₈, solvent MeOH-H₂O, 6:4 v/v

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 2.8 x 10-7M

REFERENCES

First isolation	SEARLE, P.A. et al. (1995) J. Nat. Prod. 58, 264-268
Bioactivities	DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207

Permanent link to this datasheet: 4-DEHYDRO-20-HYDROXYECDYSONE

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
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