Synonym
Serratinine; Decahydro-1,4-dihydroxy-2-methyl-5H,9H,12H-indeno(7a,1-h)indolizin-12-one.
IUPAC/Chemical Name
(1S,2S,7aR,9aR,13aR)-1-hydroxy-2-methyl-12-oxodecahydro-1H,8H-indeno[7a,1-h]indolizine 4(5H)-oxide
InChi Key
GXXCLFHDZZGIQG-VUGSXULSSA-N
InChi Code
InChI=1S/C16H25NO3/c1-11-10-17(20)8-2-6-15(17)7-5-12-3-4-13(18)9-16(12,15)14(11)19/h11-12,14,19H,2-10H2,1H3/t11-,12-,14-,15-,16-,17-/m0/s1
SMILES Code
C1CC[N@@]2(C[C@@H]([C@@H]([C@@]34[C@@]12CC[C@@H]3CCC(C4)=O)O)C)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
279.38
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
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2: Zhang J, Wu J, Hong B, Ai W, Wang X, Li H, Lei X. Diversity-oriented synthesis of Lycopodium alkaloids inspired by the hidden functional group pairing pattern. Nat Commun. 2014 Aug 1;5:4614. doi: 10.1038/ncomms5614. PubMed PMID: 25082077.
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5: Katakawa K, Kitajima M, Aimi N, Seki H, Yamaguchi K, Furihata K, Harayama T, Takayama H. Structure elucidation and synthesis of lycoposerramine-B, a novel oxime-containing Lycopodium alkaloid from Lycopodium serratum Thunb. J Org Chem. 2005 Jan 21;70(2):658-63. PubMed PMID: 15651814.
6: Morita H, Kobayashi J. A biomimetic transformation of serratinine into serratezomine A through a modified Polonovski reaction. J Org Chem. 2002 Jul 26;67(15):5378-81. PubMed PMID: 12126432.
7: Inubushi Y, Ishi H, Yasui B, Harayama T. [Structures of rearrangement products derived from serratinine derivatives (author's transl)]. Yakugaku Zasshi. 1974 Sep;94(9):1077-80. Japanese. PubMed PMID: 4476775.
