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Structure Database (LMSD)

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Common Name

(25S)-Delta(7)-dafachronic acid

Systematic Name

(25S)-3-oxocholest-7-en-26-oic acid

Synonyms

LM ID

LMST04030222

Formula

C₂₇H₄₂O₃

Exact Mass

Calculate m/z

414.313395

Sum Composition

ST 27:3;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

(25S)-Δ7-Dafachronic acid is a sterol-derived hormone that acts as a ligand of DAF-12 with an EC50 value of 23 nM.^1,2,3,4 At 50 nM, (25S)-Δ7-Dafachronic acid inhibits the dauer-promoting activity of DAF-12, blocking the formation of infective larvae in several parasitic nematodes in favor of reproductive maturation to adults.^5,6 Thus, selective ligand modulators of DAF-12 are a potential therapeutic approach to stop larvae progression during parasitic infection.⁷

This information has been provided by Cayman Chemical

References

1. Ogawa, A., Streit, A., Antebi, A., et al. A conserved endocrine mechanism controls the formation of dauer and infective larvae in nematodes. Curr. Biol. 19(1), 67-71 (2009).

2. Motola, D.L., Cummins, C.L., Rottiers, V., et al. Identification of ligands for DAF-12 that govern dauer formation and reproduction in C. elegans. Cell 124(6), 1209-1223 (2006).

3. Martin, R., Entchev, E.V., Kurzchalia, T.V., et al. Steroid hormones controlling the life cycle of the nematode Caenorhabditis elegans: Stereoselective synthesis and biology. Org. Biomol. Chem. 8(4), 739-750 (2010).

4. Martin, R., Däbritz, F., Entchev, E.V., et al. Stereoselective synthesis of the hormonally active (25S)-Δ7-dafachronic acid, (25S)-Δ4-dafachronic acid, (25S)-dafachronic acid, and (25S)-cholestenoic acid. Org. Biomol. Chem. 6(23), 4293-4295 (2008).

5. Beckstead, R.B., and Thummel, C.S. Indicted: Worms caught using steroids. Cell 124(6), 1137-1140 (2006).

6. Wang, Z., Zhou, X.E., Motola, D.L., et al. Identification of the nuclear receptor DAF-12 as a therapeutic target in parasitic nematodes. Proc. Natl. Acad. Sci. USA 106(23), 9138-9143 (2009).

7. Sharma, K.K., Wang, Z., Motola, D.L., et al. Synthesis and activity of dafachronic acid ligands for the C. elegans DAF-12 nuclear hormone receptor. Mol. Endocrinol. 23(5), 640-648 (2009).

String Representations

InChiKey (Click to copy)

SQTAVUCHOVVOFD-OBRBSRNPSA-N

InChi (Click to copy)

InChI=1S/C27H42O3/c1-17(6-5-7-18(2)25(29)30)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h9,17-19,22-24H,5-8,10-16H2,1-4H3,(H,29,30)/t17-,18+,19+,22-,23+,24+,26+,27-/m1/s1

SMILES (Click to copy)

C1CC(=O)C[C@]2([H])CC=C3[C@@]([H])([C@]21C)CC[C@]1(C)[C@@]([H])([C@H](C)CCC[C@H](C)C(=O)O)CC[C@]13[H]