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Structure Database (LMSD)

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Common Name

Ecdysone

Systematic Name

2β,3β,14α,22R,25-pentahydroxy-5β-cholest-7-en-6-one

Synonyms

(22R)-2beta,3beta,14alpha,22,25-pentahydroxy-5beta-cholest-7-en-6-one
Ecdysone

LM ID

LMST01010210

Formula

C₂₇H₄₄O₆

Exact Mass

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464.31379

Sum Composition

ST 27:2;O6

Status

Curated

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Classification

Biological Context

α-Ecdysone is a prohormone of 20-hydroxy ecdysone , an insect-molting, ecdysteroid hormone.¹ The insect neurohormone, prothoracicotropic hormone, stimulates prothoracic glands to release α-ecdysone, which is then rapidly converted to its active metabolite, 20-hydroxy ecdysone.^2,3

This information has been provided by Cayman Chemical

References

1. Cherbas, L., and Cherbas, P. Distribution and metabolism of α-ecdysone in pupae of the silkworm Antheraea polyphemus. Biol. Bull. 138(2), 115-128 (1970).

2. Carrow, G.M., Calabrese, R.L., and Williams, C.M. Spontaneous and evoked release of prothoracicotropin from multiple neurohemal organs of the tobacco hornworm. Proc. Natl. Acad. Sci. USA 78(9), 5866-5870 (1981).

3. 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).

String Representations

InChiKey (Click to copy)

UPEZCKBFRMILAV-JMZLNJERSA-N

InChi (Click to copy)

InChI=1S/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22+,23-,25+,26+,27+/m0/s1

SMILES (Click to copy)

C12=CC([C@]3([H])C[C@@H](O)[C@@H](O)C[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2(O)CC[C@@]1([C@H](C)[C@H](O)CCC(O)(C)C)[H])=O