Anicequol

Anicequol (developmental code names NGA0187, NGD-187)[1] is a naturally occurring ergostane or lanostane steroid produced by Acremonium sp. TF-0356 which has nerve growth factor-like neurotrophic activity.[2][3][4] 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.[5]

Anicequol
Clinical data
Other namesNGA0187; NGD-187; 16β-Acetoxy-3β,7β,11β-trihydroxy-5α-ergost-22E-en-6-one
Identifiers
IUPAC name
  • [(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
ChEMBL
Chemical and physical data
FormulaC30H48O6
Molar mass504.708 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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

Chemistry
See also: List of neurosteroids

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.
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