Anicequol

Anicequol
Clinical data
Other namesNGA0187; NGD-187; 16β-Acetoxy-3β,7β,11β-trihydroxy-5α-ergost-22E-en-6-one
Identifiers
  • [(3S,5S,7R,8S,9S,10R,11S,13S,14S,16S,17R)-17-[(E,2R,5R)-5,6-Dimethylhept-3-en-2-yl]-3,7,11-trihydroxy-10,13-dimethyl-6-oxo-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC30H48O6
Molar mass504.708 g·mol−1
3D model (JSmol)
  • C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1[C@H](C[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2[C@H](C(=O)[C@@H]4[C@@]3(CC[C@@H](C4)O)C)O)O)C)OC(=O)C
  • InChI=1S/C30H48O6/c1-15(2)16(3)8-9-17(4)25-23(36-18(5)31)13-20-24-26(22(33)14-30(20,25)7)29(6)11-10-19(32)12-21(29)27(34)28(24)35/h8-9,15-17,19-26,28,32-33,35H,10-14H2,1-7H3/b9-8+/t16-,17+,19-,20-,21+,22-,23-,24-,25-,26-,28+,29-,30-/m0/s1
  • Key:LWMKDRSIMLTGDK-TZEVRYHJSA-N

Anicequol (developmental code names NGA0187, NGD-187) is a naturally occurring ergostane steroid produced by Acremonium sp. TF-0356 which has nerve growth factor-like neurotrophic activity. It was under investigation by Taisho Pharmaceutical in Japan for the treatment of cognitive disorders in the 1990s, but development was discontinued and the drug was never marketed.

Chemistry

See also

References

  1. ↑ Gao SS, Li XM, Li CS, Proksch P, Wang BG (2011). "Penicisteroids A and B, antifungal and cytotoxic polyoxygenated steroids from the marine alga-derived endophytic fungus Penicillium chrysogenum QEN-24S". Bioorg. Med. Chem. Lett. 21 (10): 2894–7. doi:10.1016/j.bmcl.2011.03.076. PMID 21489788. Anicequol (3) was independently isolated from Acremonium sp. TF-0356 and was assigned the trivial name NGA0187.
  2. ↑ Nozawa Y, Sakai N, Matsumoto K, Mizoue K (2002). "A novel neuritogenic compound, NGA0187". J. Antibiot. 55 (7): 629–34. doi:10.7164/antibiotics.55.629. PMID 12243452.
  3. ↑ Hua Z, Carcache DA, Tian Y, Li YM, Danishefsky SJ (2005). "The synthesis and preliminary biological evaluation of a novel steroid with neurotrophic activity: NGA0187". J. Org. Chem. 70 (24): 9849–56. doi:10.1021/jo051556d. PMID 16292815.
  4. ↑ Williams B, Dwyer DS (2009). "Structure-based discovery of low molecular weight compounds that stimulate neurite outgrowth and substitute for nerve growth factor". J. Neurochem. 110 (6): 1876–84. doi:10.1111/j.1471-4159.2009.06291.x. PMC 2753211. PMID 19627449.
  5. ↑ "NGD 187 - AdisInsight". adisinsight.springer.com.