IUPAC/Chemical Name
(2S,5R)-2-[(1R,4R,4aS,8aR)-4-isocyano-4,7-dimethyl-2,3,4a,5,6,8a-hexahydro-1H-naphthalen-1-yl]-5-(2-isocyanopropan-2-yl)-2-methyloxolane
InChi Key
WSPJFMZOFNQTAT-NBIPDHRESA-N
InChi Code
InChI=1S/C22H32N2O/c1-15-8-9-17-16(14-15)18(10-12-21(17,4)24-7)22(5)13-11-19(25-22)20(2,3)23-6/h14,16-19H,8-13H2,1-5H3/t16-,17+,18-,19-,21-,22+/m1/s1
SMILES Code
CC1=C[C@H]2[C@@H](CC[C@@](C)([N+]#[C-])[C@H]2CC1)[C@]3(C)CC[C@@H](O3)C(C)(C)[N+]#[C-]
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
340.51
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 |
1: Marine Isonitriles and Their Related Compounds Jens Emsermann, Ulrich Kauhl, Till Opatz Mar Drugs. 2016 Jan; 14(1): 16. Published online 2016 Jan 14. doi: 10.3390/md14010016 PMCID: PMC4728513
2: Syntheses and Biological Studies of Marine Terpenoids Derived from Inorganic Cyanide Martin J. Schnermann, Ryan A. Shenvi
Nat Prod Rep. Author manuscript; available in PMC 2016 Apr 1.Published in final edited form as: Nat Prod Rep. 2015 Apr; 32(4): 543–577. doi: 10.1039/c4np00109e PMCID: PMC4414506
3: Formamido-Diterpenes from the South China Sea Sponge Acanthella cavernosa Ying Xu, Jun-Hui Lang, Wei-Hua Jiao, Ru-Ping Wang, Ying Peng, Shao-Jiang Song, Bao-Hua Zhang, Hou-Wen Lin Mar Drugs. 2012 Jul; 10(7): 1445–1458. Published online 2012 Jul 2. doi: 10.3390/md10071445 PMCID: PMC3407923
4: Biological Activity of Recently Discovered Halogenated Marine Natural Products Gordon W. Gribble Mar Drugs. 2015 Jul; 13(7): 4044–4136. Published online 2015 Jun 30. doi: 10.3390/md13074044 PMCID: PMC4515607
5: Synthesis and Potent Antimalarial Activity of Kalihinol B Mary Elisabeth Daub, Jacques Prudhomme, Karine Le Roch, Christopher D. Vanderwal J Am Chem Soc. 2015 Apr 22; 137(15): 4912–4915. Published online 2015 Mar 27. doi: 10.1021/jacs.5b01152 PMCID: PMC4415034
6: Terpenoids in Marine Heterobranch Molluscs Conxita Avila Mar Drugs. 2020 Mar; 18(3): 162. Published online 2020 Mar 14. doi: 10.3390/md18030162 PMCID: PMC7143877
7: Cytotoxic Nitrogenous Terpenoids from Two South China Sea Nudibranchs Phyllidiella pustulosa, Phyllidia coelestis, and Their Sponge-Prey Acanthella cavernosa Qihao Wu, Wen-Ting Chen, Song-Wei Li, Jian-Yu Ye, Xia-Juan Huan, Margherita Gavagnin, Li Gong Yao, Hong Wang, Ze-Hong Miao, Xu-Wen Li, Yue-Wei Guo Mar Drugs. 2019 Jan; 17(1): 56. Published online 2019 Jan 16. doi: 10.3390/md17010056 PMCID: PMC6356796
8: Juxtaposition of chemical and mutation- induced developmental defects in zebrafish reveal a novel copper-chelating activity for kalihinol F Imelda T. Sandoval, Elizabeth J. Manos, Ryan M. Van Wagoner, Richard Glenn C. Delacruz, Kornelia Edes, Dennis R. Winge, Chris M. Ireland, David A. Jones Chem Biol. Author manuscript; available in PMC 2014 Jun 20.Published in final edited form as: Chem Biol. 2013 Jun 20; 20(6): 753–763. doi: 10.1016/j.chembiol.2013.05.008 PMCID: PMC3715381
9: Marine Sponges as Pharmacy Detmer Sipkema, Maurice C. R. Franssen, Ronald Osinga, Johannes Tramper, René H. Wijffels Mar Biotechnol (NY) 2005; 7(3): 142. Published online 2005 Mar 24. doi: 10.1007/s10126-004-0405-5 PMCID: PMC7087563
