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DIPLOCLIDINE

Year of first isolation: 2003
Formula:C27H37O4N
Molecular weight:439
Occurence in plants:
Diploclisia glaucescens [Menispermaceae] » Images of Diploclisia glaucescens Wikipedia: Diploclisia glaucescens [Menispermaceae]
Occurence in animals:
 
DIPLOCLIDINE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1=C2CCC3(C2=C(CC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)N=C1CCC(C)(C)O)C
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2Cc2c3[C@@]1(CCc3c(c(n2)CCC(C)(C)O)C)C)C » JSMol: View in 3D
IUPAC Name(1R,5R,7R,8S,10R,11R)-7,8-dihydroxy-15-(3-hydroxy-3-methylbutyl)-1,10,16-trimethyl-14-azapentacyclo[11.6.1.02,11.05,10.017,20]icosa-2,13(20),14,16-tetraen-4-one
CAS-RN 
PubChem CID101262935
InChiKey
[ ChemIDPlus: search ]
ULPGFWCVEISNKT-VNLCIVOGSA-N
InChIInChI=1S/C27H37NO4/c1-14-15-6-9-26(4)17-11-21(29)18-12-22(30)23(31)13-27(18,5)16(17)10-20(24(15)26)28-19(14)7-8-25(2,3)32/h11,16,18,22-23,30-32H,6-10,12-13H2,1-5H3/t16-,18-,22+,23-,26+,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
FAB-HR-MS440.2837 [M+H, C27H38O4N requires 440.2801]
FAB-MS m/z440 [MH] +

CARBON NMR

PROTON NMR

CDCl3
0136.9
0267.6
0367.4
0431.1
0549.3
06202.0
07123.5
08171.7
0940.8
1040.3
1121.4
12158.6
13136.6
1447.1
1540.1
1631.9
17142.0
1826.3
1922.6
20130.2
2122.1
22155.2
2322.9
2444.4
2570.9
2627.6
2730.4
CDCl3
01-Ha1.66 (dd, 13.7, 12.0)
01-He1.94 (dd, 13.7, 3.8)
02-Ha3.73 (ddd, 12.0, 3.8, 2.5)
03-He4.04 (ddd, 2.5)
04-Ha1.59 (ddd, 14.2, 13.4, 2.5)
04-He1.89 (dt, 14.2, 4.5, 2.5)
05-H2.48 (dd, 13.4, 4.5)
07-H6.04 (d, 2.7)
09-H2.67 (m)
11-Ha2.42 (dd, 14.4, 13.0)
11-He3.24 (dd (14.4, 4.0)
15-Ha2.12 (ddd 12.4, 11.0, 8.6)
15-Hb2.40 (dd 12.4, 7.0)
16-Ha2.86 (dd 16.5, 8.6)
16-Hb3.20 (ddd 16.5, 11.0, 7.0)
18-Me1.31 (s)
19-Me1.07 (s)
20-H-
21-Me2.57 (s)
22-H-
23-Ha2.72 (td 12.5, 5.9)
23-Hb2.92 (ddd 13.0, 12.5, 2.8)
24-Ha1.35 (m)
24-Hb1.77 (td 13.0, 5.9)
25-H-
26-Me1.37 (s)
27-Me1.33 (s)

PHYSICAL PROPERTIES

M.P.- °C ;
[α]D20? ° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)215, 230, 275 (-) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationJAYASINGHE, U.L.B et al. (2003) Tetrahedron Lett. 44, 8769-8771 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
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