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

REPTANSLACTONE A

Year of first isolation: 2009
Formula:C29H44O8
Molecular weight:520
Occurence in plants:
Ajuga reptans var. reptans [Lamiaceae (alt. Labiatae)] » Images of Ajuga reptans var. reptans Wikipedia: Ajuga reptans var. reptans [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
REPTANSLACTONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCCC1C(C(=O)OC(C1O)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
CC[C@H]1[C@@H](C(=O)O[C@H]([C@@H]1O)[C@@](C)([C@H]2CC[C@@]3([C@@]2(CC[C@H]4C3=CC(=O)[C@H]5[C@@]4(C[C@@H]([C@@H](C5)O)O)C)C)O)O)C » JSMol: View in 3D
IUPAC Name(3S,4S,5R,6R)-4-ethyl-5-hydroxy-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-RN 
PubChem CID101477047
InChiKey
[ ChemIDPlus: search ]
WQUCWFQLILYXNA-HLLMZMHMSA-N
InChIInChI=1S/C29H44O8/c1-6-15-14(2)25(34)37-24(23(15)33)28(5,35)22-8-10-29(36)17-11-19(30)18-12-20(31)21(32)13-26(18,3)16(17)7-9-27(22,29)4/h11,14-16,18,20-24,31-33,35-36H,6-10,12-13H2,1-5H3/t14-,15-,16-,18-,20+,21-,22-,23+,24+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/zHR-ESIMS
ESI-MS m/z (relative intensity %)543 [M+Na]+ (41), 521 [M+H]+ (11), 505 [M-CH3]+ (11.5), 503 [M+H-H2O]+ (100), 484 [M-2H2O]+ (9), 452 [M+H-3H2O-CH3]+ (15), 437 (24), 413 (23), 391 (37.5), 365 (17)

CARBON NMR

PROTON NMR

CD3OD
0137.5
0268.8
0368.7
0433.05
0552.0
06206.7
07122.0
08168.6
0935.3
1039.4
1121.65
1232.5
1348.9
1485.3
1531.8
1621.9
1750.7
1818.6
1924.5
2077.5
2121.68
2272.8
2381.4
2448.9
2541.4
26182.3
2715.45
2821.4
2912.0
CD3OD
01-Ha1.42
01-He1.79
02-Ha3.85
03-He3.95
04-Ha1.70
04-He1.75
05-H2.38
07-H5.80
09-H3.16
11-Ha1.69
11-He1.80
12-Ha2.19
12-He1.87
15-Ha1.60
15-Hb1.97
16-Ha1.78
16-Hb2.00
17-H2.75
18-Me0.89
19-Me0.96
21-Me1.315 (s)
22-H3.59 (d, 9.8)
23-H4.40 (dd, 10.0, 2.5)
24-H2.11
25-H2.485 (qd, 7.5, 3.0)
27-Me1.29 (d, 7.6)
28-Ha1.27
28-Hb1.90
29-Me0.98 (t, 7.3)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25+17 ° (c 0.1; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)239.5 (3.931) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationVÁNYOLÓS, A. et al. (2009) J. Nat. Prod. 72, 929-932 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