Lathosterol

Chemical compound From Wikipedia, the free encyclopedia

Lathosterol is a cholesterol-like molecule found small amounts in humans.[1] The enzyme Δ7-sterol 5(6)-desaturase converts it to 7-dehydrocholesterol. It is accumulated in lathosterolosis.[2]

Quick facts Names, Identifiers ...
Lathosterol
Ball-and-stick model of lathosterol
Names
IUPAC name
5α-Cholest-7-en-3β-ol
Systematic IUPAC name
(1R,3aR,5aS,7S,9aS,9bR,11aR)-9a,11a-Dimethyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,5a,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • 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 checkY
    Key: IZVFFXVYBHFIHY-SKCNUYALSA-N checkY
  • InChI=1/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
    Key: IZVFFXVYBHFIHY-SKCNUYALBG
  • O[C@H]1CC[C@@]2([C@@H]3\C(=C/C[C@H]2C1)[C@@H]4CC[C@H]([C@H](C)CCCC(C)C)[C@]4(CC3)C)C
Properties
C27H46O
Molar mass 386.65 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis

The final step in the biosynthesis of lathosterol is by reduction of the double bond in the sidechain of the sterol 5α-cholesta-7,24-dien-3β-ol when acted on by the enzyme Δ24-sterol reductase, which uses nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.[3][4]

2D representation of the chemical structure of Q27101835.
5α-cholesta-7,24-dien-3β-ol
+ NADPH
 
 
H+
 
Reversible left-right reaction arrow with minor forward substrate(s) from top left and minor reverse product(s) to bottom left
H+
 
 
2D representation of the chemical structure of lathosterol .
lathosterol
+ NADP+
 

In cholesterol biosynthesis

In vertebrates, lathosterol is an intermediate in the pathway to cholesterol via 7-dehydrocholesterol.[5][6][7] The enzyme Δ7-sterol 5(6)-desaturase catalyses the oxidation reaction:

2D representation of the chemical structure of lathosterol.
lathosterol
+ 2 Fe2+ + 2 H+
 
 
O2
2 H2O
Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left
O2
2 H2O
 
7-dehydrocholesterol
+ 2 Fe3+
 

It uses two molecules of the cofactor ferrocytochrome b5 with two protons and one oxygen for each molecule of lathosterol converted.[5]

See also

References

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