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24-EPI-PINNATASTERONE

Year of first isolation: 2002
Formula:C27H44O7
Molecular weight:480
Occurence in plants:
Vitex scabra [Lamiaceae] » Images of Vitex scabra Wikipedia: <br />
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Occurence in animals:
 
24-EPI-PINNATASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(CCC(C(C)(C)O)O)O)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
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)(CCC(C(C)(C)O)O)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)(CC[C@H](C(C)(C)O)O)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)(CC[C@@H](C(C)(C)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2S)-2,5,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID15214617
InChiKey
[ ChemIDPlus: search ]
VUBCOFCCIFBERZ-MRHAYEGBSA-N
InChIInChI=1S/C27H44O7/c1-23(2,32)22(31)8-10-26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-9-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22?,24+,25+,26-,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
HR-FABMS (negative ion mode)479.3001 [M-H]- (calc. for C27H43O7 479.3008)
CI-MS (NH3) m/z

CARBON NMR

PROTON NMR

C5D5N
0137.7
0268.0
0367.9
0432.3
0551.3
06203.6
07121.6
08166.3
0934.2
1038.5
1120.9
1231.7
1347.4
1484.3
1531.4
1621.8
1753.5
1817.8
1924.2
2074.4
2126.8
2242.6
2326.8
2479.9
2572.7
2625.9
2725.7
C5D5N
01-Ha 
01-Hb 
02-Ha4.15 (m)
03-He4.23 (br s )
04-Ha 
04-He 
05-H2.96 (dd, 13.1, 3.6)
07-H6.19 (d, 2.1)
09-Ha3.56 (m)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 2.90 (t, 9.3) 
18-Me 1.08 (s ) 
19-Me1.00 (s )
21-Me 1.55 (s ) 
22-Ha 
22-Hb 
23-Ha 
23-Hb 
24-H3.76 (br d, 8.8)
26-Me 1.42 (s ) 
27-Me1.46 (s )

PHYSICAL PROPERTIES

M.P.
[α]D25
IR (KBr) ν max (cm-1)3422 (OH), 2929, 1648 (cyclohexenone), 1384, 1057
UV (EtOH) λ max (log ε)

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSUKSAMRARN, A. et al. (2002) J. Nat. Prod. 65, 1690-1692 Search more

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