LIPID MAPS

Structure Database (LMSD)

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Common Name

ponasterone A

Systematic Name

(22R)-2β,3β,14,20,22-pentahydroxy-5β-cholest-7-en-6-one

Synonyms

25-Deoxycedysterone
Ponasterone A

LM ID

LMST01010195

Formula

C₂₇H₄₄O₆

Exact Mass

Calculate m/z

464.313791

Sum Composition

ST 27:2;O6

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Ponasterone A is an analog of 20-hydroxy ecdysone , the insect steroid hormone that regulates the metamorphosis of Drosophila.¹ Ecdysteroids such as this compound have been employed as inducers of ecdysone-inducible mammalian expression systems.^2,3

This information has been provided by Cayman Chemical

References

1. Fallon, A.M., and Gerenday, A. Ecdysone and the cell cycle: Investigations in a mosquito cell line. J. Insect Physiol. 56(10), 1396-1401 (2010).

2. Karzenowski, D., Potter, D.W., and Padidam, M. Inducible control of transgene expression with ecdysone receptor: Gene switches with high sensitivity, robust expression, and reduced size. Biotechniques 39(2), 191-192 (2005).

3. Saez, E., Nelson, M.C., Eshelman, B., et al. Identification of ligands and coligands for the ecdysone-regulated gene switch. Proc. Natl. Acad. Sci. USA 97(26), 14512-14517 (2000).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Callinectes sapidus (#6763)

Malacostraca (#6681)

Ponasterone A: a new ecdysteroid from the embryos and serum of brachyuran crustaceans.,
Steroids, 1979

Pubmed ID: 538780

Podocarpus nakaii (#453930)

Pinopsida (#58019)

Insect Hormones. The Structure of Ponasterone A, an Insect-moulting Hormone from the Leaves of Podocarpus nakaii Hay,
Chem Commun, 1966

DOI: 10.1039/C19660000915

String Representations

InChiKey (Click to copy)

PJYYBCXMCWDUAZ-JJJZTNILSA-N

InChi (Click to copy)

InChI=1S/C27H44O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h12,15-16,18,20-23,29-33H,6-11,13-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1

SMILES (Click to copy)

C1[C@@]2(C)[C@]([H])(C(=O)C=C3[C@]2([H])CC[C@@]2(C)[C@@]3(O)CC[C@]2([H])[C@]([C@H](O)CCC(C)C)(O)C)C[C@@H](O)[C@H]1O