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Structure Database (LMSD)

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Common Name

Petromyzonol

Systematic Name

5α-Cholane-3α,7α,12α,24-tetrol

Synonyms

LM ID

LMST04010301

Formula

C₂₄H₄₂O₄

Exact Mass

Calculate m/z

394.30831

Sum Composition

ST 24:0;O4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Petromyzonol is a tetrahydroxy stearol which serves as the primary spawning pheromone in adult sea lamprey. It is produced in the bile of sea lamprey larvae from the bile acid precursor allocholic acid. While the adult sea lamprey is relatively insensitive to petromyzonol itself, the C-24 sulfate ester (petromyzonol sulfate) is a pheromone and a spawning chemoattractant which can be detected at very low concentrations by lamprey olfactory chemoreceptors. Petromyzonol, petromyzonol sulfate, and allocholic acid are all found in water samples from fresh water streams bearing larval lamprey populations.¹

This information has been provided by Cayman Chemical

References

1. Li, W., Sorensen, P.W., and Gallaher, D.D. The olfactory system of migratory adult sea lamprey (Petromyzon marinus) is specifically and acutely sensitive to unique bile acids released by conspecific larvae. J. Gen. Physiol. 105(5), 569-587 (1995).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Petromyzon marinus (#7757)

Hyperoartia (#117569)

Comparative studies of bile salts. Bile salts of the lamprey Petromyzon marinus L.,
Biochem J, 1969

Pubmed ID: 5810077

DOI: 10.1042/bj1140179

String Representations

InChiKey (Click to copy)

BMSROUVLRAQRBY-JLIFGLSWSA-N

InChi (Click to copy)

InChI=1S/C24H42O4/c1-14(5-4-10-25)17-6-7-18-22-19(13-21(28)24(17,18)3)23(2)9-8-16(26)11-15(23)12-20(22)27/h14-22,25-28H,4-13H2,1-3H3/t14-,15-,16-,17-,18+,19+,20-,21+,22+,23+,24-/m1/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])C[C@H](O)[C@]4(C)[C@@]([H])([C@]([H])(C)CCCO)CC[C@@]4([H])[C@]3([H])[C@H](O)C[C@@]2([H])C[C@H](O)C1