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SCABRASTERONE

Year of first isolation: 2002
Formula:C27H44O7
Molecular weight:480
Occurence in plants:
Vitex scabra [Lamiaceae (alt. Labiatae)] » Images of Vitex scabra Wikipedia: Vitex scabra [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
SCABRASTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CC(C3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(CCCC(C)(C)O)O)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)(CCCC(C)(C)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,11R,13R,14S,17S)-17-[(2R)-2,6-dihydroxy-6-methylheptan-2-yl]-2,3,11,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101218681
InChiKey
[ ChemIDPlus: search ]
ZETXKEIWBPSFMF-PPUARKICSA-N
InChIInChI=1S/C27H44O7/c1-23(2,32)8-6-9-26(5,33)21-7-10-27(34)16-12-17(28)15-11-18(29)19(30)13-24(15,3)22(16)20(31)14-25(21,27)4/h12,15,18-22,29-34H,6-11,13-14H2,1-5H3/t15-,18+,19-,20+,21-,22+,24-,25+,26+,27+/m0/s1

MASS SPECTRUM

ES-MS m/z (positive ion mode)503 [M+Na]+ (100)
EI-MS m/z (relative intensity %)
HR-MS (negative mode)479.3011 [M-H] - (calculated for C27H43O7, 479.3008)

CARBON NMR

PROTON NMR

C5D5N
0139.6
0268.3
0368.0
0432.8
0552.7
06204.1
07122.0
08164.5
0942.6
1039.4
1168.8
1243.8
1347.5
1484.4
1531.5
1619.5
1753.2
1818.7
1924.7
2074.2
2126.7
2245.4
2321.8
2445.6
2569.6
2629.6
2729.8
C5D5N
01-Ha 
01-He 
02-Ha4.56 (m)
03-He4.21 (m, w1/2 = 7)
04-Ha 
04-He 
05-H3.00 (dd, 13.1, 3.6)
07-H6.26 (d, 2.1)
09-H3.84 (dd, 8.5, 2.1)
11-H4.56 (m)
12-Ha2.99 (m)
12-He2.65 (dd, 11.9, 5.8)
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.93 (t, 9)
18-Me1.18 (s)
19-Me1.29 (s)
21-Me1.53 (s)
22-Ha 
22-Hb 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.33 (s)
27-Me1.33 (s)

PHYSICAL PROPERTIES

M.P.- °C ;
[α]D20? ° (c ; MeOH)
IR (KBr) ν max (cm-1)3422, 2925, 1654, 1384
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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© 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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