Structure Database (LMSD)

Common Name
Lathosterol
Systematic Name
cholest-7-en-3β-ol
Synonyms
LM ID
LMST01010089
Formula
Exact Mass
Calculate m/z
386.354865
Sum Composition
Status
Curated


Classification

Biological Context

Lathosterol is an intermediate in the biosynthesis of cholesterol.1,2 Serum levels of lathosterol correlate with cholesterol synthesis and have been used as biomarkers of excess cholesterol production. Lathosterol accumulates in lathosterolosis, a disorder characterized by a deficiency of lathosterol 5-desaturase, the enzyme that converts lathosterol to 7-dehydro cholesterol .3

This information has been provided by Cayman Chemical

References

1. Kempen, H.J., Glatz, J.F., Gevers Leuven, J.A., et al. Serum lathosterol concentration is an indicator of whole-body cholesterol synthesis in humans. J. Lipid Res. 29(9), 1149-1155 (1988).

Reactions

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Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299
Homo sapiens (#9606)
Mammalia (#40674)
Sterols of human gallstones: the recent identification of eight different digitonin precipitable sterols.,
Gastroenterology, 1980
Pubmed ID: 7429114

String Representations

InChiKey (Click to copy)
IZVFFXVYBHFIHY-SKCNUYALSA-N
InChi (Click to copy)
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCCC(C)C)CC[C@@]4([H])C3=CC[C@@]2([H])C[C@@H](O)C1

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
SST9096
PubChem CID
SwissLipids ID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 4
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 432.37
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 7.68
Molar Refractivity 119.56

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Created at
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Updated at
26th Jan 2022